Moral Event Horizon

"Further than anybody. And I thought I knew what that meant, though the Death Eaters did not. He was referring to his Horcruxes, Horcruxes in the plural, Harry, which I do not believe any other wizard has ever had. Yet, it fitted: Lord Voldemort has seemed to grow less human with the passing years, and the transformation he has undergone seemed to me to be only explicable if his soul was mutilated beyond the realms of what we might call usual evil."

- Professor Albus Dumbledore regarding how far Lord Voldemort could have gone crossing MEH as he creates Horcruxes.

The "Moral Event Horizon", or "MEH" for short, refers to an action by wrongdoer that is so vile that it usually eliminates audience sympathy for the villain and makes it clear that they are unrepentantly evil and will not be redeemed, unless if they themselves are offended by the actions of another villain, or admit themselves that they are beyond redemption.

Whilst popularized by TV Tropes, this term not gained its name from that site, but rather from the scientific fact that nothing can escape a black hole is referred to as the boundary of the region from which no escape is possible and is known as the event horizon, hence the name. A villain who crosses the horizon, or enters the black hole, has no hope of escaping except under extremely rare, extraordinary circumstances. All villains who fall under Pure Evil are by definition beyond the Moral Event Horizon. However, crossing the Moral Event Horizon does not necessarily make a wrongdoer Pure Evil, it only means that they are irredeemably evil. Some villains have or almost crossed the Moral Event Horizon, or done something despicable enough to make the fans believe they did so, only to later redeem completely or partially.

A strong example of a Purely Evil villain would be either a villain who (in addition to having no or a very poor excuse for being evil) commits multiple especially heinous Moral Event Horizon-worthy deeds, or if the line in question proves to be heinous enough. The notable consequence on the villains' reputation whom crosses MEH would led either Unspeakable Evil mere mention of their name as a taboo and believed to bring bad luck to those who utter it (or in extreme causes disease, death, or other preternatural curses) or they themselves becoming Damned Souls when they died. By definition, a character can only cross the Moral Event Horizon once; however, it is possible for a villain to have more than one event as a potential Moral Event Horizon, such as the various adaptations of the Joker of DC Comics and Teridax of BIONICLE. Other villains have more than a potential and often leave an impact on the public that they do wicked things all the time and commit Moral Event Horizon acts like a hobby, such as Lord Voldemort, Sir Isaac Ray Peram Westcott, Emperor Palpatine and Emperor Tathagata Killer.

These characters are almost invariably Pure Evil.

 IMPORTANT NOTE: Listed below are things that should not be added on the list of MEHs: 


 * Fanon examples, as they would confuse the reader.
 * Certain flawed actions that done by characters that confirmed not evil nor antagonistic won't be ever counted as act of MEH if the said actions not officially put them to the dark side or merely portrayed them as flawed hero.
 * Acts of MEH are usually driven by malicious intentions that make the villain cruel enough to be taken seriously by heroes and other villains who are outright appalled by the said actions.

A Song of Ice And Fire

 * Ramsay Snow: Torturing Theon Greyjoy for pleasure to the point that he ends up forgetting his identity and going insane, renaming him "Reek" and making him his passive slave. He even castrates him (though this occurred only in TV series).
 * Joffrey Baratheon: Ordering the beheading of Ned Stark and torturing Sansa with this throughout the series.
 * Cersei Lannister: If it's not by ordering that Tyrion (her brother) be arrested for Joffrey's murder, it's the unscrupulous pleasure she receives and makes no effort in hiding when Oberyn is killed and fails to win Tyrion's freedom in the trial by combat.
 * Petyr Baelish: If he crosses it, it's by betraying Ned and helping the Lannisters maintain the Iron Throne (which could qualify for almost anyone who refuses to cross the Lannisters when in the position to do so). He also caused Ned's death, unbeknowest to everyone, and later he left Tyrion in the cell after poisoning Joffrey and pushed Lady Arryn out from the Moon Door after hinting that he never loved her, braking her life and mind.
 * Tywin Lannister: Mistreating his son Tyrion throughout his life, going so far as to rape his wife, Tysha, and lie to Tyrion that she was a whore.
 * Gregor Clegane: Burned his brother's face when he was a child.
 * Stannis Baratheon: In one of the most famous moral event horizons ever, after losing men, food, and supplies in his siege on Winterfell, he burned his beloved daughter, Princess Shireen, at the steak to appease The Lord of Light and grant him victory (TV series only).
 * Walder Frey: Initiating the Red Wedding, which results in the sacking of the Stark army. By extension, the pregnant Talisa's brutal death and the murder of Robb Stark and his mother.
 * Roose Bolton: Betraying the Stark army, assisting Walder Frey in the Red Wedding, and killing Robb Stark.
 * The Night King: Kills nearly every inhabitant of Hardholme village and resurrects them as undead, later kills the Three-Eyed Raven, and much later kills the Dragon Viserion, and resurrects him as an undead dragon.

A​vatar: The Last Airbender/Legend of Korra

 * Sozin: He abandoned his old friend, Avatar Roku, to die in lava so he could no longer disturb his plan of conquering the world and annihilate all Air Nomads, save for Avatar Aang because he could never find him. The damage was so great that remnants of Air Nomads still rebuilding their civilazation by the era of Avatar Korra.
 * Fire Lord Ozai: He has several possible contenders: After his son Zuko disrespected one of Ozai's generals, the Fire Lord burnt the boy's face, leaving Zuko with a scar on his eye. After Zuko scolded his father for this years later, Ozai threatened to kill his son with lightning. Otherwise, in the finale, he appoints his daughter Azula as Fire Lord... but seconds later, Ozai tells her that the position is powerless. In the comic series, "The Searching", Ozai revealed his sadistic nature to his wife Ursa when he told her that he'll abuse Zuko as if he was the son of Ursa's lover, Ikem, in order to punish her for missing her lover despite Zuko being Ozai's son and doing nothing to deserve this. In either way, Ozai's atrocity against both Zuko and the entire world ultimately haunted Zuko in his early days as a Firelord, to the point that he almost ruined both his life and his bond with his allies and friends (especially Aang) out of fear of turning to the dark side as far as Ozai ever did.
 * Admiral Zhao: He killed the spirit of the Moon to weaken waterbenders and ensure his victory. It's revealed that in Book 2 of "Avatar: The Legend of Korra" that as punishment for this MEH, Zhao's soul was imprisoned by La in the Fog of Lost Souls not long after the spirit of the Moon revived and by the time Aang's children ventured inside to find Jinora, Zhao had entered the madness state.
 * Long Feng: He crosses this by immediately killing Jet in cold blood just as Jet shrugged off his brainwash influence. If this was not enough, he may have truly crossed the MEH completely by conspiring against the Earth King along with the Dai LI and imprisoning and brainwashing the inconvenient witnesses. Worse, as the last ditch to complete his plans, he resorts to manipulate Azula to help him retake Ba Sing Se for himself, only for this deed to backfire as she beats him in his own manipulating game in the end.
 * Dai Li: They conspired against the Earth King under Long Feng's command, imprisoned and brainwashed the inconvenient witnesses, and also betrayed both the Earth Kingdom and Long Feng when they joined Azula and helped her take over the kingdom. With no hesitation they destroyed the walls of Ba Sing Se so the invasion forces of the Fire Nation could conquer the city with no problem.
 * Hama: She imprisoned innocent villagers with her bloodbending and took over the bodies of Sokka and Aang to force Katara to use bloodbending against her, making her a bloodbender.
 * Amon: He terrorized and conquered Republic City, stripped many people of their bending, including Avatar Korra, and also tried to destroy the last hopes for restoration of airbending.
 * Hiroshi Sato: Unable to cope with the fact that his daughter Asami still protected benders as not all of them are evil, he eventually succumbed to his hatred against benders and tried to kill his own daughter because he thought "there was no chance to save her". Though he failed, thanks to Bolin, he still made it clear he was going to try and kill her.
 * Tarrlok: His fear of Amon caused him to misuse his authority to arrest non-benders. He also imprisoned Avatar Korra through forbidden bloodbending and turned against the rest of the Republic City Councilors.
 * Unalaq: He framed his brother to take his place as a candidate for Chief of the Northern Water Tribe, manipulated his own niece, Avatar Korra, to fulfill his plans, started a war between the Water Tribes, took Jinora as a hostage and threatened to destroy her soul to force Avatar Korra to help him, and freed Vaatu, the most chaotic spirit of the universe.
 * Zaheer: He, along with his crew, attacked the newly reborn Air Nation to force Korra to surrender, cornered the Air Nation (except Kai) from escaping, and brutally beaten up Tenzin. Later, he went back on his words by luring Korra's friends into a trap and keep the airbenders as prisoners. After he managed to capture Korra, he had her poisoned to force her into the Avatar state and kill her to end the Avatar cycle. Though he failed in this, he managed to temporarily have her both in a depressed and wheelchaired state as well as responsible for unintentionally creating a hallucinogenic entity in Korra's mind as result of scarring her mentally. After being imprisoned, on the other hand, he later regretted his actions after a new dictator started to begin her own empire, which is why he undid the damage he caused on Korra as the redemption of his said MEH crossing actions.
 * Kuvira: She first crossed it by attempting to kill Korra after defeating her, then ordered her army to attack after Opal and Jinora intervened. After finding out about Zhu Li sabotaging the cannon during a weapon test, she had her chained up in an abandoned city where the cannon was aiming at, and she did not hesitate to use her giant mecha-suit to fire at the building where her fiancee, Baatar Jr., was held prisoner in.

Batman

 * Ra's al Ghul: In Batman Begins, he sets Wayne Manor on fire, almost killing both Bruce Wayne and Alfred Pennyworth.
 * Bane: In The Dark Knight Rises, he bombed the Gotham City Football Stadium, which kills hundreds, and furthermore holds the entire stadium hostage, proclaiming the existence of a nuclear bomb within the city's limits before snapping the neck of Dr. Leonid Pavel in front of all of them. He may have crossed it earlier when he broke Batman's back.
 * Talia al Ghul: It is revealed that she was the mastermind behind the plan of conquering and destroying Gotham City.
 * Poison Ivy: In Batman & Robin, she crosses it when she cut off Nora Fries' life support, leaving her for dead and then lying to Mr. Freeze, saying that Batman and Robin killed her so that he will freeze all of Gotham City in a rage.
 * Joker: Kidnapped Harvey Dent and Rachel Dawes and put them in buildings set to be blown up, leading to the latter dying and the former becoming Two-Face. This in turn causes Batman to "break his one rule" and become a wanted criminal.
 * Penguin: Although he has a tragic backstory (being abandoned by his parents, thrown in a sewer, and left to die), he has killed many innocent children of aristocrats and later tries to kill Chip (the son of Max Shreck).
 * Joker: He killed Bruce Wayne's parents (instead of Joe Chill in the comics) and later attempts to kill all the citizens of Gotham using his poison gas. Thankfully, he is stopped by Batman.
 * Joker: Has many candidates for these:
 * "The Last Laugh": He covers Gotham City in a cloud of laughing gas, which is revealed to eventually cause permanent insanity if not removed, and begins plundering the crazed city.
 * "Joker's Favor": He spends years stalking and threatening Charlie Collins after a single slight and forces him to help him pull of a crime by threatening to murder his family.
 * "Mad Love": Physically and emotionally abuses Harley for capturing Batman simply because he wanted to do it himself. He eventually decides to take Harley's advice and simply shoot Batman on the spot, despite the fact that he berated her for that suggestion.
 * "Harlequinade": He steals an atomic bomb and tries to blow up Gotham, and it's also revealed how he manipulated Doctor Harleen Quinzel (Harley Quinn) to join him.
 * "Beware the Creeper": Tosses straitlaced newsman Jack Ryder into a mixture of chemicals and mutates him into the crazed Creeper. He created a hero, but nearly ruined his life.
 * "Be a Clown" He tries to bomb the mayor's son's birthday party, which could have killed the party-goers as well (some of which were children).
 * "Return of the Joker": Kidnaps Robin (Tim Drake) and tortures and brainwashes him for weeks via shock torture and serum injections until he gave away all his secrets to the Joker. He was driven insane and renamed "Joker Junior", which enrages Batman so severely that he threatens to kill him. Shortly after, Joker was killed when Robin shot him with a trick BANG gun. In the edited version, Robin pushes Joker into the shock treatment room where he then slips, accidentally turns on an electrode, and electrocutes himself. This is by far the most evil act Joker has ever done in the animated series, worsened by the fact that it's later turned out that he has implanted a chip inside Tim Drake's head that contained his mind and allowed him to possess the poor Robin later on, as when Drake killed him, he only killed Joker's own lifeless husk.
 * Roland Daggett: Crosses it by trying to blow up Crime Alley, which would have resulted in the deaths of several people if his plan was successful.
 * Arkady Duvall: Crosses it by violently assaulting (and possibly raping) a woman, abusing his henchmen, and trying to sabotage a train.
 * Sewer King: Crosses it with his horrific treatment of the children in his care. Batman was tempted to kill him out of disgust for his crimes.

Bionicle

 * Makuta Teridax: Crossed the Moral Event Horizon throughout the entire storyline of the entire series, thus making him into the deeper part of the MEH:
 * Usurped Makuta Miserix's leadership after his corruption, also have Gorast executed a Makuta member for going against his plan in front of the other members of the Brotherhood of Makuta.
 * Launched the attack on the island of Artakha, mortally wounded Mata Nui in a fight and successfully steal the Kanohi Avohkii.
 * Kidnapped Turaga Dume and placed him inside the Matoran Sphere.
 * Falsely framed Toa Vakama and the other Toa Metru of being an imposters.
 * Ordered the Vahki to command all the Matoran to go to the Coliseum to be placed inside the Matoran Spheres so that he can brainwashed them.
 * Wrecked the power source of Metru Nui, killed Nivawk, Nidhiki and Krekka.
 * Killed Turaga Lhikan when he tried to save Vakama from death.
 * Wounded the Shadowed One in the fight and aging him.
 * Filled Ahkmou's mind with lies, making him believe that both Toa and Turaga are "evil".
 * Brainwashed all the Rahi with infected Kanohi Masks, causing them to attack both the Tuaga and the Matoran.
 * Sent the six Rahkshi to destroyed both Ta-Koro and Onu-Koro in order to find the Kanohi Avohkii.
 * Manipulated the Piraka's minds with his powers into going to Voya Nui, using them to brainwash all the Matoran there.
 * Absorb Gali's spirit into his body, though her spirit got out later.
 * Umarak: Crosses it when he threatened to drop Ketar off the cliff in front of Pohatu. He crossed again when he mortally wounded Gorast in the final battle when she tried to take the Mask of Control from his face.

Black Butler

 * Angela Blanc/Ash Landers: In the anime, Ash/Angela is truly responsible for the arson in the Phantomhive Manor. The fallen angel also ordered its minions to brought Ciel to its cult for some evil purpose to purge the world.
 * Angela controlled Drossel Keinz with a puppet and lured many girls to her trap, including Elizabeth. She ordered Drossel to make dolls with these girl's body and had no care with these "toys". When Ciel confronted her, Angela sewed Ciel's parents' corpses into a hideous creation she controlled to kill Ciel. After Ciel destroyed the monster, Angela sadistically mocked Ciel that it was he who caused his parents' "second death". **Before the finale of the Season 1, as soon as Ash found out Queen Victoria started to rot and refused to leave, insetead of curing the Queen, Ash left Buckingham Palace and flew for the burning London. Then, Ash sets off to the bridge, which is built out of the human sacrifices and soul, to which Sebastian comments that it cannot possibly be a holy bridge.
 * Doctor: After revealing the true material of the limbs are children's bones and scolding by Joker, Doctor pulls a brainwashed, kidnapped child that Baron Kelvin had locked up and drags her over to the sacrifice table. Maniacally, he grabs a knife and proceeds to slay her.
 * Major Hilde Dickhaut: She has great hostility towards Phantomhive household, and this hostility drove her mad. After revealing her true nature to the manga readers, Hilde orders Wolfram, Anne, and Grethe to kill Sieglinde if she left the Witch Forest before she can be retrieved, causing massive chaos. Later, while suffering Villainous Breakdown, Hilde shot Wolfram and nearly killed him, mocking him as "traitor". She then attempted to kill everyone even included Sieglinde, but fortunatly, she was soon stopped and killed by Sebastian on time.
 * Former Head Trancy: He sexually abused many slave boys in his manor, including his adoptive son Alois Trancy, making the old man one of the most depraved and hated person in whole franchise.
 * Grell Sutcliff: She sliced Angelina Durless in dismay after she refused to kill Ciel.
 * Hannah Anafeloz: She swallowed the soul of Luka Macken and caused the tragedy of Alois.
 * Professor Sullivan: Being the true main antagonist of Green Witch arc and the birth mother of Sieglinde Sullivan, she faked the legend of werewolves for using her daughter's cleaverness to achieve her evil plan of making the ultimate toxic bombs, which might cause losses everywhere on Earth.
 * Derrick Arden: Secretly bullying his classmates with his gang and took their works of talents under his own credit, fueling the murder attempt of Edgar Redmond, Lawrence Bluher, Herman Greenfil and Gregory Violet.

Bleach

 * Sōsuke Aizen: Betrayed and plotted against Soul Society, tried to execute Rukia to take Hogyoku from her heart, murdered his officials, put everyone in an incredible illusion, created an army of Arrancars, attempted to slaughter 100,000 humans to create a key to the castle of the king of Soul Society, singlehandedly crippled the whole elite army of Soul Society, tried to kill Ichigo Kurosaki's friends simply to mock him, and also slashed Tier Harribel when he saw her no longer useful.
 * Kaname Tōsen: Betrayed Soul Society along with Aizen and attempted to kill the ones who respected him the most, Hisagi and Komamure.
 * Mayuri Kurotsuchi: He tortured and killed nearly all the Quincy, turned some of his subordinates into human bombs and detonated the sole survivor because "bombs aren't supposed to come back", and casually showed Uryu a picture of his grandfather's body.
 * Nnoitra Gilga: Betrayed Nelliel and crippled her, attempted to kill Ichigo Kurosaki, and psychically abused Orihime.
 * Jin Kariya: Invaded Soul Society and tried to wipe it out along with all inside.
 * Muramasa: Started a rebellion against Soul Society and manipulated Ichigo.
 * Shūkurō Tsukishima: He manipulated Ichigo and brainwashed all his family and human friends to turn them against him.
 * Kagerōza Inaba: Created an army of duplicates of the Soul Society army and used them to conquer Soul Society.
 * Yhwach: Started a war between the Quincy and Soul society and murdered General Yamamoto. he also nearly destroyed reality in his quest to obtain godhood.

Dragon Ball

 * Mercenary Tao: The first truly evil villain of the series, Tao makes a profit out of slaughtering people, regardless of gender or age. After killing Upa's father, Bora, he then goes on to curbstomp Goku and would have killed him had it not been for his Grandpa's Dragon Ball shielding him from the attack. He then commits his most heinous act when he forces a tailor to overwork on making a new outfit for him, and then murders him when the tailor asks him to pay for it. Even after being defeated by Goku and turned into a cyborg, he shows he is still as ruthless as ever when he stabs and tries to blow his old student Tien Shinhan up along with everyone in the Tenkaichi Budōkai stadium.
 * King Piccolo: Crosses it when he orchestrates the deaths of every Tenkaichi Budōkai participant, beats Goku to within an inch of his life, and murders Master Roshi, Chiaotzu, and even Shenron, thus preventing anyone from using the Dragon Balls against him. He then proceeds to take over the world and announces that West City, Bulma's hometown, will be destroyed within 24 hours as part of an annual culling of humanity.
 * Dodoria: Crosses it when he betrays and kills Bardock's entire squad on Planet Meat. He later murders Dende's brother Cargo with an Energy Cannon before breaking Elder Moori's neck.
 * Frieza: Crosses it when he destroys Planet Vegeta and most of the Saiyan race, who were nothing but loyal to him. He later kills every single Namekian on Namek even after finding out where the Namekian Dragon Balls are, mortally wounds Nail, and kills Dende, Vegeta and Krillin in very brutal fashions, planning to do the same thing to Son Gohan and Goku as well. He also refuses to abandon his evil ways, even after Goku spares his life.
 * Cell: Crosses it when he murders countless civilians by brutally sucking the life energy out of them through his tail. He also causes Gohan to go Super Saiyan 2 by not only torturing all of his friends, but also killing Android #16 in front of him.
 * Vegeta is a very special case. He started out as a ruthless mass murderer interested only in power, and crossed many lines by killing or abusing Goku's friends (and his own), Namekians, many innocent people (under Babidi's control), and acting selfish to his friends and family. By redeeming himself after all this, he can be considered as a Karma Houdini. However, all his victims were resurrected (and later when reviving Buu's victims, Vegeta wants to make sure his victims were revived as well), he was raised by Frieza to be a killer, and Vegeta eventually performed a heroic sacrifice. Therefore, his crossing of the Moral Event Horizon is very debatable.
 * King Vegeta: Crosses it when he has the entire Tuffle race massacred, just so that the Saiyans can take over their planet. He later orders his men to execute Paragus and his infant son Broly after finding out that the latter was the Legendary Super Saiyan.
 * Broly: Crosses it when he blows up the planet that his father's slaves had previously lived on, just to see how they would react.
 * Spopovich: Crosses it when he pummels Videl to within an inch of her life at the 25th Tenkaichi Budōkai, just to get back at Mr. Satan for beating him at the previous tournament.
 * Van Zant: Crosses it when he kills several innocent bystanders and tries to kill Mr. Satan and Bee, which results in the creation of Evil Buu.
 * Tambourine: Crosses it when he murders Krillin, Nam, King Chappa, Giran, Bacterian, Man-Wolf and Pamput as part of King Piccolo's evil plan.
 * General White: Crosses it when he threatens to kill the elder of Jingle Village then shoots Goku, almost killing him. This ends up causing Android #8 to fully overcome Dr. Gero's malicious programming and save Goku by punching White through a wall, sending him falling to his death far below.
 * Dr. Gero: Crosses it when he kidnaps a pair of teenagers and forcibly converts them into Android #17 and Android #18. He then creates the biomechanical android Cell as part of his revenge scheme against Goku, who had indirectly caused the death of his son.
 * Commander Red: Crosses it when he reveals that he plans on using the Dragon Balls to make himself taller, regardless of how many of his men die attempting to find them. This revelation causes Staff Officer Black to kill him by shooting him through the head.
 * Super Buu: Crosses it when he unleashes the Human Extinction Attack, killing almost every living being on Earth. He then murders everyone on Kami's Lookout for his own personal amusement.
 * Kid Buu: Crosses it when he destroys the Earth using his Planet Buster Bomb, before attempting to kill every being in Universe 7, living or dead.
 * Bojack: Crosses it when he kills Zangya, who was nothing but loyal to him, just because she showed fear after seeing Gohan go Super Saiyan 2 in front of them.
 * Goku Black: Crosses it when he kills Chi-Chi and Goten by decapitating them with an Energy Blade.
 * Zamasu: Crosses it when he attempts to destroy all of reality by physically merging with it in his Infinite Zamasu form.

​Digimon

 * Devimon: Turned several Digimon evil via Black Gears.
 * Myotismon: He is always been darker than Devimon and Etemon, threatening to kill many innocent children in his search for the eighth Digidestined, but he crossed the line when he murdered Gotsumon and Pumpkinmon for their desertion then later reinforcing it by killing Wizardmon. He also took over the body of Yukio Okiwa and took 3 years from his life.
 * After taking the form of VenomMyotismon by cannibalizing his remaining minions via his bats, Myotismon inhales and devoured DemiDevimon, who helped him to be resurrected with enough additional energy, in order to empower himself and, more vitally, because DemiDevimon had became useless.
 * After taking the form of MaloMyotismon, Myotismon psychologically tortured Arukenimon and snapped her neck. When an enraged Mummymon turned against him and attempted to revenge for Arukenimon, Myotismon destroyed him with Crimson Mist.
 * Puppetmon: He kills his own henchman, who was begging to be taken with him.
 * Machinedramon: He orders to destroy his city just to ensure the deaths of the Chosen Children, enslaves hundreds of Numemon, expresses desire to kill Kari as painfully as he can, and massacres the aforementioned Numemon when they try to stop him.
 * After becoming Millenniummon he splits Digiworld in half, petrifies Tai and Agumon, infects ken with a dark spore which becomes the catalyst for him becoming the Digimon Emperor, and reduces an alternate Digiworld to a near lifeless husk.
 * Piedmon: He conquered and destroyed the Digital World and changed it into his own kingdom. He also turned most of the heroes into keychains.
 * Beelzemon: He sends Takato into a ballistic rage when he kills Leomon and therefore sends Jeri, his tamer, into despair.
 * Lucemon: He crosses the line with his plan to enslave the residents of the Digital World, strip them of their free will, and force them to obey him. Also, in his Chaos Mode, he kills Loweemon and then absorbs Koichi's data as Koichi sacrifices himself against his Ultimate Sacrifice attack. He eventually moves on to try to enslave the human world as well.
 * Apocalymon: He crosses it when he crushes the Crests of children and sends them to another dimension. He also attempted to annihilate the real and digital worlds.
 * Kurata: Crosses it by using the Gizumon units to commit genocide on the Digital World, then kills Keenan's surrogate father Digimon, Merukimon, and sadistically taunting him about it. This action is arguably one of the worst in the series.
 * Bagramon: He successfully conquers the Digital World and turns it into his empire. He also absorbs his brother to become stronger and to conquer the human world.
 * DarkKnightmon: He turned Yuu on his side by lying to him when he was just a naive child.
 * NeoVamdemon: He uses the darkness loader to absorb MetalGreymon and become stronger off of his life force.
 * Gravimon: He uses his whip to torture Christopher's mind and attempts to make him his mindless puppet. He also caused Deckerdramon's tragic sacrifice.
 * King Drasil: In the film "X-Evolution", he unleashes a virus that kills 95% of the population of the digital world, orders the royal knights to hunt down Digimon who survived this, and tries to destroy the digital world. In "Digimon Savers", he decided to destroy the human world to save the digital world from collision, but in reality he wanted to destroy humans so they could no longer affect the evolution of Digimon.

Horror/Monsters/Thrillers/Slashers

 * Count Orlok: He crosses it when he delivers the plagues to the town of Wisborg and kills many people, including Ellen Hunter, Thomas Hutter's wife.
 * Michael Myers: Though at first he appears to simply be mentally disturbed when he kills his older sister, it is proven that he is the embodiment of evil when he kills innocent people in sadistically gruesome ways (without a sign of pity, regret, or any other type of emotion) that stand in his way from killing his entire family, especially Dr. Samuel Loomis.
 * Freddy Krueger: Murdered 20 children and killed his wife Loretta in front of his daughter when she discovered he was the Springwood Slasher. He also trapped several teenagers inside his body so that he could harness their souls for energy.
 * Jason Voorhees: Though his backstory of him being born deformed, mentally disabled, and then nearly drowning in the camp lake makes him sympathetic, Jason slaughtered countless people without a sign of pity, regret, or any other type of emotion.
 * Roman Bridger: It is discovered he convinced Billy to kill Maureen Prescott in the first place, setting the events of the entire Scream franchise in motion.
 * Otis B. Driftwood: He tortured people, and then killed them without remorse with the help from his family.
 * Captain Spaulding: He threatens to kill a young boys family because the boy doesn't like clowns, and he helped the Firefly family kill people.
 * Baby Firefly: Like her brother Otis, Baby tortured a bunch of people, and then killed them without remorse.
 * Billy Loomis: Continues his murder spree with Stu, even though his revenge on Maureen Prescott was complete.
 * Jill Roberts: Kills her own friends, mother, and betrays her own partner/lover Charlie via killing him so she can become the sole hero of the murder spree she started.
 * Jack Torrance: Physically abuses his son once, verbally abuses his wife multiple times, later tries to kill both of them with an ax, and actually succeeds in killing Dick Hallorann.
 * Pazuzu (The Exorcist) : He crossed it when he attempts to kill Regan MacNeil.
 * The Entity: While under it's prominent chosen form as Freddy Krueger, it has crossed the MEH when it started to kill innocent people and children (such as Heather Langenkamp's husband) and he almost killed Heather and Dylan.
 * Dr. Christopher Meddows: Crossing it by launching his germ warfare prototype onto a small town, and when it mutated into The Blob decides to test its military potential by quarantining the town and running experiments on the survivors. When Meddows orders the Blob to be trapped in the sewers, he seals some of his own men with it.
 * Anton Bartok: Either crosses it when he lies to Veronica about her baby not being mutated to see the results of it's birth, causing Veronica to die of cardiac arrest, or keeping a mutant dog alive and in pain in a pit, lying to Martin that it was immediately put to sleep.
 * Godzilla: Despite being the protagonist of the series, he usually crosses it a long of times when he deliberately wrecked havoc on Tokyo, killing million of humans.

How To Train Your Dragon

 * Drago Bludvist: In a flashback featured in the second film, he had armored dragons burn down a longhouse full of Vikings leaving Stoick as the sole survivor.
 * Alvin the Treacherous: Threatening the lives of Heather's parents to goad her to his side.
 * In the book series, he betrayed Hiccup and Fishlegs, and tried to have them eaten by the Monstrous Strangulator.
 * Johann: He killed real merchants and stole the credit of their accomplishments, and tried to kill anyone and destroy any island in his way.

Middle-Earth Saga

 * Smaug: Immediately crossed the MEH when he robbed the dwarf race of their kingdom and their treasure hoard, forcing them out of their kingdom and making them homeless and murdering many dwarven races and all their guards and warriors, massacred Lake-town and has never been remorseful for his cruel, evil actions and gleefully talks about them as a reminder to his enemies of his capabilities for being impenetrable, vile and cataclysmic.
 * Sauron: Killed Elendil, King of Gondor and Gil-galad, returned after his defeat and regathered his armies and strength under the nose of Middle-earth, defeated and imprisoned Gandalf the Grey upon the discovery of his return, tortured Gollum for information on the whereabouts of the One Ring.
 * Azog the Defiler: Brutally crossed it when he murdered the dwarf king, Thror, and many other races of dwarves, nearly killed Thorin during An Unexpected Journey and then in The Battle of the Five Armies, he killed Thorin's nephew, Fíli and later mortally wounded Thorin during the Battle of Five Armies and each time, showed nothing more than a sadistic smile whenever committing these kind of acts, considering that he is "the most vile of the orc race".
 * Saruman the White: While he acted as a double-agent for the Dark Lord Sauron during The Hobbit, he crosses the MEH during The Lord of the Rings when he betrays the White Council and Gandalf to Sauron's forces and is then pinned at the MEH when he creates bread of darkness known as the Uruk-Hai and under his command, they terrorized countless cities of Middle-earth (including the kindom of Rohan), intending to wipe out the race of mankind.
 * Glaurung: Glaurung possibly passes the MEH when he convinces Turin that he needs to rescue his family when they were in no peril and abandoning Findiluas to his death, later laughing afterwards. He possibly passes it again when he sends Nienor into amnesia. He certainly passes it when with his last breath, he lifts his amnesia spell from Nienor and reveals that she is Turin's brother and that she is carrying their child, resulting in the suicide of Nienor, Turin, and the death of an unborn child and Glaurung had no qualms about gloating about it.
 * Bolg: Wounded Kili with a poisonous arrow and killed numbers of elves and dwarves during many battles, including the Battle of Five Armies, where he killed Kili.
 * Gríma Wormtongue: Crossed this when he betrayed Rohan to Saruman and manipulated king Théoden of Rohan until being foiled by Gandalf, whom revived as White Wizard.
 * Denethor: Secretly used a Palantír to probe Sauron's strength.
 * Gollum: Crossed it when killed own cousin for the One Ring and tricked Frodo into trusting him, so he could trap and double-cross him.

My Little Pony: Friendship Is Magic

 * Discord: Is an interesting case. He appeared to have crossed it in "The Return of Harmony" by cheating at his own game, corrupting the main characters, breaking their friendship, and bringing chaos throughout the land, taking sadistic glee in it all the whole while.
 * In later seasons, the Mane 6 work their hardest to redeem him. In "Keep Calm and Flutter On", he reveals that he had only tortured the ponies out of self-defense, so Fluttershy offers to keep Discord's evil in check. Discord pretended to be Fluttershy's friend, which he did so well that it really worked.
 * In Twilight's Kingdom, he almost crosses the MEH when he betrays all of Equestria when Tirek tempts him to join forces with him. When Tirek drains Discord of his magic, Discord notices how betrayed Fluttershy feels. He instantly regrets having turned against his only friends. Once Tirek is defeated, and everyone's magic is restored (even Discord's), Discord honestly admits that friendship is the most important magic of all.
 * Teenage Dragons: After bullying Spike throughout Dragon Quest, they finally cross the line when they plan to smash phoenix eggs and eat them.
 * Queen Chrysalis: When she impersonated Princess Cadance, leaving her to die in the forgotten caves beneath Canterlot, Twilight Sparkle was the only one who noticed a change in personality and called her evil, which causes her brother (who was her "big brother best friend forever" and never once had a single fight with her), her mentor (who only got angry at her once before, when she caused eternal chaos, and remained understanding and forgiving even then), and her friends (whose friendship was so powerful it defeated two mighty foes) to turn against her and disown her of their own accord (as opposed to Discord corrupting them to turn them against one another). This was arguably the most depressing moment of the series. However, many feel her true crossing of the Moral Event Horizon occurred in the comics, whose canonocity is up to the fans.
 * King Sombra: He enslaved an entire empire, used fear on them, presumably killed its previous ruler, and tries to impale Spike, a baby dragon, to get the Crystal Heart, licking his lips as he gets closer to doing so. He ends up being the first major Friendship Is Magic villain to unambiguously die.
 * Mane-iac: Uses her Hairspray Ray Of Doom on the Power Ponies to immobilize them and cages them (with a steady dose of the Hairspray) so she can use her doomsday machine on them. Unfortunately for her, she is foiled when Spike/Humdrum traps some of her minions, distracting her long enough for the Power Ponies to escape and defeat her.
 * Tirek: He either crosses it when he banishes Princesses Celestia, Luna, and Cadance to Tartarus, even though they had already given their powers to Twilight, or when he seals Twilight's friends inside a cage and drains their and Discord's magic, revealing his partnership with Discord to have been a sham.
 * Starlight Glimmer: Crosses it in the two-part season 5 finale, "The Cutie Re-Mark", when she returns to get revenge on Twilight Sparkle by using a time-traveling spell that could change the entire history of Equestria, meaning she'll also keep the Mane 6 from meeting one another and finding out their special talents. However, her actions towards time only lead to several different bad timelines showing what it be like if any previous villain that terrorized Equestrian, including King Sombra, Queen Chrysalis, Nightmare Moon, Lord Tirek, Discord, and even the Flim Flam Brothers, got away with their evil plot, showing Twilight's friends either fighting against the villains or serving them. After several attempts Twilight made to keep Starlight from changing time, Starlight attempted to rip apart the scroll containing the spell, but then she changed her mind after Twilight talked some sense into her about what friendship and cutie marks are truly about, making her see the error of her ways, and then Starlight faced redemption and later became Twilight's student in friendship, as well as apologizing to the ponies she held captive before and even became a close friend to the rest of the Mane 6.
 * Principal Abacus Cinch: She may not be from Equestria or had magic abilities in the human world, but she did try to humiliate Canterlot High so her legacy will endure and make Twilight to join the Friendship Games, or she will deny her from The Independent Study Program, which Twilight really wants to go to. She witnesses Twilight draining Rainbow Dash's magic and learning that she drained a lot of magic. Before the final competition, Principal Cinch and the Shadowbolts trying to convice Twilight in releasing the magic to the point of enforcing her to do it in their villain song "Unleash the Magic". She is responsible for creating Midnight Sparkle, but she just run away.

Naruto

 * Orochimaru: Though he eventually decided against destroying the Leaf Village, Orochimaru begins crosing MEH when his quest to become most powerful and immortal shinobi led him illegally implanted Hashirama Senju's genetic code into 60 kidnapped infants in his attempts for godhood and showed absolutely no concern when they apparently all died (though only one of them turned out survived and became Yamato). In the series proper, he murdered three Chunin hopefuls and stole their faces, sacrificed two of his loyal subordinates to bring Hashirama and Tobirama back as Edo Tensei, killed Hiruzen Sarutobi, the Third Hokage, murdered the Fourth Kazekage after manipulating him and his village into War, and attempted to murder Tsunade, Naruto, Shizune, and Jiraiya after his arms were sealed.
 * Sasuke Uchiha: While deserting his homeland to join Orochimaru in order to become more powerful out of vengeance indeed bad and showed no allegiance to any group from that point (having defected Konoha, Otogakure, and the Akatsuki when he no longer saw any use in them), Sasuke begins crossing MEH when he captured Killer B, the host of the 8-tailed beast, that resulted in the Raikage's vengeful grief, which is only diminished by revelation that Killer B escape but used his capture as a ruse to have fun outside his home village. He dangerously crossed this further when his hatred drove him attacked all kages and killing several samurai because they stood in his way to kill Shimura Danzo, stabbed his most loyal supporter Karin and left her to die, nearly killed his former teammate Sakura and former teacher Kakashi, all of which of led him becoming an international criminal. While in the end Sasuke revealed still have chance of redemption even with horrible things he had done, it's still require Naruto's help to ensure him gone straight as in spite of learning more of the truth about Itachi's crimes from resurrected Kages, Sasuke briefly considered to execute kages instead of save them and declared his revolution against the whole ninja system.
 * In spite of crossing the line, Sasuke's murder on Danzo to avenge his clan ironically saved Konoha and in greater extent, the Five Great Shinobi Village from a worse crisis: Had Danzo left around, he would likely enacted another clan genocide as awful as Uchiha Clan Massacre (in which the target would be Hyuga Clan for allowing one of their Byakugan fell onto hands of Kirigakure and in Ao's possession) and starting a civil war against Tsunade and those who followed her, all of which would doom entire world even before Obito and Akatsuki completed their Eye of the Moon Plan.
 * Deidara: He captured Gaara and helped in extracting his tailed beast from him, resulting in his death. He mocked Naruto with the death of his friend, disrespected Gaara's corpse by using them to make Naruto chase and capture him, and also captured Isobu the Three-Tailed Beast, killing its guards. Even after his death and reanimation, he did not get better.
 * Sasori: He killed the 3rd Kazakage and turned his corpse into a puppet and also tried to kill his grandmother Chiyo as well as Sakura Haruno. Worse, he also killed a large number of people and turned their bodies into puppets as well as claimed that he once used 100 of them to destroy a nation once at the same time, which is proven in a filler episode.
 * Kabuto Yakushi: It is revelated he's Orochimaru's spy and he sacrifaces thousands of people to create his reanimated ninja army to support Obito Uchiha in his war.
 * Danzo Shimura: Tricks Hanzo into thinking that Yahiko is his enemy and later helps the former to kill the latter in exchange for promoting him to become a Hokage, tricks both Nono and Kabuto Yakushi into becoming Konoha's spies and then made them kill each other, stole Shisui's eye, ordered Itachi to kill the entire Uchiha clan, orders Sai and his brother Shin to kill each other, kills the messenger Kosuke so that he cannot tell Naruto about Pain's attack and then gathers his ROOT troops underground without even helping Tsunade defend Konoha hoping he would become Hokage, uses his "6th Hokage" authority to officially declare Sasuke as a wanted criminal, abandons the other four Kages to deal with Sasuke and the Zetsu clones and then mocks Itachi during his fight with Sasuke, and he also took Karin as a hostage to slow Sasuke down, but she meant nothing to him. Though most of his actions supposedly has beneficial consquences by some, these actions are considered despicable due to many casualties and only bring more harm than good.
 * Hidan: He with Kakuzu captured Yugito Nii and helped in extracting her bijuu from her body, resulting in her death. The two of them subsequently slaughtered a temple's worth of monks in order to collect the bounty on the head monk, Chiriku, and he also tortures and kills Asuma Sarutobi then sacrifices his soul to Jashin. He showed no regret in killing Asuma as he physically enjoyed it, and Asuma wasn't his first victim. He even tried to kill Shikamaru & mocked Asuma in front of him. Even when having Shikamaru bury him alive, this did not stop him from mocking the latter.
 * Nagato/Pain: He killed Jiraiya and drowned his corpse, although it can be considered as a self-defence or defence of his own city-state from an invader, but nothing can advocate his attack on the Leaf village and its annihilation and genocide of its populance just to seek out Naruto and his bijuu. He became evil when he ordered Akatsuki members to capture all jinchuuriki and kill them during extraction of their inner demons. He captured Utakata himself in the anime after slaughtering his countrymen ninjas.
 * Madara Uchiha: Having crossed MEH heinous enough to the point of many people despise him, so much that embittered but sympathetic tailed beasts (particularly Kurama) far more redeemable through following deeds:
 * Controlled Kurama to do his dirty work (which also resulted in the loss of what was left on the tailed beast's innocence).
 * Attacked Iwagakuge and badly defeated Ohnoki and Mu to demonstrate his clashing methods in uniting villages with Hashirama's.
 * Manipulated Obito by controlling Kirigakure Shinobi to bring Rin Nohara to her own death in Kakashi's hands so he will do all his dirty work.
 * As resurrected Edo Tensei, defeated the Five Kages easily, thus placing them in a near-death state as soon as breaking himself free from Kabuto's control.
 * Ordered Black Zetsu to control Obito to use the life-risking resurrection technique to him instead of the people who died on the war to finish what he had started.
 * Extracts Kurama from Naruto before stabs Sasuke in the heart and almost killed them both. To add insult to injury, when Naruto and Sasuke gets upper hand, Madara resorted to steal Kakashi's sharingan.
 * Another reason to hate him is Madara somehow successfully keeps himself alive as an undead just as he realized Kabuto undid the summoning dead technique before his soul was brought back to the afterlife, and his long-time evil scheme, even if Obito proceeded his dirty work before his resurrection, proves disastrous and results in many deaths during its process, includes Naruto's parents'. He even went too far by stealing Kakashi's Mangekyou Sharingan just to cross the other dimension and retrieve his Rinnegan from Obito.
 * Obito Uchiha: He decided to follow Madara's plan, caused the death of Naruto's parents and the massive destruction of the Leaf village by extracting Kurama, was involved in the Uchiha Clan Genocide and in doing so being responsible for creating Sasuke's desire for vengeance, killed Nagato's friends, knew about Danzo's actions but kept the truth for himself, and manipulated Kisame, Nagato, and Sasuke to join him and capture the tailed beasts. He also controlled the mind of the 4th Mizukage and the cruel reputation of the Mist Village was thanks to him. Obito was so amoral that realizing the plan of the eternal illusion did not matter to him if anyone will be alive or dead, because in illusion everyone would be alive.
 * Kaguya Otsutsuki: She enslaved the world's people once by putting all in eternal dream and later sucked all vital forces from them, reducing them to mindless husks called Zetsu. Now, after her return, she's doing it again with all friends of all protagonists.
 * Mizuki: Mistreating Naruto like the majority of Konoha villagers may be bad, but he has crossed the line when he manipulated the young jinchuuriki to steal a scroll full of kinjutsu for his own gain. In anime filler, it turns out that he silently mistreated Iruka in the same manner with when he mistreated Naruto, and also, during one of his missions, he brutally murdered his badly injured teammate via suffocation. He crossed MEH once more by starting riots in Konoha Prison. He even tries to kill both Naruto and Iruka, whom he hates psychotically. All of this made him one of the very first challenging advesaries that Naruto ever faced.

One Piece

 * Akainu: Years ago, Akainu destroyed a ship that had many innocent refugees just so that Robin could never get away.
 * Spandam: Ruthlessly attacks a handcuffed Robin simply for speaking out of term. This act even disgusted Rob Lucci.
 * Hody Jones: It was revealed that he was the one that killed Queen Otohime just to place the blame on humans. When Hody was asked what made him despise humans so much, he simply said "Nothing".
 * Higuma: Arguably crosses it when he attempted to drown and kill Luffy even though he was just a child.
 * "Blackbeard" Marshall D. Teach: Kills a former crewmate named Thatch just to obtain his devil fruit. Teach was also the one who captured Ace and killed Whitebeard, harboring no love or respect for his former captain. Teach then stole Whitebeard's devil fruit, the Gura Gura no Mi, by unknown means.
 * Arlong: In a flashback, He killed Nami and Nojiko's adoptive mother, Bell-mère.
 * Donquixote Doflamingo: 10 years ago, he forced Riku Dold III, the former King of Dressrosa, to assault his people by controlling him and his soldier.
 * Captain Kuro: Attacks his own men and attempts to kill them in a powerful attack to eliminate the Straw Hats so that he can complete his plan to live alone in luxury in Syrup Village.
 * Crocodile: Crosses it by planting a bomb that will reduce Alabasta to a crater, activating it when he anticipated that the heroes would find it.
 * Caesar Clown: Oh so many, but in particular givng children a drug that keeps them enslaved to him so that he can perfom experiments on them.

Phineas and Ferb

 * 2nd Dimension Doofenshmirtz: He was in fact a darker (and a more competent) counterpart of the bumbling inventor. Not only has he successfully taken over his Tri-State Area with his army of Norm-Bots, but he also turned 2nd Dimension Perry into a ruthless cyborg programmed to serve him as his general. He even planned to kill the original Perry, Phineas, Ferb, Candace, and even the original Doofenshmirtz while attempting to take over the original Tri-State Area.
 * 2nd Dimension Charlene: She turns out to be a darker counterpart of the bumbling inventor's ex-wife, as she turned several of 2nd Dimension Perry's fellow OWCA agents into ruthless cyborgs (including 2nd Dimension Pinky and 2nd Dimension Peter) during 2nd Doofenshmirtz's reign. She even planned to turn 2nd Candace, 2nd Phineas, and 2nd Ferb into cyborgs after tricking them into freeing her husband from jail.
 * Liam McCracken: He was infamous for hunting down platypi and turning them into trophies ever since he was a kid. He was hired at first by Doofenshmirtz to merely trap Perry, but turns on the deal by trapping Doofenshmirtz as well, planning to turn both the evil scientist and the platypus into trophies. This forces the two foes to work together to stop him.
 * Aloyse von Roddenstein: He crosses it in the 2014 special "Phineas and Ferb Save Summer" when he moved the Earth further away from the Sun to perpetual winter with his latest invention, a revelation that shocks everyone (including Doofenshmirtz, who strongly opposes this). Also, in an attempt to move the Earth further into a new Ice Age that would endanger billions of lives, Rodney disables the reverse switch and the self-destruct button on his machine to ensure that it won't be stopped, which provoked a furious Doofenshmirtz to defeat him.
 * Smile Away Reformatory School Sergeant: He completely and utterly destroys the imagination of Phineas and Ferb through torture and discipline, turning them into mindless drones, though this never actually happened as it was simply a dream Perry was having.

Planet of the Apes

 * General Thade: He mistreated and tormented all the humans around him due to his disgust of their species. He would often overact and even threw a violent tantrums when he learned that Captain Leo Davidson's group stole their horses. Earlier in the movie, he brutally killed two of his own gorilla guards after they had discovered Leo's ship just to keep it a secret. Thade's hatred of humans knew no bounds, even branded Ari with the mark of the human slave when she came to ask for forgiveness.
 * Steven Jacobs: Cared only about profit and little about anyone else's well being. But he truly crossed it when he assisted the police in shooting and killing many of the apes on the Golden Gate Bridge. Despite his death, his damage proved too great: His actions not only drove Koba turned to the dark side, but his involvement with the "ALZ-113" also causes most of mankind's population to die out as he unaware that one of his employees, who took one of the vial, unknowingly realize that ALZ-113 became a deadly virus that kill most human population and transform evolved apes into stronger creatures.
 * Koba: Though Caesar took him in and treated him as a friend, Koba hated humans, so much that it blinded him and caused him to take villainous actions. He killed two guards at the human armory and stole the rifle to kill Caesar and framed the humans. He used this to lounge war on the human city and ruled over the humans and apes with an iron fist, imprisoning those whom too loyal to Caesar and even killed Ash, his young follower for refusing to kill two humans as it would never be what Caesar wanted.

The Powerpuff Girls

 * Dick Hardly: In "Knock it Off", he crossed the MEH when he murdered a perfect Buttercup clone for her Chemical X. And later on, he tried to kill the real Girls for more Chemical X, and forced Professor Utonium watch in horror as they die.
 * Princess Morbucks: In "Twas the Fight Before Christmas", she crosses it when she sneaks into the North Pole and switched the Nice and Naughty Lists in order to allow herself to obtain presents instead of coal (while the children worldwide would receive coal). This (among her other actions) forced Santa Claus to place her on the Permanent Naughty List.

The Simpsons

 * Mr. Burns: In "Curse of the Flying Hellfish", he threatens to shoot Bart and then tries to drown him.
 * Sideshow Bob: In "Funeral for a Fiend", he tricks everyone in Springfield into turning against Bart by convincing them that Bart lead him to insanity. He then fakes his death, pinpoints it on Bart, and everyone sees Bob die as a legend. However, he finally crossed it when he had his brother lead Bart to the funeral home to be cremated alive.
 * Russ Cargill: Although at first he only wants to prevent Springfield's pollution from spreading, he crosses the line by attempting to destroy Springfield (killing its entire population) with a time bomb.
 * Cecil Terwilliger: Attempts to kill his brother Sideshow Bob, Bart and Lisa, and blow up the Springfield dam and flood Springfield, to frame Bob and make off with the money he embezzled.
 * Lyle Lanley: After setting up his faulty monorails, he left many Springfield citizens to die on the monorail. He had also done so in the past.
 * Jessica Lovejoy: She steals the money of the church and then blames Bart for it.

South Park

 * Eric Cartman: Having Scott Tenorman's parents killed and feeding them to him as chili. This was the most prominent indication of his progression from a bratty, selfish jerk to a truly evil character since the start of the series.
 * Even worse, as The Coon, he tamed Cthulhu to destroy everything and everybody for his own personal amusement.
 * SkankHunt42: The worst Internet troll, he harasses all women and girls in internet with no reason. He made Freja Ollegard commit suicide. The girls started breaking up with their boyfriends.
 * Sheila Broflovski: In Bigger, Longer, and Uncut, she shoots Terrance and Phillip in the head even after her son, Kyle, pointed out to her that starting a war against Canada and killing Terrence and Phillip was wrong and pointless.
 * Mr. Herbert Garrison: He tried to stop the gay marriage bill from being passed to the degree that he almost had Stan and Kyle killed, and also threatened to break Cartman's legs and burn his house down if he didn't take his forged egg.
 * Ultimately becomes a Complete Monster after he levels Toronto with a nuclear bomb in "Super Hard PCness".
 * Stephen and Linda Stotch: Linda crosses it when she tries to kill Butters by releasing the brakes on her car which causes it to roll into the ocean. Stephen & Linda both cross it when they beat Butters so hard that it could never be shown on screen after Cartman frames Butters for trash-talking his parents. They then go downhill from there by selling him to Paris Hilton to locking him up in a basement and trying to feed him a woman they killed. Not only that, the attempt to 'ground' him for everything and anything, and Butters is so scared of his father he imagines him as a monster.
 * Grandma Stotch: She beat up and constantly bullied Butters to the point of him having a nervous breakdown for no reason.
 * The Citizens of South Park: Constant pestering Britney Spears until she tries to commit suicide, and when it fails they continually do it while mocking her appearance. Ultimately, THEY kill her instead of her killing herself, so they could get a 'fresh harvest' of corn in the fall

Spongebob SquarePants

 * Plankton: While in series he was a comedy villain, in the first movie he shows a much darker and psychotic side when he steals King Neptune's crown, frames Mr. Krabs for it, enslaves Bikini Bottom, sends a bounty hunter named Dennis to kill SpongeBob and Patrick and shows excitement and joy when Mr. Krabs is going to be killed. In process, he has became a dangerous threat (as he also brainwashed King Neptune along with all the Bikini Bottomites via mind-controlling helmet at climax) against not only the Krusty Krab, but Bikini Bottom itself.
 * Burger-Beard: Though being comedic, Burger-Beard crosses this by stealing the Krabby Patty recipe through a magic book's powers, inevitably turning the entire Bikini Bottom into a post apocalypse state as the majority of Bikini Bottom citizens are unable to cope without Krabby Patties. He outclassed Plankton as the most dangerous and formidable antagonist in the franchise.
 * Mr. Krabs: The episode One Coarse Meal has been debated as perhaps the darkest episode in the SpongeBob SquarePants series due to Krabs' actions. Upon discovering Plankton's phobia of whales, he dresses up as Pearl and terrorizes Plankton for 17 days, giving him nightmares and eventually leading him to attempt suicide. Spongebob offers to help Plankton by revealing Mr. Krabs's fear of mimes, one whom Plankton hires to terrorize Mr. Krabs in turn. Other than that, Mr. Krabs gets no proper comeuppance for attempting to drive Plankton to suicide (i.e. arrested), as he only had Plankton's hired mime agitate him.
 * Another irredeemable action occurs in "Jellyfish Hunter", where he kills jellyfish in a factory just to get the jelly from them for the customers, and get more money (after his defeat, he reluctantly took jelly off the menu).
 * He also made lies in the newspaper, the Krabby Kronicle, which ruined the Bikini Bottom citizens' lives (and because Plankton lost his restaurant thanks to Krabs, he mentioned "And I thought I was evil") and even counterfeited a massive amount of money in the end (though it was doubtful that he would spend any of it), which is extremely illegal.
 * In "The Cent of Money", he uses Gary as a coin magnet to steal coins from everyone and not caring for the snail's suffering (he even calls Gary a "sneagle" rather than a snail).
 * Finally, in "Out of the Picture," he tries to kill Squidward because his artwork would be more valuable if he was deceased. This also confirmed that his money-grubbing behavior has drove him alarmingly insane.
 * Mrs. Puff: After years of putting up with SpongeBob's reckless driving, she was finally driven insane in "Demolition Doofus", when she apparently lost her ability to puff following the latest failed driving test. She later gets SpongeBob into a Demolition Derby in hopes of him getting killed by offering him "extra credit". As his bad driving makes him a star, Mrs. Puff snaps and tries to run over SpongeBob by using a huge monster truck. Instead, she destroys her boating school, but she turned back to normal and regained her sanity to her disappointment.

Star Wars

 * Kylo Ren: Burned down an entire village and killed innocent people, which caused the horrified Finn to defect the First Order to join forces with the Resistance. Even though he had a tragic past, Kylo Ren crossed the MEH once more when he murdered Han Solo, his own father, in cold blood. However, in a surprising twist in MEH crossings, he betrays and murders Supreme Leader Snoke, taking command of the First Order, because he wants "let the past die".
 * Emperor Palpatine: Palpatine was evil, dishonest, psychopathic megalomaniac to the core whom actually having a very large records of crossing MEH over the course of his life until his downfall, but the most famous of these acts are:
 * Starts the Clone Wars to extend his cadency of Supreme Chancellor.
 * Turns Anakin Skywalker to the dark side by taking advantage of his loved ones due to his massive power over the force.
 * Gives the clone troopers Order 66, leading to the Second Great Jedi Purge.
 * Tries to kill Luke Skywalker with Force lightning, which turned out to be a fatal mistake in his life as by torturing Luke, he unknowingly aided Luke to redeem Darth Vader who unexpectedly rushed to single-handedly toss him into Death Star core that results in his demise.
 * Darth Maul: In the TV series, he manipulated both Death Watch and Black Sun and turned them into his private army to conquer planet Mandalore, he also put his puppet ruler in charge and killed Duchess Satine, Obi-Wan Kenobi's old love much to his sorrow while he smiled gleefully. In the movie, it's likely when he kills Qui-Gon Jinn|Qui-Gon and tried to do the same on Obi-Wan where unfortunately, this led the Jedi to slice his torso in retaliation of his murder. Another evil act is blinding Kanan Jarrus on Malachor.
 * Count Dooku: He created a separatist alliance against the Republic, he betrayed, wounded, murdered, lied and manipulated to get advantage. He killed Jedi Master Syfo Dias and took his identity, recruited Jango Fett as a source of clone army for his war, but he lost that. He betrayed the Republic to Darth Sidious, sent Obi-Wan, Padmé Amidala and Anakin to execution arena, cut off Anakin's arm, led a war against the Republic, during the Clone Wars he sponsored horrific experiments, inventions of weapons of mass destruction and destructive starships. He ordered to kill all witnesses and to terminate Assajj Ventress, when his master suspected him plotting against him. He later abandoned her, when he saw no more use of her and he ordered General Grievous to kidnap Chancellor Palpatine when he led a massive ambush on Coruscant.
 * Grand Moff Tarkin: As one of the most infamous crossings of all time, he destroyed the planet Alderaan after making a false promise to Princess Leia that he would spare Alderaan if she revealed the location of the rebel base. Hoping to spare both, she lied and claimed the rebels were on Dantooine. Tarkin however decided to destroy Aderaan anyway, to frighten planets away from rebelling. He also planned to continue Emperor Palpatine's Empire after he was gone.
 * General Hux: In much more extreme way than Grand Moff Tarkin's actions, he ordered the Starkiller Base to destroy the Hosnian System, which not only destroyed the planet, Hosnian Prime (the capital planet of the New Republic), but also killed billions of living beings, destroyed the Galactic Senate and much of the New Republic Starfleet.
 * Jabba the Hutt: Jabba crosses the Moral Event Horizon when he orders Luke, Han, and Chewbacca to be thrown into the Great Pit of Carkoon to be eaten by the Sarlacc, after Luke slaughtered his pet Rancor, despite the fact that, in this situation, Han and Chewbacca were relatively innocent, whereas Luke angered Jabba (though unintentionally; he was defending himself against the Rancor and did not wish to kill it, but saw no other choice).
 * Darth Vader: As Anakin Skywalker, he killed an entire village of Tuskan Raiders to avenge his mother's death. He also cut off Mace Windu's right hand, helping Palpatine to kill him. He then became Palpatine's Sith pupil (Darth Vader), for his order he massacred children in the Jedi temple, choked his beloved Padme after wrongly thinking that she betrayed him. For 20 years he preserved totalitarianism of the Galactic Empire, took over Cloud City, froze Han Solo and gave him to Boba Fett, cut off Luke Skywalker's right hand, and he, along with the Emperor, played on Luke's emotions after capturing him.
 * By Return of the Jedi, Vader is shown to be subverting the crossing, as only Luke Skywalker believes that Vader still has a chance at redemption. Indeed, he proves his worth by saving his son (Luke) from the Emperor's shocks. Vader tosses the Emperor down the Death Star, killing him, but the shock power killed Vader as well.
 * Pong Krell: Krell crossed the MEH many times over, being stern and strict about Rex and the clones obeying his reckless orders that purposely led many of the clones in battle to their deaths with his strategies, ordered clone troopers Fives and Jesse to be executed for their defiance, he then tricks his men into killing each other and always sadistically gleeful whenever he killed a clone trooper when they turned on him after his treachery was revealed and taunted Captain Rex into shooting him, knowing that he could never bring himself to do it.
 * Barriss Offee: Arranged the Bombing of the Jedi Temple (which occurred in the Temple's hangar), killing six Jedi and several Jedi Temple Workers. She also framed her (former) friend Ahsoka Tano for the crime along with killing a key suspect in the bombing, which resulted in Ahsoka leaving (after being exonerated) from the Jedi order.
 * General Kalani: Killed millions of innocent people who were against oppression separatists in Onderon causing a massacre of civilians in mass of women, men, elderly and even children,and even after such atrocities against an entire planet, Kalani still alive waging war against the Galactic Republic at the outer edge, invading neutral planets or enslaving planets or races and allied Galactic Republic.
 * Savage Opress: He killed his brother, who helped him becoming Asajj Ventress' pupil as his final test. He committed numerous genocides for order of Count Dooku, he killed king of Toydaria despite Count Dooku had earlier commanded him to capture him alive. He used intimidations and death threats to find Darth Maul and save him. He helped him in building an army from gangsters to conquer planet Mandalore, which ended with a success.
 * Durge: He caused numerous mass murders under no orders, for no reason other than it was fun.
 * General Grievous: During his military campaigns, ambushing the Jedi party on Hypori and killing nearly everyone there, killed thousands of Jedi and never showed any emotion or remorse for his evil deeds of rampage and murder of millions.

Transformers Film Series

 * Megatron: He, along with his master The Fallen, was the cause of Cybertron's destruction when Decepticons and Autobots have started a war that has destroyed much of Cybertron. These practically give a logical reason why Optimus Prime lost his sympathize towards him as his "brother", as he avenges this MEH crossing deed by either damaging his face with his own cannon in Revenge of the Fallen or de-spining him in Dark of the Moon.
 * In first movie, he killed Autobot Jazz by ripping him in half and almost Sam plunging towards his death.
 * After being resurrected in Revenge of the Fallen, he attempts to painfully rip Sam's skull open to read his thoughts, but is stopped by Optimus. Megatron then cowardly and brutally murders Optimus when his back is turned.
 * In the Dark of the Moon prequel comic Rising Storm, Megatron has Shockwave reorganize the Decepticon Empire, which resulted in the deaths of Astrotrain, Fearswoop, Skystalker, Divebomb, Deadlift, Brimstone, Sonar, Storm Surge, and Blademaster (and possibly Ravage, Rumble, Beastbox, Ratbat, Buzzsaw, and Bludegon) and the near-deaths of Soundwave, Barricade, and even Shockwave himself.
 * In the Dark of the Moon videogame, he attempted to drain Starscream's spark as punishment for bring a piece of MechTech containing a homing beacon, but was interrupted by an alert from Soundwave that they were under attack. He also brown down the Autobot Warpath.
 * Despite the loss of many Decepticons and having to use Starscream as bait, those is done to prepare for the return of Sentinel Prime in the Dark of the Moon film, where it is revealed that Megatron blackmailed the Prime into defecting the Autobots. However, this deed ultimately backfires as Sentinel manipulated him all along so he can usurp his leadership over Decepticons, as revealed by Carly who convinces him to attack Sentinel out of rage later. He also destroyed the monument of Abraham Lincoln to take the throne.
 * When he returns as Galvatron in Age of Extinction, he controls all of the KSI man-made transformers after manipulates KSI via knowledge of transformers physiology in his mind, making them a new Deception army, and attacks Hong Kong in order to takes back the "seed" and destroys the whole city.
 * In The Last Knight, he becomes involved in Quintessa's scheme to kill Earth/Unicron by using a magical staff hidden on the planet by the Guardian Knights. He also killed Sir Edmund Burton with his fusion cannon and betrayed the Transformer Reaction Force.
 * Barricade: Tormented Sam to gain the location of his great-great-grandfather's glasses in the first film. In Dark of the Moon, he assisted a Protoform soldier in killing Que/Wheeljack under Soundwave's orders. In The Last Knight, he suggests to Megatron that using the Transformers Reaction Force will lead them to Quintessa's staff. The most frustrating part about him is that his MEH crossings are unable to be avenged because he is unable to stay dead.
 * Starscream: He crippled Ironhide and Ratchet and killed many human soldiers in the first film. He blew up the Autobot starship Xantium in Dark of the Moon under Dylan's orders and took down some NEST Ospreys, and the novel adaptation also had him killing Dino/Mirage.
 * Soundwave: In Revenge of the Fallen, he hacked human government databases to steal top secrets and ordered Ravage to steal the Allspark shard to revive Megatron. In the Nefarious comic sequel, he murders the young Autobot Breakaway, sends his animal minions on Bumblebee, Jolt, Knockout, and Dune Runner, and ultimately steals the plans for a replica All-Spark after helping them take down Carter Newell. In Dark of the Moon, he ordered Laserbeak to kill anyone affiliated with the Moon Landing Project (which possibly included one member's family), threatened to torture Carly, sent Barricade and a Protoform soldier to kill Que/Wheeljack. In an unused draft which is still seen in the comic and junior novel adaptations, he personally kills Dino/Mirage and uses his corpse to taunt the captured Autobots. His crossing of MEH are all avenged when Bumblebee kills him.
 * The Fallen: He betrayed his brother Primes out of pure spite toward humans by tring to gather Energon from Earth's sun, which could have annihilated the planet in the past. He tries to resume his plans once more after Megatron had assassinated Optimus, but ultimately killed by a revived Optimus himself.
 * In early drafts seen in the comic and novel adaptations, The Fallen promised Megatron the powers of a Prime, something that Optimus would later expose as a lie. This would lead to him betraying him and leaving him to die. The video game adaptation additionally depicts The Fallen battling Megatron.
 * Bludgeon: In "Culture Shock", a Titan Magazine comic set after Revenge of the Fallen, Bludgeon went on a rampage in Las Vegas, weakening and taunting the young Autobot Jolt in the process. He tried to fire his tank mode at some hapless gamblers only for Jolt to take the shots. He nearly tried to kill Jolt, yet the Autobot was able to electrocute him to defeat. However, it is later revealed in "Inside Out!" that he purposefully allowed himself to be captured by NEST so that he could spark a jailbreak and form a splinter faction of Decepticons. Once this was accomplished thanks to Scalpel, Bludgeon murdered fellow Decepticon Brakedown to encourage discipline amongst the other 'Cons (Skywarp, Tankor, Lockdown, Dead End, Thrust, and Reverb) before leading a vicious attack on the few helpless Autobot guards: Brawn, Smokescreen, and Wideload. He was stopped short of murdering Brawn by the arrival of Bumblebee, Springer, and Gears, but Optimus allowed him and his new army to leave to prevent civilian casualties. After Bumblebee, Hubcap, and Slap Dash neutralized Crankstart, Brimstone, and Trenchmouth in Utah, Bludgeon declared open war on the Autobots with a scheme to tear down NEST before coming for them ("Shadow War"). Surprisingly, he formulates an all-out assault once Wheelie turns traitor and informs him of his enemies' arrival. Sending Lockdown, Dead End, and Tankor to surprise the Autobots, Skywarp and Thrust proceed to box them in with strikes from above and shoot Springer out of the sky. Revealing that they have been betrayed, Bludgeon personally murders Slap Dash with his sword and weakens Hubcap with energy shurikens ("Divided Loyalties"). However, he is suddenly beaten by Megatron, who was unimpressed with Bludgeon's insubordination yet spared him in case he was useful ("A Short, Sharp Lesson"). In the Unite for the Universe comic, Bludgeon is tasked by Megatron to acquire the Project Unite technology in exchange for control over the Decepticons on Earth. However, the mission went sour because Starscream tipped off the Autobots, wanting the power of Project Unit for himself. While Autobots and Starscream's Decepticons clashed, Bludgeon attempted to extract revenge on Starscream, only to be overpowered by Starscream and taken into NEST custody. In the Rising Storm comics, Bludgeon is shown killing Storm Surge, mistaking him for Mirage. Nevertheless, all of Bludegon's MEH crossings are avenged once he is taken out by a gunshot wound to the chest near the end of Rising Storm.
 * Carter Newell: Following the death of his parents at the hands of the ancient Seeker Fortress, Newell began plotting the seeds for the extinction of all Cybertronian life using a replica of the destroyed All-Spark, yet was ultimately undone by Optimus Prime and was slain by Buzzsaw. Fortress sought to right all be unknowingly caused by taking the unstable replica All-Spark away from Earth. Newell also killed both Kirkpatrick and Reedman, and brainwashed Ravage, Ransack, Armorhide, Blazemaster, Tankor, Skystalker, Brawn, Smokescreen, Sonar, and Thrust, and some unknown bots that are possibly Lockdown and Divebomb.
 * Skywarp: Skywarp was in charge of the attempted resurrection of Devastator, only to be undone by the Autobot Stratosphere in the Titan Magazine comic "Head in the Clouds". He later tried to recruit the impulsive Blazemaster to Bludgeon's army in "Turn and Burn", claiming that the Autobot has what is takes to become a Decepticon. In "Divided Loyalties", he assists Thrust in boxing in the Autobots and taking down Springer.
 * Dead End: Tore off Jolt and Dune Runner's arms, reduced Wheelie to shreds, and injured Bumblebee during Christmas. These crossings are avenged when he was taken down by the yellow Autobot.
 * Crankstart, Brimstone, and Trenchmouth: When the Autobots were becoming hated due to Bludgeon's machinations, the trio went on a rampage through Salt Lake City, though this MEH is avenged once they are neutralized by the Autobots Bumblebee, Hubcap, and Slap Dash.
 * Sentinel Prime: He betrayed the Autobots to the Deceptions, executed Ironhide and many NEST soldiers, and tried to ruin Earth and enslave human race. Worse, it turned out that he manipulate Megatron all along as he proceed to usurped the Decepticon leadership so he can have Decepticon army all by himself. On top of that, damage that he caused was too great; human government lost their faith with the Autobot, and Harold Attinger uses it as propaganda against Cybertronians on earth further.
 * In early drafts of Dark of the Moon seen in the comic and novel adaptations, Sentinel tried to kill Bumblebee after killing Ironhide, only for Skids to take the shot. He also killed Mudflap and would have done the same to Optimus at the Lincoln Memorial, though he spared him instead to save the spacebridge pillars when they came under attack.
 * Dylan Gould: Betrayed humankind to the Decepticons and worked as their spy, ordered his bodyguards to beat Sam and had Starcream shoot the Autobot's ship. He also personally blackmailed, mocked and attempted to kill him. Other reasons to hate him was when Dylan reveal his true color, he has already became one of high-ranking Decepticon command and receiving disappointing comeuppance (electrocuted by one of Sentinel's pillar).
 * Shockwave: According to the Rising Storm comics and the Dark of the Moon video game, Shockwave is a powerful assassin. On Cybertron, he murdered Elita-1's sister Chromia. When revived on Earth by Megatron, Shockwave kills the All-Spark Mutation-turned-Autobots Longarm and Salvage and several humans near Dalian, China. He also instructs Astrotrain to work on a project involving his pet Driller and a Brain Unit, instructing him to terminate the latter once he has exceeded his usefulness. Anticipating the drone's gaining-of-sentience (during which he remains himself "Brains") while observing Autobots capture Fearswoop after killing Skystalker and Divebomb, he instructs Starscream and his men to retrieve the drone, killing Deadlift once he attempted to defend his master. Starscream's forces converge on Brains only to encounter Bumblebee, Wheeljack, Mirage, and even the diminutive turncoat Wheelie in Philadelphia. With the NEST base in Diego Garcia undermanned, Shockwave proceeds to kill Knockout, Dune Runner, and the mentally-impaired Autobots (Armorhide, Blazemaster, Smokescreen, and Brawn) before turning towards the trembling humans left to fend for themselves. When Shockwave asked who was in command, Theodore Galloway told him that he was. However, Shockwave killed Galloway and the other humans save one and asked his question one more time. After making short work of Jolt and freeing Fearswoop, he made his way to Philadelphia, where he killed Elita-1 (fresh from her battle with Astrotrain) and critically injured Wheeljack and Mirage. He was about to be plummeted to death by Optimus Prime only to be rescued by his Driller. In the Dark of the Moon film, Shockwave siccs his Driller on Sam, Carly, Epps, and other humans and knocks Optimus out of the sky once his pet is killed. All of his EMH crossings are avenged once Optimus kills him, though this would later result in Nitro Zeus making his way to Earth to avenge him.
 * Lockdown (Transformers Film Series): Starts by ripping the spark out of the gravely injured Ratchet, killing him. Later Lockdown destroys the Yeager family home during the Cemetery Wind chase scene in Texas and kills Cade's friend Lucas by throwing a grenade and turning the man into a statue of Transformium. He also tries to recapture Optimus by using a giant magnet from his ship by absorbing metallic objects then dropping them on the Autobots in Hong Kong endangering many civilians in the process. The Titan Magazine comics also show that Lockdown, an ex-Decepticon, murdered Knucklehead once Megatron died in Chicago, and temporarily took command of the Decepticons that survived that battle only to be hunted by the Autobots. He also claims that he was sent by techno-organic aliens dubbed "The Creators", though Quintessa would later claim herself to be the one who sent Lockdown after Optimus in the first place.
 * Harold Attinger: Uses the casualties of Chicago as propaganda against Cybertronians on Earth further, allowing no one to against him when he had Ratchet, Sideswipe, Leadfoot, and many other Autobots (possibly including Dino/Mirage and Roadbuster, given that Wheelie and Topspin are later shown to be alive in The Last Knight) hunted down and killed, and purging other humans for choosing Transformers over humanity, until his nefarious actions are ultimately put into an end at hands of Optimus Prime and Cade Yeager alongside the latter's family and Autobots Bumblebee, Hound, Drift, and Crosshairs. Other reasons to hate him are that he had manipulated both the Autobot Brains and his pawn Joshua Joyce to creates mass produced artificial Transformers using the corpses of the Decepticons as well as some of the Autobots he had killed as ruse to gain a Seed for himself as he had secretly had a deal with Lockdown to do so. His deed ultimately become his undoing when he uses Megatron's remains to create Galvatron, who not only revived Megatron but also evolved into a stronger Transformer that proceeded to take control of Stinger, Junkheap, and all the other artificial Transformers, turning them into Decepticons. Fortunately, most of his actions are avenged when Optimus shoots him down, but this is not enough to clear the Autobots' names until Cade reveals to Santos and the Transformers Reaction Force that the real reason humanity turned on the Autobots was because they merely gave up on them.
 * Joshua Joyce's betrayal as soon as he aware with Attinger's dark nature also revealed that this whole record of MEHs would threaten to ruined both KSI and Joyce's good name and turned them all into war criminals. All of these are something that Joyce greatly despised, as in fact, Joyce actually wants to made the world into the better place, not induce the chaos toward it instead like what Attinger actually done in spite of his intentions.
 * James Savoy: Was first shown leading an attack on Ratchet and stated that his sister was among the humans killed in Chicago, justifying his reason for joining Cemetery Wind. Has already a step ahead by threatens Tessa in order to force Optimus Prime out of hiding. Later he tries to brutally kill Cade Yeager and his family in Hong Kong. Worse, in his last attempt to take their lives, he was completely indifferent with Cade whom tell him that he understand the pain that he has, and Cade was ultimately forced to let James fall to his death.
 * Quintessa: Claiming herself to be the creator of the Transformers race, she brainwashed Optimus into helping her reclaim her staff, which had been "stolen" by the Guardian Knights once they betrayed her, though they claim that Quintessa is a liar. The staff was the key to her plan of killing Earth/Unicron in an effort to revitalize Cybertron/Primus. Though this went unmentioned in the film proper, she also tasked Megatron/Galvatron with finding the staff and was possibly responsible for reformatting him into a new body.
 * Dreadbot: Prior to being captured by the Transformers Reaction Force, Dreadbot broke into a human bank and killed nine humans, surprisingly all without taking any money. This MEH crossing is avenge once Dreadbot is eaten by Grimlock.
 * Berserker: Berserker is considered to be the most homicidal Decepticon in the entire live-action continuity family, going as far as to suck human blood/brains (depending on how his one line of dialogue in The Last Knight is heard). Because of this, he is left in TRF custody.

Yu-Gi-Oh!

 * Yami Marik: He caused Marik's turn into villainy. During Battle City Finals, Yami Marik crosses it when he gleefully traps Mai Kujaku in her own mind after having assaulted her psyche during their duel. He later tries to kill Odion, but not after he defeated Yami Bakura and trapped Ryo Bakura's body (without noticing the Spirit in the Millenium Ring had escaped) into the Shadow Realms.
 * Dartz: Near the end of the fourth season it's revealed that he was responsible for the death of Rafael's family (in the dub, the family survived the cruise ship attack but has completely forgotten him) as well as ruining the rest of his henchmen's lives to convince them to join his crusade. This also includes framing the Kaiba family (Kaiba Gozaburo and Seto along with possibly Mokuba) for funding a war that ruined a town and caused Alister's family to get killed (in the dub, his family members were captured instead). He paid a gang to burn a church that killed Valon's caretaker (a nun), which caused Valon to attack the gang responsible and get locked up (in the dub, Dartz simply framed Valon for his first crime at age 9).
 * Mr. Ishtar: He ritualistically carved up his son's back, which led to the birth of Yami Marik, and later tortured Odion.
 * Yami Bakura: He crosses it by possessing Ryo Bakura, trapping Yugi's friends' souls, and forcing Yugi to a Shadow RPG Game.
 * Weevil Underwood: He rips up a card that he claimed contained Yugi's soul, which would have killed him, yet he then revealed that he was only kidding as the card was a common Insect type card.
 * Zorc Necrophades: He crosses it when sacrificing his pawn, Thief King Bakura, in order to revive himself. He also destroys as many of Atem's minions as possible. Besides, Zorc is even worse in the anime than his original counterpart in the manga. In the anime, he and Yami Bakura are entirely one and the same, making him the mastermind of Yami Bakura's heinous actions.

Disney and Pixar films

 * Ernesto de la Cruz: Driven mad by greed and jealousy, he poisoned his own bandmate and stole his songs, which was the real reason why Héctor never made it home after leaving his family and led to the Rivera Family forbidding music. Later, he crossed the line when he "extended" Miguel's stay and deliberately threw him over the side of a building without a shred of empathy.
 * Dawn Bellwether: Driven by racial and political hatred, she darts predators with a serum made from the juice of Night Howlers, making them go savage and throwing Zootopia into chaos without being noticed, going so far as to leave many animals prejudiced or even injured. She even crosses the line when she nearly kills Judy Hopps by attempting to poison Nick with the serum before she is fooled.
 * Jafar: Crosses it when he lies to Princess Jasmine about Aladdin being executed.
 * Ursula: She lured merpeople to their doom and imprisoned them in her lair, but she crosses the line when she sabotages her bargain with Ariel and attempts to trick Prince Eric into marrying her, taking King Triton's trident and crown and turning him to a polyp when her plan succeeds.
 * Gaston: In the final battle with the Beast, after the Beast spares his life, Gaston rewards him by literally stabbing him in the back.
 * Paolo Valisari: Pretends to be in love with Lizzie McGuire, but was in fact manipulating her to pose as his look alike ex-girlfriend/singing partner Isabella to frame Isabella for lip-syncing and humiliate Lizzie in the International Music Video Awards.
 * Lyle Tiberius Rourke: Planned to steal the Heart of Atlantis all along without telling Milo and punched the King of Atlantis, mortally wounding him given how old he is. It was enough for Dr. Sweet to turn against Rourke and try to unsuccessfully treat the King's wounds. He also punched Milo down for his "soapbox", and stepped on the picture of Milo and his late grandfather, breaking the glass of the frame.
 * Prince Hans: He manipulates the naive Princess Anna by getting her to fall for him and rule her kingdom. When Anna was revealed to be slowly freezing to death, Hans betrays her and leaves her to her doom. Later, he uses her alleged death as an excuse to charge Queen Elsa with treason and attempts to carry out her execution himself.
 * Governor Ratcliffe: In the end of the first film, he crosses it when he tries to shoot at Chief Powhatan, but Smith takes the bullet, but survives as it is not fatal. Thomas and his gang are appalled by this and discover him for the liar he was. In the sequel, he allows Smith to fall to his "death" and tells the King that he has died but after he finds out he was still alive, he hires a circus performer to bear bait in front of Pocahontas and the king's court to make Pocahontas act savage and be punished by the king to get her out of the way so he can declare war on the Powhatan tribe with his fleet.
 * Syndrome: Though given a sympathetic backstory by being firmly rejected by Mr. Incredible when he wanted to be his sidekick, he crossed the line when he shot a missile at Mr. Incredible's family twice, believing that he would get over it as he told him that he worked alone. He and Mirage also killed several superheroes in the past so he could pretend to be a superhero and eventually sell his own inventions so that nobody would actually be super.
 * Ramsley: Poisons Elizabeth Henshaw and lies to Master Edward Gracey by claiming she committed suicide which caused him into killing himself. This was responsible for the curse of the Gracey Manor (also known as the Haunted Mansion).
 * Percival C. McLeach: Tries to feed Cody to a swarm of crocodiles when he had outlived his usefulness.
 * Scar: Killed his brother, Mufasa, to become king of the Pridelands by shoving him over a cliff to his death.
 * Zira: Menacingly threatened Kiara, abused her own son, threatened to kill an entire pride, ambushed Simba and greviosuly wounded him, later attacked Kovu, then threatened to kill her own daughter before trying to attack Simba once more.
 * Judge Claude Frollo: Killed Quasimodo's mother and tried to drown him simply because he was deformed.
 * In Kingdom Hearts: Dream Drop Distance, he crosses it when he plans to use the Wargoyle Dream Eater to pass "righteous judgement" on all the gypsies. Even Riku explained "Once you've fallen that far, there's almost no coming back".
 * Shan-Yu: Had one of his men kill one of the two messengers, obliterates an entire village, and (presumably) kills an innocent girl who lost her doll.
 * Lots-O' Huggin' Bear: Abandons Woody and his friends to die in the incinerator after they save him by not pressing the emergency stop button, yelling "Where's you kid now, Sheriff?". This has been a particularly notable example that was acknowledged by numerous audiences when first seeing the film theatrically, particularly because Lotso did have a tragic backstory, but denied the perfect opportunity to redeem himself.
 * Professor Ratigan: He crosses the MEH when he feeds one of his henchmen to his cat Felicia, almost does the same to the Mouse Queen, and almost kills Olivia by throwing her onto the cogwheels of Big Ben. It is also stated (and often debated) that in his song, he drowned widows and orphans.
 * Prince John: Ordered Friar Tuck to be hanged, knowing that in doing so he would lure out Robin Hood. Sir Hiss was shocked that he would do such a thing.
 * Cecil Clayton: Crosses it when he shoots Kerchak, mortally wounding him. He also tries to kill Tarzan, even after he spares his life. This is similar to Gaston's behavior and much like Gaston, this leads to his death.
 * Cutler Beckett: Hanged anyone associated with pirates, including a young boy, and later killed Governor Weatherby Swann simply for finding out that he who stabs Davy Jones must take his place as the Flying Dutchman's captain.
 * Randall Boggs and Henry J. Waternoose III: Planned to kidnap as many children as possible and (possibly) kill them just to keep a company going and to preserve power for the monsters.
 * Turbo/King Candy: He left his game titled TurboTime and tried to take over the newer videogame RoadBlasters out of pure envy, and he later invaded Sugar Rush and turned Vanellope von Schweetz into a glitch while trying to delete her code, becoming its ruler. Later in the film, he convinced Ralph that if Vanellope raced, they would shut down the game and she would die with it. This in turn caused him to destroy her cart and nearly ruin their friendship. He tries to kill Vanellope after the latter was about to win the race, only to have his true identity revealed via her glitching power and ended up devoured by a Cy-Bug in his failed attempt to stop her. As a Cy-Bug, he stopped Ralph from killing all of the other Cy-Bugs who plans on using Diet Cola Mountain as a Beacon and forced him to watch Vanellope die at the hands of the Cy-Bugs.
 * Tex Richman: In order to shut down the Muppet Theater, Tex uses an ax to cut down the power and uses his car to cut off the telephone wires by backing it up towards the phone tower, thus ruining the Muppet Telethon.
 * Amos Slade: Comes dangerously close to crossing it when he is about to shoot Tod even after he saved his and Copper's lives, but manages to avoid it when Copper convinces him to stand down and let Tod live.
 * Giant Magnet: Although originally designed to destroy, he constantly tried to send the appliances on the conveyor belt, which leads to the crusher. Later, he placed their "master" on to the belt.
 * Chick Hicks: Deliberately sideswiped King just to win the Piston Cup. The crowd turned on him and booed him for this.
 * Judge Doom: Plotted the genocide of his own Toon species with Dip. In the past, he was responsible for killing Eddie's brother by dropping a piano on him. One of his most horrible acts was dunking a cartoon shoe in a vat of dip with sadistic glee.
 * The Coachman: Crosses the MEH when he ran a place known as Pleasure Island that turned little boys into donkeys and then sold them to slavery. When Lampwick turned into a donkey, it was considered to be one of the scariest moments in cartoon history.
 * Miles Axlerod: Though his identity has not yet been revealed at this time, he orders that McQueen be killed for saying that he'll continue to use Allinol in the next race. Double-bill as Professor Z is the one who is given the order and is more than willing to carry it out. If not, they cross it when they rig Mater with a bomb and intend to blow him and McQueen up when he gets too close.
 * King Stefan (Disney's Maleficent): Despite the fact that he was remorseful for stealing Maleficent's wings and he once befriended her (as well as introducing her to true love's kiss), Stefan eventually hated Maleficent once she retaliated by cursing Aurora, so much to the point that he was driven to the dark side farther than Maleficent herself was. He left his dying queen to perish for the sake of his obsession with hunting Maleficent, sent his men to hunt the fairy down (only to return with failure and severe injuries), and then tried to stab her from behind when Maleficent spared him. Another reason to hate him was he HIMSELF was responsible for kicking her to the dark side in the first place by stealing her wings.
 * Bradley Uppercrust III: Attempted to injure his opponents in the X-Game finals (in methods which could have severely injured or even killed them). He even callously leaves his right hand man Tank to die in the burning X-Games fabric logo. Max and Goofy rescue Tank and Max beats Brad to the finish line. Tank then turns on Brad for betraying him and slingshots him into the X-Games Blimp.
 * Mor'du: Crosses the MEH when, as revealed in The Legend of Mor'du, he throws his kingdom into war and chaos by shattering the bonds of his family and demanding a spell from the witch that would give him the power to conquer his homeland. He drinks the potion in front of his brothers, and instead of healing the family bonds he has broken, he accepts the form of the giant bear he has been turned into and slaughters them and his kingdom's civilians in cold blood. In the movie, he attacks the highland clans and makes attempts to kill Merida until Queen Elinor comes to the heroine's rescue. As it's implied, Mor'du symbolizes what Merida would turn into if she became too obsessed with her anger towards her family and her kingdom.
 * Maxim Horvath: Had betrayed Merlin by allowing the sorcerer's first former apprentice Morgana le Fay to kill his former mentor soon after being broken-hearted by the fact that Veronica Gorloisen chooses his former friend Balthazar Blake as her love interest instead of him. He also disposes of his 2 new cohorts via the Parasite Spell.
 * Hopper: He enslaved the ants and then overran their island for failing to deliver the food he ordered despite the grasshoppers not needing it, with the intention of murdering their queen. He crosses the MEH when he nearly fed Dot to Thumper, sicced him on Flik, and almost killed our hero two times (nearly crushing his head and throttling him before receiving his comeuppance).
 * Charles Muntz: In a bid to clear his name after he is stripped of his membership at the beginning of the film, Muntz goes so far as to murder explorers who enter his territory. He crosses the line when he sets Carl's house on fire as he captures Kevin then almost kills Russell by dropping him out of his airship.
 * Dr. Kozak has been abducting animals and doing illegal lab tests, but he most definitely crosses the line when he injects company CEO Lance Strictland with a drug that will paralyze him for several months, giving Kozak enough time to usurp control of the company. Even his assistant scientists are horrified.

Non-Disney/Pixar Animated Films

 * General Mandible: Crossed it when he sent thousands of soldier ants to their doom and attempted to drown his own colony so he and his soldiers could rule over it with an iron fist.
 * Baron Ruber: He murders Kayley's father, Sir Lionel, in the beginning of the film. Later, he endangers Kayley's life to force Lady Juliana to follow his plan and almost kills King Arthur and Garrett.
 * Coco LaBouche: Crosses it when she tricks Chaz into marrying her and orders Kira to burn Chuckie's teddy bear.
 * Thrax: Crosses it when he burns a saliva boat and causes a sore throat after killing its crew and heats up Frank's brain. He also reveals that he murdered a little girl, a woman, and an elderly man in a gain to get his own chapter in the medical books.
 * Nigel: He enjoys torturing birds without any remorse or mercy. Likely near the end of the film where he causes a cage to fall on Jewel's wing injuring it.
 * Rameses: Vows to murder the children of the Hebrew Slaves in a bid to continue his father's legacy, then sends his soldiers to kill the escaping Hebrews while crossing the Red Sea.
 * Queen Gnorga: Crosses it when she forces Gus to turn Stanley to stone.
 * Tortoise John: Cut off Dirt's water supply, drowned Mr. Merrimack, kidnapped Beans to force Rango to hand over his gun, and betrayed Rattlesnake Jake.
 * Rattlesnake Jake: Crosses it when he attempts to kill Beans by strangling her to death.
 * Carface Carruthers: He tried to kill Charlie so he can have his own casino when Charlie was dead, which he succeeded, yet Charlie made a decision that brought him back to life. Carface also kidnapped Anne-Marie to use for his personal whims and nearly drowned Charlie.
 * Jenner: Kills his leader, Nicodemus, so he could become the new leader of the rats. Jenner also heavily refused to leave the rose bush rather than to live a better life in Thorn Valley, as promised by Nicodemus, even when Mrs. Brisby tries to warn all of the rats that they would all be killed when the NIMH organization shows up. Jenner quickly got tired of Mrs. Brisby's warnings and attempted to kill her and Justin when he came back to save her. He also killed his redeemed henchman Sullivan by slashing his chest, only for Sullivan to kill Jenner by tossing a dagger into his back before dying himself.
 * Hexxus: Ended countless lives in ancient times before he was trapped inside an enchanted tree. Once Hexxus was released from the tree, he destroyed much of FernGully with the leveler he took control of and attempted to kill all the fairies.
 * Grundel Toad: crosses it when he pulls off Berkely Beetle's wings to make sure he would help him find Thumbelina.
 * Rasputin: Almost succeeded in killing the entire Romanov family, who are avenged by Anastasia.
 * Steele: After Balto takes control of the sled team, Steele, not wanting to lose his place as top dog, sabotages Balto's path by scratching multiple trees so Balto would never be able to tell which trees were the ones he scratched to act as marks, hoping he would get lost, not caring about the other dogs, the unconscious sled driver, or even the medicine needed to save the children in Nome.
 * Kent Mansley: Rents a room under false pretenses, steals Hogarth's photos for his own use, and goes so far as to threaten to have him taken away from his mother if he does not tell him what he wants to know about the Iron Giant's whereabouts. In the climax, he lies to the army about the boy being killed by the Giant to provoke a military response and eventually subverts the chain of command by ordering a nuclear strike. When the General informs Kent that the missile will strike not only the Giant but also all of Rockwell, Mansley, revealing the true coward he is, then tries to escape only to be stopped by the Giant and arrested by the army.
 * Alphonse Perrier du von Scheck: Originally wanted to tear down Arnold's neighborhood and put a building carrying the Scheck name in order to avenge his ancestor, a governor of the British forces who was humiliated by the "Tomato Incident" (a spoof of the American Revolution). Once his plans are exposed, he attempts to run over a crowd of people, including children, with his car only to find that Arnold's grandmother has stripped his car of its tires.
 * Darla Dimple: She flooded and destroyed Mammoth Pictures Studios, blaming Danny and the other animals actors so they could get fired.
 * Lord Farquaad: Threatens to have Shrek drawn and quartered, as well as having Fiona locked back in the tower for the rest of her life.
 * Fairy Godmother: She tries to blackmail King Harold into giving Princess Fiona a love a love potion to make her fall in love with Prince Charming.
 * Soto: He tries to eat a baby alive.
 * Gutt: Attempts to kill Manny's family in cold blood, stating that the mammoth took everything he had and the evil captain intended to do the same.
 * Flashpoint Wonder Woman: After having an affair with Aquaman, his justifiably jealous wife, Mera, in a failed attempt to kill Wonder Woman, she was beheaded by the Amazonian Queen, which started World War III.
 * FLDSMDFR: It tried to destroy Flint (even though he made it), because he was trying to turn it off.
 * Chester V: Lied to Flint to get him separated from his friends, tried to kill Flint by knocking him off a cliff and into a river, captured most of the foodimals, and turned on Barb. He even broke his promise to set Flint's friends free if he dropped his sprays/weapons by trying to grind them alive.
 * Verminous Skumm: When he sold very addictive drugs that turned people into mindless zombies and ultimately killed Linka's cousin.
 * Mrs. Tweedy: Crosses the MEH by trying to use a pie machine to cook all the chickens alive into pies, just so that the Tweedy farm would have financial success. Another reason to hate her is how she ran the chicken farm like a manner of horrifying prison that contain prisoners that will given penalty anytime, as the chickens' means to survive in there are nothing more than laying eggs or be executed.
 * Lola: After Oscar dumps her for Angie, she mercilessly slams him across the windows. She then arranges Don Lino to kidnap Angie, threatening her life if Oscar does not comply.
 * Victor Quartermaine: Victor still keeps trying to kill the Were-Rabbit even though he's aware of his identity as Wallace. If anything, discovering the Were-Rabbit is the man who's seemingly stealing his girlfriend away from him makes him even more determined to kill it.
 * Piella Bakewell: She murdered a dozen bakers, and planned to murder Wallace in order to complete her baker's dozen.
 * Lord Shen: Crosses it when he committed genocide on the pandas in an effort to thwart the prophesied "warrior of black and white" from foiling his plans (which made Po believe that he was the last of his kind when he learned this). He also ruthlessly slaughtered Thundering Rhino and his own men in addition to the near-successful attempted murders of Po, Shifu, Storming Ox, Croc and the Furious Five. He even coldly killed his second in command, the Wolf Boss for refusing to fire on their own men.
 * Kai After taking the chi of every member of the furious five except Tigress, Kai wraps his weapons' chains around Oogway's statue and swings it through the Jade Palace, destroying it.
 * The Fabrication Machine: Crossed the Moral Event Horizon when it initiated the machines' omnicide against humanity, massacring and killing off the human race along with all other life on Earth via chemical poisoning. Also, after the Machine reawakened, it used the Talisman to drain the Stitchpunks' souls, and it also desecrated 2's body by turning it into the Seamstress's weapon. Although, as hinted by the Scientist, the Fabrication Machine's soullessness meant it was technically never capable of true redemption to begin with.
 * The Chancellor Fredinand: Crosses the MEH by taking the Fabrication Machine away from the Scientist, and using it as a tool to initiate another war against the economically-devastated rest of the world rather than attempt to use the Machine to repair his own country. The Chancellor also abused the Machine by pushed it beyond its limit in the construction of war machines, which is in turn what led to the Machine going insane and initiating an (initially-successful) omnicide against all life.
 * Preed: graduates from a Comic Relief supporter to all-out evil when he shoots Akima through the shoulder as she and Cale are fleeing the ship. As if that wasn't enough, he leaves Stith and Gune with communicator wristwatch-- which turns out to actually be a bomb-- which nearly kills Gune. Then he betrays Korso and holds him, Cale and Akima at Gunpoint, stating that if he kills the three before the Drej arrive, the Drej will spare his own life. After a brief fight, Preed eventually meets his end when Korso sneaks up from behind and snaps Preed's neck, killing him.
 * Chef: She tries to kill countless trolls

The Mystical Laws

 * Emperor Tathagata Killer: He has many candidates for these, but his worst action was arguably the most malign when he created tsunamis and earthquakes in order to cause millions of deaths.

X-Men Movies

 * Sentinels: Wiped out countless of races of mutants and came close to the extinction of their entire race by the end of Days of Future Past. They also had mankind suffer the same fate only because they potentially had mutant genes that were normally found in a mutant's body as well. Considering the fact that they are simply monstrous machines, they are never meant to achieve redemption since their creation.
 * Sebastian Shaw (X-Men First Class): Shaw was formerly one of the Nazi scientists responsible for perpetrating the Nazis' experiments and Holocaust atrocities on prisoners in Auschwitz. One of Shaw's victims was Erik Lehnsherr, and he qualmlessly shot Erik's beloved mother dead in front of him to enrage him into unleashing his full mutant power. Shaw would also, after WWII, attempt to trigger an apocalyptic Third World War to exterminate humanity and increase the mutants' numbers.
 * The Headmaster: Tortured and abused Russell Collins along with other mutants at his orphanage until Russell went insane and tried to kill him, if Russell had succeeded, he would have become a warlord as an adult.
 * Magneto:
 * Arguably crosses the MEH when he chooses revenge against Shaw over proving himself the better man, and subsequently tries to turn the US and Soviet ships' launched missiles on them rather than just detonate the missiles at a safe distance. This deed marked his fall to the dark side.
 * He was willing to sacrifice the teenage and helpless Rogue for his machine to work, something that Wolverine pointed out was a despicable act ("You're so full of shit. If you were really so righteous it'd be you in that thing").
 * Allows Jean Grey to turn back into Phoenix, a destructive wild creature, and he ordered Juggernaut to kill Leech despite fighting for Mutant equality and knowing that Leech was just a defenseless child.
 * In an alternate past, he nearly killed Mystique, almost drowned Logan, and used the Sentinels to come dangerously close to killing Beast, President Richard Nixon, Dr. Bolivar Trask and many other U.S. government officials.
 * Sabretooth (X-Men Movies): He provokes Logan to motivate him to become Weapon X.
 * Quill (X-Men: The Last Stand) and Psylocke (X-Men: The Last Stand): Murdered Dr. Kavita Rao and almost killed Dr. Worthington.
 * William Stryker (X-Men Movies): He manipulated Logan to make him Wolverine, captured mutant teens to experiment on, and turned Wade Wilson into Deadpool.
 * Jason Stryker: Used illusions on Charles Xavier to eradicate the human race by Cerebro 2.0., though he likely did it due to Mystique's manipulation as his original victims were supposedly mutants via his vindictive father's part before Mystique's interference. Earlier he used his mind control power as well as illusionism to make his mother commit suicide as child while he blamed his own 2 parents for his mutant condition.
 * Mystique (X-Men Movies): She reversed Cerebro so that it would target all humans, effectively coming close to annihilating the entire human race. In the past, she also tried to kill the creators of Sentinels, which brought about the near extinctinction of the entire mutant race.
 * Jean Grey: As Dark Phoenix, she killed Scott Summers and Charles Xavier, joined Magneto, and massacred soldiers on Alcatraz. Although, from Charles' explanation regarding her split personality disorder that she had due to Charles using psychic barriers on her mind to ease her control over her powers in the past, reveals that Jean Grey did not truly cross the MEH willingly, but rather crossed it due to her alternate personality (which manifests as a monstrosity that Charles identified as Phoenix) taking over her mind.
 * Lady Deathstrike (X-Men Movies): She captured Scott Summers and Charles Xavier and attempted to murder Wolverine.

007

 * Ernst Stavro Blofeld: Tried to sterilize whole humanity via a virus.
 * Let Chiffre: It is implied that he was a major conspirator in 9/11, he later tortures Bond to try and get money he owes to terrorists.
 * Elliot Carver: Tried to start a war between the UK and China and ordered to kill British fleet soldiers just to get record ratings.
 * Auric Goldfinger: He betrayed his partner in crime who was nothing but loyal to him and left him to die in a nuclear blast.
 * Alec Trevelyan: He used Golden Eye to destroy a Russian station and tried to do the same with London.
 * Gustav Graves: He attempted to devastate Japan and USA by Icarus.
 * Max Zorin: He crosses it when he kills all his mine workers to further his plan.
 * Franz Oberhauser: He killed his father out of jealousy for how he favoured James Bond, and staged his own death in an avalanche.

Jurassic Park

 * Dennis Nedry: Crosses this in a petty manner by deactivating every single security system in Jurassic Park just as means to stealing some vials of dinosaur DNA for a company where he was truly affiliated with. Though this was the only purpose, his actions inevitably caused death to some humans in Jurassic Park and his own at the hands of a Dilophosaurus whom killed him and unknowingly foiled his plans to escape.
 * Peter Ludlow: Hiring a group of hunters to capture dinosaurs and even harming a baby T-Rex just for recreating Jurassic Park against John Hammond's wishes which fearfully could cause disaster that would be worse than in Isla Nublar.
 * The Indominus rex: Killed her own sibling and murdered people and dinosaurs for sport.
 * Eli Mills: Crosses it when he left the DPG to die in Isla Nublar by using the eruption of Mt. Sibo, and kills Benjamin Lockwood later on. He is also infamous for poaching dinosaurs.

Marvel Cinematic Universe

 * Thanos: Although he adopted her and treated her as a daughter, he killed Gamora's family and tortured her until she became a living weapon. He also used Loki to bring the Chitauri on Earth. In the film, Avengers: Infinity War, he sacrificed his own daughter, Gamora, just so he could get possession of the Infinity Soul Stone so he could complete his Infinity Gauntlet so he could succeed in his goal, the random murder of half the universe's population.
 * Loki: He made a deal with Laufey only to double-cross him and take over Asgard. He later killed 80 humans and brought Chitauri to Earth to invade.
 * Obadiah Stane: Obadiah breaks into Tony Stark's house, paralyzes Tony, and steals the miniature arc reactor powering his heart, nearly killing Tony. He also reveals to Tony that he was the one who ordered the hit on him in Afghanistan. He later uses the stolen arc reactor to power his Iron Monger suit.
 * Abomination: He killed a policewoman on his way to Samuel Sterns, he later intimidated him into giving him Hulk's strength, accidentally causing his own mutation.
 * Thunderbolt Ross: He hunted Hulk throughout America, gave Blonsky the super soldier formula, and captured Banner. His action in giving Blonsky the super soldier formula ultimately backfires with Blonsky's mutation.
 * Red Skull: The Skull definitely crossed it when he killed a man to obtain the Tesseract and then destroyed a nearby village for the fun of it. The reasons why he easily crosses the MEH was not simply because he was evil from the start, but also as the side effect of the imperfect super soldier serum that the reluctant Erskine gave to him that not only caused him to become stronger, but also far eviler than he originally was and thus unable to gain redemption.
 * Aldrich Killian: He crossed it after destroying Tony Stark's home, killing Maya Hanson, and then capturing Pepper Potts (while subjecting her to the Extremis in the process) and the President, nearly killing them both. Kilian's action in subjecting Pepper Potts proved to be his own undoing, as Extremis-enhanced Pepper suddenly came to Tony's aid before he could deliver a final blow on an already crippled Iron-Man.
 * Malekith the Accursed: Crosses the MEH when he orders Kurse to execute Thor's mother, Frigga.
 * Kurse: Crosses the MEH when he kills Frigga under the orders of his master, Malekith, and then nearly kills Loki.
 * Alexander Pierce: He crossed it when he killed his maid/housekeeper when she caught him having a conversation with the Winter Soldier about HYDRA operations in his home. Worse, his Project Insight, albeit foiled by Captain America, proved disastrous due to making S.H.I.E.L.D nearly cease to exist.
 * Ronan the Accuser: He betrayed Thanos and kept the purple Infinity Stone for himself to commit genocide upon the Nova Corps. However before the film, it is stated that he had committed many genocides and killed Drax the Destroyer's wife and daughter, and during his battle with him, he told him that he doesn't care to remember and he'll forget killing him as well, but when he does recall later, he only regarded that their screams were pitiful. When the Infinity Stone is removed from his warhammer and Quill grabs it, Ronan only shows a sadistic smile. All of this makes him one of the most monstrous, psychotic, and despicable villains in the Marvel Cinematic Universe alongside Kilgrave.
 * Darren Cross: For no reason at all, he killed his associate Frank with an imperfect shrink gun. He also forced his former mentor Hank Pym out of his own company, Pym Technologies, with the intentions of replication his work for military purposes and tried to attack Scott Lang's daughter Cassie and Officer Paxton in retaliation for the destruction of the company.
 * Ego : While reluctantly placing a brain tumor in Peter Quill's mom, Meredith Quill, because he saw falling in love with her would be a weakness for him bad enough, Ego had callously crosses MEH by killed most (if not all) of his kids because they lack Celestial genes, which takes us to his main goal: to give birth to a child with Celestial genes (i.e. Peter Quill/Star-Lord) and, together with the child, kill everything in the world and make the world theirs, committing cataclysm.
 * Grant Ward: In an episode of Agents of S.H.I.E.L.D., he shot Victoria Hand and two other loyal S.H.I.E.L.D. agents in order to free his mentor and fellow HYDRA double-agent, John Garrett, revealing his allegiance to HYDRA.
 * Kilgrave : As arguably one of the most evil villains in the Marvel Cinematic Universe (though his evil nature remained inferior compared with Ronan's), he repeatedly raped Jessica Jones and Hope Schlottman and made the two his personal slaves. Kilgrave used his mind control powers to force Jessica to kill an innocent woman and made Hope commit matricide and patricide by killing both her parents.
 * Ellen Nadeer : In order to prove her loyalty to the Inhuman/Human first hate group known as the Watchdogs, she murdered her own brother, Vijay Nadeer.

Other Films and Books

 * Idi Amin (The Last King of Scotland): In reality and in the movie, Amin was responsible for murdering thousands of innocent Ugandans and even went so far as to mutilate his own wife for being unfaithful.
 * Colonel Richard Strickland: Mercilessly tortured the Asset and tried to murder Elisa and her friends.
 * Vilos Cohaagen: turns off the air in a sector on mars that almost kills the mutants living there.
 * Captain Vidal: Notorious for murdering innocent civilians to root out anti-fascist rebels, Captain Vidal is responsible for many horrendous acts throughout the lion's share of the movie. He kills a peasant boy in front of his own father and shoots them both in cold blood. He even tortures a stutterer, maltreats Ofelia, and kills the town doctor for showing remorse for him. At the end of the story, he steals Ofelia's infant brother for himself and fatally shoots her in the chest without a hint of empathy before receiving his comeuppance.
 * Count Grisham: He attempted to murder the Scarecrow by burning him alive, and planned to take away Polly's money before sending her and the other orphans back to the mill, but he finally crossed the line when he decided to murder Polly for rejecting him. Notably, this is what drives Wooden to finally leave his side.
 * Grimm Jim: He terrorized Cole Junction and crossed the MEH when he murdered Judy Muskrat's husband, who owned the town saloon, taking over the business. Then, after losing a match with Bulletproof Jackson, he shot Old Drunk George and kidnapped Ashley before attempting to shoot our hero in the head.
 * Millicent Clyde: In a bid to redeem the good name of her father, she hunted down Paddington in an attempt to kill him and put him on display in the British Museum.
 * Javed Khan: He forced Salim to work for him against his will and used Latika as one of his concubines.
 * Lisa: It is debatable if she really crossed it since she showed remorse, but she may have crossed it when she cheated on Johnny (the Main Protagonist) with his best friend Mark, causing Johnny to reach the Despair Event Horizon and commit suicide.
 * Richard Bagg: Framed Van Wilder by bringing underage children to one of his parties and getting them drunk and cheated on Gwen with Jeannie.
 * Marion Hawthorne: If reading Harriet's notebook is not bad enough, initiating the blue paint incident is definitely what does it.
 * Dr. Heiter: Cross it when he makes a 3 person centipede out of 3 people and he killed 2 detectives.
 * Martin Lomax: cross it when he killed his mom with a crowbar and just like Dr. Heiter he makes a 10 person centipede out of 10 people instead of 12 people and he kills all the people with a gun and he slit their own throats expect for 2 people who one is presumed alive after Martin silts her throat and the other is still alive after Martin fails to get her out of the car and it'is unknown weather or not it was a dream.
 * Dwight Butler: and Bill Boss: Dwight for suggesting the longest centipede ever. Bill was already too far into the horizon once he decided to put it into motion and Bill Boss killed Dwight Butler with a gun.
 * Hans Gruber: Holds a party hostage for ransom and kills a member when they stated that they were friends with John McClane.
 * William Stuart: Crossed it when he caused plane full of people to crash on the runway, killing everyone onboard.
 * Nicholas Wyatt: Crosses it in having many people that failed at getting information for him killed.
 * Bob Barnes: Shoots Sargent Elias and leaves him to die in Vietnamese war ground just so he would not report him on war crimes.
 * Norman Osborn: Wanted to weaponize Richard Parker's research for foreign countries, thus he tried to betray his country for his own benefits and profits. When Richard tried to destroy his work and escape with his wife, Mary, Norman sent his man to kill them both and also faked evidences against Richard in order to discredit him.
 * Ashley Kafka: Treated his patients with extreme malice and cruelty by sadistically torturing them and remorselessly experimenting on them.
 * Carter Burke: Cross it when its discovered that the reason behind the mission was to collect samples from the aliens even though he were well aware that's basically a suicide mission.
 * Auric Goldfinger: Crosses it when he betrays odd job and leaves him and other henchmen to die in the gold vault.
 * Harvesters (Independence Day): Although destroying most of the world's major cities and killing countless innocents is horrible in and of itself, they truly cement themselves as irredeemable when one of them reveals their plan to wipe out all life on Earth in order to milk it of it's natural resources, and that peace is not an option. They also revealed having done the same on countless planets in the past before did the same on Earth.
 * Howard Payne: When on the the phone to the movies hero just to prove he was not joking about bombing the city he blew up a bus full of people.
 * Pete Davis: By killing his partner Roy Cole to prevent him from reporting his obsessive behavior.
 * Owen Shaw: His willingness to harm or kill innocent civilians during the penultimate chase (in a rather monomanic and sickly satisfying way) either just to get away or to spite the heroes and get them to back off. Threatening Mia's life to secure his escape and showing no loyalty to any of his underlings or associates (making him a complete foil to Dom) further cements it.
 * Cipher: Blackmails Dominic "Dom" Toretto to kill his baby son.
 * Bill Cox: When he tricks Andy Stanfield into eating a cookie with nuts as an ingredient (knowing he is allergic) in order to force Jack to fully submit to helping him. Or when he kills Jack's friend Harry Romano as a means of setting up Jack not only for his murder, but for orchestrating the bank robbery.
 * Simon Phoenix: Committed heinous crimes, such as murders and rapes, to the point of becoming the most crazed and dangerous criminal of the 20th Century.
 * Richard Detmer: He abused his own son Andrew Detmer and even tried to kill him over an arrogant, selfish, hypocritical reason. This eventually led to Andrew's Despair Event Horizon.
 * Dr. Herman Varnick: Tried to shoot George Newton for interfering with his plans to kill Beethoven, only to have a Jack Russel Terrier named Sparky bite the vet and cause him to misfire.
 * Clarence Darby: Committed a violent home invasion with his partner, Rupert Ames, which resulted in killing Clyde Shelton's wife and daughter. Taking advantage of the lack of physical and testimonial evidence, he pinned most of the blame on Ames, which resulted in Ames getting the death penalty and Darby getting 3 years. This resulted in Clyde Shelton becoming a violent vigilante by killing a majority of the Justice Department, Rupert Ames and Darby himself (in a very graphic way).
 * Buggy Ding Dong: Tried to kill Smoochy the Rhino with his sniper rifle during the ice show before he was stopped by Rainbow Randolph. Burke Bennett, Frank Stokes, and Merv Green of the Parade of Hope Foundation also cross it by arranging the death of Smoochy, which also killed Moochy (Spinner Dunn) and enraged his cousin Thomasin "Tommi" Cotter and the Irish mob, which lead to all of their deaths or being at the mercy of Tommi Cotter.
 * Frank D'Amico: Crosses the Moral Event Horizon when he orders Kick-Ass and Big Daddy to be captured and publicly executed on a video streamed live across the entire internet. Both Kick-Ass and Big Daddy are viciously beaten, and were almost burned alive. Though Kick-Ass managed to survive (due to the timely intervention of Hit-Girl), Big Daddy was killed after suffering severe burns.
 * Chris D'Amico aka Red Mist/The Mother F**ker: In Kick-Ass 2, he orders his men to kill Dave's father and then texts Dave a picture of his corpse, although he may have crossed it earlier when he killed Colonel Stars and Stripes and had Night Bitch beaten; in the comics he crosses it when he rapes Katie Deauxma and murders 4 children.
 * Boris the Animal: Goes back in time and murders Agent K. His past counterpart murders Agent J's father.
 * Castor Troy: Killed Sean Archer's son Michael. Even though he admitted that it was an accident and that his target was Sean Archer himself, Castor showed no remorse.
 * Chucky: Murders Tiffany for leaving him. This drove his son, Glen, crazy, who then kills Chucky for doing this.
 * Calvin Candie: Giving the order to have the dogs release and eat alive a poor, weak, and blind slave for his escape and refusal to fight.
 * Alex (A Clockwork Orange): When he broke into the Alexander's home, beating both of them and then striping Mrs. Alexander naked and raping her in the infamous "Singing in the Rain" scene. This has always been the subject of debate, since in both the book and film, Alex is put through monstrous experiments to cure him and when he runs into Mr. Alexander again, the now crippled writer tortures him for revenge.
 * Alan Garner: Crosses it in the second Hangover film when he drugs the Wolfpack yet again, this time on purpose and with the intention of knocking out Stu's future brother-in-law, and lies to his friends about it. If not then, then in III when he causes his father's fatal heart attack through his stubborn insubordination or setting Chow free before the Wolfpack brings him to Marshall, which results in Marshall thinking he was screwed over and nearly killing them all.
 * Spider (Gran Torino): Crosses it when he kidnaps and his gang rapes his own cousin Sue Lor.
 * Horace Pinker: He has crossed it when he starts to kill innocent people and children and he almost killed his own family expect his own son.
 * Harry and Marv: Cross the MEH in Home Alone 2: Lost in New York, when they plan to rob Duncan's Toy Chest of all the money that was intended to go to the children's hospital on Christmas; as commented by Kevin, "You can mess with a lot of things, but you can't mess with kids on Christmas!" They also tried to murder Kevin in Central Park as payback for all the deadly traps he'd sent them through, and tried to shoot the pigeon lady when she intervened.
 * Johnny Bartlett and Patricia Bradley: Cross it before the film when they killed all the doctors and patients in a hospital, even the ones in a chapel. They further cross it after Johnny's death when he, as the Grim Reaper killed Frank Bannister's wife, and Patricia carved the number 13 on her forehead as a mark of Johnny's thirteenth victim.
 * John Doe: He killed several people in gruesome ways. Yet, when he finally appears and gets caught, he is somewhat sympathetic to the protagonists, enough to be an anti-villain. However, it is revealed that he raped and killed (through decapitation) the pregnant wife of David Mills.
 * Kaptain Krazee: For years he has been stalking Chris, but he crossed it when he locked Chris in a box and turned him into a clown permanently.
 * Danny McBride: Crosses it in This Is The End when he tries to shoot his friends, not knowing the gun is loaded with blanks. He crossed it again when he, one became the leader of a pack of cannibals, tries to devoured his friends though only succeed in devouring James Franco.
 * Jonah Hill: Crosses it in This Is The End when he prays to God for Jay Baruchel's death, which ended up led God leaving him for raped and possessed by Incubus for the rest of the film.
 * Mayor Augustus Maywho: He offers the Grinch a shaver as a Christmas present just to deliberately humiliate him during Whoville's Christmas celebration and remind him of his tragic past since he made fun of the Grinch's facial hair and shave job back when they were kids in school. He even proposed to his childhood love interest, Martha May Whovier, in front of him. After all of this caused the Grinch to go on a rampage, the Mayor gets the town to have Christmas "Grinchless". Also, after the Grinch stole all of the Who's presents and decorations, he accuses Cindy Lou Who for inviting the Grinch in the first place.
 * Ghost (Ginger Snaps): Locks a desperate Brigitte Fitzgerald in her basement as she turns into a werewolf, with intentions of using her to kill people she doesn't like, starting with her grandmother.
 * Ozymandias (Watchmen): Successfully destroying New York City with an artificial alien and killing roughly two million people. The movie ups the ante by expanding the attack to several cities around the world and increasing the death toll to about 15 million. This is a legitimately arguable and subjective example, due to Veidt being an anti–villain.
 * Cal Hockley: Crosses this few times during the Titanic's sinking, he first frames Jack for stealing the heart of the ocean and shortly and when Rose gets onto a life boat, he tells Jack that he is very willing to leave him to die. When Rose refuses to leave Jack behind he attempts to kill them both.
 * Richard Fenton: Kills just about every person acquainted with Donna Keppel (including her family), so that he could have her all to himself.
 * Kurt Bozwell: Poisons Ed's secret sauce, hoping to have Good Burger shut down.
 * Kenny: Threatening to push Owen through the ice.
 * Esther Coleman: She crosses it when she stabs John to death, as Max watches in horror.
 * Principal Agatha Trunchbull: Miss Trunchbull is responsible for the graphic and unspeakable torture of her students, not above throwing them out the window or locking them in the Chokey if they fail to pay her respect. She also abused her niece Jennifer Honey when she was only a child, and is implied to have murdered Jennifer's father.
 * Destoroyah: Mortally wound and seemingly killed Godzilla's son Junior by dropping him from the sky and then blasting him with his micro-oxygen beam (though Junior resurrect himself after his body reacts and absorb radioactive energy from his dying father).
 * Debbie Jellinsky: Killed her parents at a young age just because they didn't give her the barbie doll she wanted.
 * Jennifer Check: Killed Chip, the boyfriend of her best friend Anita Lesniki.
 * Khan Noonien Singh: Savagely tortured and murdered the innocent scientists working on the Genesis project, just so that he could score a blow over Captain Kirk.
 * Nancy Downs: Her attempts to get Sarah Bailey to kill herself qualify.
 * Chris Hooker: Either crosses it when he spreads rumors that Sarah had sex with him when she didn't (evidently did the same to to Nancy) or when he attempted to rape Sarah. More so the former as he was under an obsessive love spell for the latter.
 * Adolf Hitler (Downfall): Though this version of Hitler is rather sympathetic, it does not excuse him from his war crimes.
 * Damien Thorn: Crosses the Moral Event Horizon when he murders Mark, his own cousin and adopted brother, for refusing to join him. Although, while this was the point when Damien crossed the MEH, his unholy and inhuman origins and nature, and/or his destiny's biblical inevitability meant there was arguably never any hope of redemption for Damien to begin with.
 * Mrs. Carmody: In the film, she and her followers cross the MEH when they savagely turn on a terrified Jessup and send him out into the mist in cold blood to be killed by one of the creatures.
 * Clarence Boddicker: In RoboCop when officer Murphy gets lost in the mill he shoots him to death for fun that causes Murphy to become RoboCop.
 * Cliff Vandercave: When the Dictabird exposes his embezzlement scheme to Bedrock, an enraged Cliff kidnaps Pebbles & Bamm-Bamm and traps them on a giant mining machine, in exchange for the Fred & Barney to give him the bird back. Even when Fred and Barney give him the Dictabird, Cliff goes back on his word and starts the machine to kill Pebbles & Bamm-Bamm, leaving Barney to go save them. Cliff then attempts to shoot Fred, but Miss Sharon Stone knocks him out with a money bag. Cliff tries to escape the cops, only to look up and spot a huge amount of molten concrete as it buries him alive, turning him into a statue.
 * Happy Chapman: steals Odie for his own gain, then uses a dreaded shock collar on him to force him to do tricks and even laughs at the dog's pain from the powerful jolts (despite his assistant Wendell reminding him that he'd promised he'd never use the collar, claiming it to be "inhumane.")
 * Jason Dean: he crossed it when he trick Ed all the students into signing a petition to blow up the school and then tries to blow it up during a pep rally with hundreds of people inside. *Emil Houchen: crosses mere minutes into the movie when he remorselessly kills a homeless man for excitment. He then brutally beats a henchman because the homeless man had kids not because of moral qualms but because of unneeded attention. *Sheriff of Nottingham: Crosses it when he kills Robin Hood's father for refusing to join him in his courrupt reign. He also tried to execute all the captured prisoners (Little John's son included).
 * Gordon Gekko: crosses it when tries to bankrupt Carls company just to get more money and doesn't care about all the workers he'll put on the street.
 * Biff Tannen: Crosses the MEH when he tries to rape Lorriane and tries to beat up George McFly when he tries to stop him, and attempts to run Marty over with his car.
 * Frank Nitti: Crosses it when he coldly kills Malone and toughts eilloit saying "he died like a stuck irish pig. Now you think about that Whilei beat the rap".
 * Alex Forrest: Crosses it when she boils the children's pet rabbit alive just to get back at Dan, not caring about the kids who would be effected more than him.
 * Walter Peck: Crosses it when he burges into the ghostbusters office and demands the power grid to be turned off which causes an explosion and then tries to arrest the ghostbusters even though he was clearly responsible and was warned exactly that would happen by the ghostbusters.
 * Mulgarath: In the book series, he kidnapped the Grace children's mother and callously murdered the dwarves. Later, he tried to kill Jared, Simon and Mallory and planned to dominate the human and fairy worlds.
 * Tommy Udo: In the famous scene, he crossed the MEH when he took sadistic pleasure in shoving the old woman in the wheelchair downstairs by killing her.

American Dad!

 * Stan Smith: Stan arguably crossed the MEH when he had his own family's lives ruined just so he could take revenge on a car salesman who cheated him in a deal.
 * Francine Smith: Trapped Akiko in the basement and tricked Steve into thinking that she didn't love him anymore just so that he could win the spelling bee (for her personal gain).
 * Roger: Had an obsession with Hayley in the episode Love AD Style, eventually capturing her and attempting to cut off her skin and wear it. Also in the episode Virtual In-Sanity, he ran over five innocent people just because they didn't pay him twenty dollars.
 * Ricky Spanish: Framed Steve for a crime and got him locked up even though all Steve was trying to do was get Ricky to redeem himself.
 * Steve-arino: Kills, and tortures neighborhood cats, and kidnaps Steve Smith with intentions to kill him and replace him among the Smith family.
 * Emperor Zing: Keeps a ship full of alien slaves from many planets, keeping each of them separated from their true love, and has them take a test to prove it, and castrates those who fail.
 * Lorraine: In "Flirting With Disaster", she throws acid in Francine's face.

Total Drama

 * Heather: Crosses it when she plays her cruelest trick on Gwen by kissing Trent, Gwen's love interest, to make it look like Trent was cheating on her, leaving Gwen very upset and since Heather wins immunity in the end of the episode Trent ends up eliminated. Also when she won the bike challenge, she betrays her friend Lindsay, causing her to lose in a bike race and get voted off. She admits she was using her and was never her friend. She also definitely crosses this in Total Drama: Revenge of the Island when she steals the million dollar prize and hijacks a zeppelin to escape, but failed.
 * Chris McLean: He crossed this in "Action", where he only cared about the contestants surviving the flooding submarine challenge in "Masters of Disasters" and escape drowning only so that he could still get his paycheck and keep his "luxurious lifestyle".
 * Alejandro: Crosses it in the finale of TDWT by nearly killing Cody by knocking him in to the shark infested waters.
 * Courtney: In "Sundae Muddy Sundae", she REALLY crosses it when it's revealed that after everything Gwen's done to make up for her kissing Duncan, she never actually liked Gwen and only pretended to be her friend to get to the finals.
 * Mal: Mal crosses this many times as part of his sociopathic persona, such as imprisoning Mike and his personalities inside his mind, attempting to hurt and kill multiple contestants for no reason, sadistically watching Zoey almost get painfully eaten alive by piranhas, and would have allowed it if he could keep his cover as Mike. He then later attempts to mentally break Zoey by constantly taunting her about Mike being gone forever.
 * Amy: Crossed this in record breaking time when in the first 5 minutes of the first episode she tries to kill her sister by kicking her off her leg while they were parachuting, and was even annoyed that Samey's parachute worked.
 * Scarlett: She crossed the line when she threatened to allow Pahkitew Island to self-destruct and kill the remaining contestants unless Chris gave her million dollars, but failed.

The ​Fairly OddParents

 * Vicky the Babysitter: The episode Scary GodCouple depicts her being much sinister than her usual standards; when Foop is assigned to be her fairy, she wishes for the cancellation of weekends, summer vacation, and birthdays; as well as for the children of Dimmsdale to be tormented by monsters and be trapped in lockers. She also treated Foop very harshly through the episode, to the point of making him cry and eventually helping Timmy defeat her.
 * Mr. Crocker: In Abracatastrophe, he kidnaps Cosmo and Wanda and uses their magic to control the Universe. He threatens to turn Timmy's parents into ice sculptures and transport them into the sun (which would literally kill them) if Timmy didn't surrender.
 * Remy Buxaplenty: Although he tried to get rid of Timmy's fairies repeatedly due to jealousy, the worst way was tricking Timmy, Chester, and A.J. into attending a military school, locking up Cosmo and Wanda (in fish form) in a confiscation shed and trapping them in a butterfly net (which is a fairy's weakness), and tried to blow up the shed and destroy Cosmo and Wanda. (through Shallowgrave). But luckily, Timmy and his friends managed to save Cosmo and Wanda and Remy and Shallowgrave got their payback (by being hit with the same rockets that were going to be used on the shed).

Family Guy

 * Peter Griffin: Threw an unconscious Stewie with heavily infected head wounds underneath Lois' car so she would run him over, after weeks of no medical treatment, just so she wouldn't ask how Stewie got hurt.
 * Stewie Griffin: He crosses the line when he nearly kills his mother, frames Peter Griffin after his friends begin to believe that he was the killer, takes his entire family hostage when his secret was uncovered, and finally takes over the United States as a dictator by threatening to destroy their power grid. Though this was later revealed to be a simulation, he was not horrified by what his simulated counterpart had done.
 * Cleveland Brown: On The Cleveland Show, after Rallo almost drowns and blackmails Cleveland for it, Cleveland dunks Rallo's head in the pool twice just so Rallo would stop bossing him around.
 * Carter Pewterschmidt: In "The Old Man and the Big C", it is discovered he has held the cure for cancer since 1999 but has refused to reveal its existence to maximise profits. When Lois tries to convince him to reveal it by asking him what he would do if his loved ones had cancer, he agrees to tell the public. However, he only reveals the existence of a new deodorant and has not revealed its existence, caring more about money than his own family.
 * Diane Simmons: She turned insane when Tom Tucker replaced her with a younger woman at the news and James Woods dumped her. For revenge, she swore revenge against theme. She accidentally Stephanie who was sitting where the gun planted by Diane would hit James Woods. During a black out, she killed James Woods with a knife, but Muriel Goldman and James Woods' wife Priscilla had discover that she was the killer and so she killed them, later she hit Derek Wilcox with a Golden Globe, she she put him under the Tom Tucker's bed, indicting him for everything. When Lois discovered her plan, Diane decided to kill her.
 * Bertram: Murders Leonardo da Vinci in order to kill his delayed offspring, Stewie. When told that by committing the murder that it might destroy the universe including him, he says that it was worth it and shoots him with the arrows.
 * Jeffery Fecalman: He verbally and physically abused Quagmire's sister Brenda for years, but he crosses this when he tried to strangle Quagmire to death.
 * Brian Griffin: He gives Stewie and Chris Griffin herpes by transmitting blood, knowing very well that he himself has the incurable disease and kept it a secret from them. He REALLY CROSSED it when he Brian gets a job as a real estate agent after undergoing surgery. He cons Quagmire into buying a run-down apartment loft, despite the fact that he consoled and helped Brian earlier in the episode. Later Brian apparently comes to the realization of his actions and admits what he did was selfish and pretentious - until revealing it was part of his devious plan.

Mucha Lucha

 * El Malefico: He crossed it when he controls The Flea into tricking Rikochet to reading a sentence from the code of masked wrestling backwards thus setting him free and El Malefico defeats all of the luchadores and sealing them in the code of masked wrestling book thus increasing his powers and he tortures them and turning the singer's wife into dust and he almost killed Rikochet, Buena Girl, and The Flea.
 * Masked Toilet: The masked toilet crossed it when it attempts to kill The Flea's baby sister Pulgita and Masked Dog and it also defeated Rikochet, Buena Girl, and The Flea.
 * Misterioso Grande: He crossed it when he started to take away everyone's masks while they were sleeping and when he shows them their fear.

Akame Ga Kill

 * Seryu Ubiquitous: Fatally wounds Sheele, and feeds her to her Teigu (earning both Mine and Tatsumi's personal grudge). She crossed it even further in her final battle with Mine, by making a derogatory remark on Sheele being a "purple freak", and was happy to be the cause of her death.

Higurashi no Naku Koro ni

 * Shion Sonozaki: Torturing and murdering Satoko in the Meakashi-hen arc of Higurashi no Naku Koro ni and forcing her sister Mion to watch. Even she admits that she's irredeemable at that point.
 * Teppei Hojo: Was a child abuser who kicked and threw around his niece Satoko onscreen while she is crying.
 * Rina Mamiya: Not only does she gleefully contribute to Teppei's schemes, but she also tries to strangle Rena Ryuuguu to death with her bare hands when she blows Rina's cover and tries to protect her father.
 * Miyo Takano: She kills Rika's parents, the protagonists, her own boyfriend, and infects the entire village with the disease.

Elfen Lied

 * Lucy: Frequently killed countless people (especially while invading their homes at night as a child). Eventually, she even murdered Kouta's sister and father out of envy.
 * The Bullies (particularly Tomoo): Although minor villains, the bullies are highly remembered by many in one of the most hated scenes in anime and can be considered as one of the worst known Moral Event Horizon Crossers where they bullied Lucy for fun & brutally killing her pet puppy on purpose by forcing her to watch without any remorse, thus causing their own demise. They are also responsible for turning Lucy into a murderous psychopath. Worse, it is also implied that they could have turned into a serial killer even far worse that Lucy herself and exactly much like that of the Unknown Man if they weren't slain in the process.
 * Unknown Man: Crosses it by raping and mutilating Diclonii. Among other things, this involved having a surgeon remove the lower half of Number 28's body so he could easily carry her around inside a backpack & keeping her inside a special tank that left her excruciating pain, unable to use her powers against him. He also cut her vocal cords, leaving her in vain, injects her with a drug that gives her 3 hours to live & uses her as a tracker to find Lucy. When he finds Nana instead, he kicks over her container in fury, which finally kills her. He does it once more by barging into the Maple House, proceeding to incapacitate Nana by firing a poisoned spiked iron ball from a crossbow on her, nearly killed Wanta by kicking him & would have raped and murdered Mayu (and very likely Nana as well) if it hadn't been for Bando's intervention, who was shunned by this. This makes him one of the most evil and cruel villains of Elfen Lied.
 * Director Kakuzawa: He raped and impregnated Lucy's mother with the intent of having Lucy have a child with her half brother and have a child which he would use to wipe all humanity and repopulate the planet with his descendants in order to be worshiped as a god by future generations.

Pokemon anime

 * Grings Kodai: Crosses it by electrocuting Zorua to near-death, then directly killing Zoroark in front of Zorua.
 * Hunter J: She sets a forest full of Pokemon on fire in order to steal a frightened Riolu (which could have been fatal if Blastoise hadn't been there to use Rain Dance), tries to kill Ash by setting the already-burning forest around him on fire, later lets him get to her room in her ship so she can attempt to crush him with Drapion, and later sends him falling to his doom. She ends up being one of the few Pokemon villains to die many episodes later.
 * Cyrus: Possesses the Lake Trio, Dialga, and Palkia in an attempt to create his own dimension while destroying Earth. He even leaves his own teammates to die, saying they'd poison his new world. Ironically, it is he and his own dimension who end up being destroyed in the end, and despite him leaving her for dead, Mars is sad to see him go.
 * Damian: Abandons his Charmander then refuses to return for him after it begins to rain and threatens to put his tail flame out (which will kill him).
 * Mayor of Trovitopolis: When he was a child, he abandoned his Bulbasaur in sewers because it wouldn't evolve.
 * Iron-Masked Marauder: Remorselessly crosses it in torturing Celebi into submission before brutally crushing Ash's hands.

Code Geass

 * Charles zi Britannia: He conquered most of the planet and sacrificed many lives to become immortal and deform it.
 * Lelouch Lamperouge: He used the Geass power on his friends and relatives, killed many bad guys, but he accidentally made Euphemia li Britannia kill innocent Japanese people and used this massacre in his propaganda. He also declared the global war and conquered the whole planet by threatening to use 2 most powerful weapons of mass destruction.
 * Schneizel El Britannia: He turned Black Knights against their founder Lelouch, and manipulated Suzaku, Lelouch, and others to be seen as the only hope for the world, when he wanted to conquer it. Ironically he used Black Knights to fight in his final war.
 * Clovis la Britannia: He ordered to kill innocent people
 * Cornelia li Britannia: She crushed many rebellions in her empire
 * Marianne vi Britannia: She started a war with Japan, no longer caring for her children in that nation and tried to deform the world.
 * Suzaku Kururugi: In spite his noble goal to bring Britannia Empire to the good side, he crosses it by betray his own Japanese people to serve Britannian Empire as well as had Lelouch given false memories by Charles.

Kids Next Door

 * The Delightful Children From Down the Lane: Were responsible for the removal of Nigel Uno/Numbuh One's hair. This one was only played for laughs, but is treated as "unforgivable". According to an episode of Villainous, this was done using the Head of Quetzalcoatl.
 * Father: Attempts to cook the children who competed in the competition for the Delightful Children From Down the Lane's annual birthday cake into a cake and let them eat it.
 * Chester: Opens a fast food restaurant called Burger Frenzy, where kids visiting the restaurant are captured and used as the meat on burgers which are then sold to sharks.
 * Grandfather: Was once the complete ruler of the world and forced every child (including his sons, Monty and Benedict Uno) to work in Tapioca factories for him. Once he was recommissioned, he shunned his son Benedict (now known as Father) as a complete and utter failure and betrayed all the other villains by turning them all into Senior Citi-zombies. It is also implied that he was the reason for Father's fear of broccoli.

The Avengers: Earth's Mightiest Heroes

 * Red Hulk: Thaddeus Ross hunted Hulk for years and framed him for becoming Red Hulk. Later, he catches him and locks him up for months. He also inserted a chip into Bruce Banner to lose control and and make everybody believe that he is a monster. When Ross was finally arrested, he still considers himself a hero and still hates Hulk just because it is different.
 * Red Skull: He has forced Bucky Barnes to do horrible things, making him a criminal.

The Boondocks

 * Ed Wuncler, Sr.: Masterminds a terror attack on Wuncler Plaza to kill one man so he can profit from his image.
 * Ed Wuncler II: Forcing people in his debt to work at slaves in his slavery theme park Freedomland, no matter their race, and when Huey Freeman defies him, he attempts to have Huey's foot publicly cut off.
 * Lamilton Taeshawn: Stole his grandmothers car so he and Riley Freeman can cause trouble. He also beat up his grandmother and shot a tied up dog of a woman he was planning to rob and tries to kill Riley for avoiding him.
 * Uncle Ruckus: Aides in reinstating slavery, and helps Ed Wuncler II run a slavery themed park called Freedomland to act as a slave owner with sadistic and raciest glee.
 * Mister Ruckus: Took his hatred for white people out on his son Uncle Ruckus, and kicking him out of their house at a young age. This, combined with his wife's praise of white people, and convincing Uncle he is really Caucasian, is what made Ruckus hate black people.

Sword Art Online

 * Akihiko Kayaba: Cross it by prevents the whole SAO players from returning to the real world at the beginning of the series and giving them the challenge to defeat his avatar as the only way to return to real world.
 * Nobuyuki Sugou: Prevents around 300 SAO players from returning to the real world in order to use them as test subjects for his research on controlling peoples' feelings, memories, in other words, research on the manipulation of the human soul. Holds Asuna hostage in the virtual world, sexually harasses her in front of Kirito and threatens to rape her. Tries to kill Kirito and tortures him by turning the pain absorber program level down so that Kirito would experience real pain from the injuries. Later tries to kill Kazuto in the real world. This MEH actions proved to be far more sinister and depraved compared with Akihiko's own crossing, in which the manifestation of his consciousness in virtual world decided to came to help Kirito to defeat Sugou's avatar.

Gravity Falls

 * Lil' Gideon: Because of his delusion, he tried to kill Dipper many times and he stole his uncle's house and store. He also lied to the naive people who all loved him about his supernatural powers when they were just souvenir pins with hidden cameras. His sole reason to be bad is his jerkish personality and mocking people. In his reappearance in season 2, he forcibly mind controls his father in an election and tries to blow up Dipper, Mabel, and Stan after losing the election.
 * Preston Northwest: Crosses this in "Northwest Mansion Mystery" when he was willing to let all his guests, including four children, die rather than swallow his pride and let in the common people of the town. Not to mention being extremely emotionally abusive towards Pacifica, up to and including having her trained to respond to a bell with contrition like one of Pavlov's dogs. During the apocalypse he wanted to join Bill, but instead Bill decided to put his ears where Preston's eyes should be, a single abnormally large eye in his mouth, and part of the nose where his ear should be.
 * Bill Cipher: Bill is the worst of them all; He is a demon who planned to use Ford and make him build a machine where the Nightmare Realm will fuse with Gravity Falls, causing the apocalypse. He also crosses it when he stops time and traps Mabel in a time prison bubble. His henchmen kidnap the citizens from Gravity Falls, who he turns to stone. He also kills Time Baby. He and his friends saw all this simply as entertainment and decide to party, but this was just the first part of Bill's plan.

Steven Universe

 * Homeworld Gems: The entirety of Gem Homeworld's chain of command seems to have crossed this pre-series. While they were already perceived to be a threat, having fought a large-scale war and attempted to colonize Earth with little regard to the people who already lived there, the depth of their cruelty and disregard for life had never been clearly shown until it was revealed they have been creating forced fusions out of shattered gems, essentially committing necrophilic rape on millions of other Gems. It gets even worse when it is revealed that they had given up on the Earth to instead use the planet as an incubator for a gigantic forced fusion that will destroy all of Earth once it hatches.
 * Jasper: Destabilized Garnet, head-butted Steven into unconsciousness, disregarded Peridot's orders, forced Lapis Lazuli to fuse with her, broke Amethyst's spirit, tormented numerous Gem Monsters into submission, and (worst yet) deliberately refused Steven's help when she was becoming corrupted. All of this is stemmed from the fact that "[she has] been fighting from the second [she] broke free from the Earth's crust" in an attempt to avenge her fallen master Pink Diamond.
 * Eyeball: Attempted to murder Steven, under the impression that he is in fact Rose Quartz.
 * Aquamarine: Kidnapped Steven's friends to be imprisoned in a zoo full of humans, easily overpowered the Crystal Gems, and kept Topaz in line with threats of being shattered/separated.
 * Yellow Diamond: Of all the Homeworld Gems, Yellow Diamond holds the least regard for organic life. She wants nothing more than for Earth to be destroyed and erased for their people's records by any means necessary, and for Rose Quartz (who she mistakes Steven for in the fifth season premiere) to be executed, going as far as to silence anyone who defies/objects to her desires.

Transformers: Prime/Robots in Disguise

 * Megatron: He crossed it in the season 2 finale of Transformers: Prime when the Autobots seized the Omega Keys and secured the Omega Lock (the sole device in the universe that could restore the war-ravaged planet Cybertron). In order to retake the Omega Keys and the Lock for himself, per Starscream's advice, Megatron had the Autobots' human friends taken to Cybertron in air-tight pods as hostages, threatening to open them and expose the humans to Cybertron's toxic atmosphere (and possible lack of oxygen), which would kill them instantly, unless the Autobots relinquish the Omega Keys to him. Though the Autobots did exactly this, even after Optimus Prime asked that he be allowed to return the humans to Earth, Megatron instead elected to use the Omega Lock to cyberform Earth, which would destroy all indigenous life in the process. Optimus made the ultimate sacrifice by destroying the Omega Lock to save Earth. In the aftermath, Megatron destroyed the Autobots' base on Earth, Outpost Omega-1, after having discovered its location. Megatron crosses MEH again by destroying whole Predacon Project and framing Autobots for this to avoid any possibilities of the cloned Predacons' betrayal due to Predaking's sudden developed intelligence. He manipulated Predaking further to inflict his rage on Autobots until Ratchet told Predaking the truth, which prompt Megatron to left Predaking to die in the outer space. Fortunately for the Autobots, this second MEH crossing costs Megatron more, as most of his Vehicon soldiers died at hands of Predaking before he able to rid of him. Ultimately, Megatron (after being broken free of Unicron's possession in "Predacons Rising") realizes that his quest for conquest has been for nothing, resulting in him abandoning the Decepticons forever.
 * Silas/Cylas: Crosses it when he makes a deal with Airachnid that since M.E.C.H. was seeking out Cybertronians for scientific study, he can have what is left of the Autobot Arcee, after she has terminated her, and in order to lure Arcee to them, he kidnapped the mother of Arcee's human companion, Jack Darby, as a hostage. Once Jack and Arcee arrived to rescue Jack's mother, Airachnid immobilized Arcee with her webbing. Arcee then pleaded to Silas to help Jack and his mother, since they are humans like him, but Silas outright stated that "a few humans lives are a small price to pay for a miracle of science like [herself]", and simply watched as Airachnid attempted to kill both humans. This also proved Silas to be even less human than the Decepticons. He crosses it again in the following season when he frames Optimus Prime by constructing a remote-controlled doppleganger of him, Nemesis Prime, which he first uses to try and kill the Autobots' human liason, Agent Fowler, and then turn the military against the Autobots by attacking a military base. Despite military orders to terminate all Autobots on sight, Optimus and Fowler locate Silas' base and destroy the doppelganger, ultimately clearing Optimus' name. As retribution for his actions, Silas is inadvertently crushed beneath the destroyed doppleganger he created. His troops worked diligently to save his life by integrating him into the body of the deceased Decepticon, Breakdown, the remains of whom they found prior. Though their efforts brought Silas back from the brink of death, he crossed the MEH to the point of no return by killing his own men with the intention of joining the Decepticons.
 * Airachnid: Crosses this by brutally murdering Arcee's close friend Tailgate. He also tries to kill Jack as well as make a deal with Silas in which she turned out planned to had Darby watch his mother die. Though in the end Arcee finally defeat her by trick her into Insecticon pod, freezing her in process. However, this was the beginning of Airachnid's actual retribution as due to chaos in the episode "Thirst", she ended up become a vampiric Terrorcon.
 * Soundwave: After escaping the Shadowzone in his Robots in Disguise debut, he tried to summon an army of Decepticons to Earth. Later in Combiner Force, he manipulated Activator Mini-Cons and Steeljaw's pack to steal Decepticon Hunters and nuclear waste, the latter for a beacon generator that would have irradiated all life on Earth.
 * Cyclonus: As revealed in the Robots in Disguise two-part series finale, Cyclonus and his armada (consisting of Cyberwarp, Skyjack, Treadshock, and Riotgear) overthrew the High Council and disguised themselves as Autobots, brainwashed the Autobot populace into submission, tried to bury Optimus Prime's legacy, blacklisted practically every Autobot, gave Soundwave the idea of constructing a nuclear beacon generator, set Steeljaw's pack and a brainwashed Dropforge on Bumblebee's Autobot team as distractions, and ultimately planned to send an invasion force after Soundwave failed. All of this was because Cyclonus wanted Megatron back to restart the Decepticon Empire, yet was either unconvinced or unaware of Megatron's "change of spark". When he repeatedly punched Bumblebee during their battle in their combined forms Ultra Bee and Galvatronus, this proved to be his undoing as Cyberwarp turned on Cyclonys and gave Ultra Bee an opening to end his reign of terror.

Ed, Edd n Eddy

 * Eddy's Brother: Crosses the line with his sadistic and cold-hearted treatment of Eddy, gleefully admitting he has always been doing it which causes distress to the other Eds. Even Kevin, Nazz, Rolf, Sarah, Jimmy, and the Kanker Sisters are disgusted, especially when he attacks Edd for trying to defend Eddy.

Villainous

 * Black Hat: Where do we even begin?!
 * Produces weapons and monsters to be used by the various villains of the Cartoon Network Multiverse.
 * Abuses Dr. Flug, verbally and physically.
 * Scares Demencia and 5.0.5 a lot.
 * Tears an arm off of Cam-bot after it attempts to put makeup on him.
 * Ruins Christmas for everyone in town by inserting bombs in their homes.
 * Spreads the "Evil Flu" to Flug and 5.0.5.
 * Uses a size-altering ray on 5.0.5., turning him into a "monster-sized bear".
 * Savagely tears apart a malfunctioning Hatbot-Sentinel.
 * Deviously tests the Flower of Pure Foulness on Flug and Demencia.
 * Juices Lemongrab for being a terrible excuse for a villain.
 * Blows up a random planet using his signature Magisword, the Black Hat Magisword; this was done out of boredom.
 * (Possibly) kills Nohyas for being a terrible excuse for a Skinwalker.
 * Sends a Hatbot-Sentinel to torment Lord Boxman as his way of having Box More become a subsidiary of Black Hat Organization.
 * Kicking helpless animals really far to the point of having a multiversal record.
 * Uses heroes as baseball bats, to which he enjoys.
 * Zaps the Townsville narrator with his laser vision.
 * Force-strangles Flug, telling him not to get his hopes up.
 * Expresses satisfaction over Aku's death because he could forget that he ever existed.
 * Dr. Flug: Crosses it by sending Hatbots to attack Demencia every time she interrupts a Villain Orientation Video, subjecting Mojo Jojo to his experiments for becoming a disappointment amongst evil geniuses (especially since Mojo himself was the one responsible for the Powerpuff Girls' creation), subjecting Rob/Dr. Wrecker to painful brainwashing for giving up his chance to end Gumball, providing Vilgax with an alternate Omnitrix that ultimately led to his own demise, shattering Peridot for defecting to the Crystal Gems, and shattering Jasper for not being an effective villainous subordinate. These are the few moments where Flug shelves his cowardice and possesses a darker side.
 * Demencia: Crosses it when she murders Heavy Punch at the end of "Guide for an Evil Conquest".

Others

 * Mojo Jojo: In The Powerpuff Girls Movie, he fools the girls into building him a laboratory, kidnaps simians from the Townsville Zoo, releases the primates to roam free around town, and threatens to snap his former owner Professor Utonium's neck if the girls refuse to surrender.
 * Camp Bullies: In the beginning of the movie, they're just mean and petty, but when it comes to the river raft race they have been cheating stealing and destroyed the other boats leaving nobody to win but themselves.
 * Light Yagami: Betrays and kills Kiyomi Takada after she does his bidding by using a page of the Death Note to kill Mello. In the Japanese live action movies, he is even darker and crosses it when he manipulates the death note to make it look like his girlfriend Shiori was murdered by Naomi Misora to gain L's sympathy which even horrifies Ryuk who asks Light if he ever loved Shiori to which Light only responds with "I don't know."
 * Shun & Mrs. Ayasaki cross it in the first half of the first episode of Hayate the Combat Butler when they steal Hayate's hard earned money, gamble it away, and when they get into massive debt with the Yakuza, they give their own son their debt and leave him for the Yakuza without any remorse.
 * Blond Men cross the Moral Event Horizon as they turn Mordecai away from Rigby solely because he was wearing a blonde wig and Rigby was not. They also crossed it when they tried to dump Rigby in boiling hot blond hair dye.
 * Zapp Brannigan: Fakes the destruction of Earth to Leela and pretends to take care of her, all in an elaborate plan to seduce her in an Adam and Eve scenario.
 * Barry Dylan: Kills Sterling Archer's first real love Katya at their wedding and later usurps Nikolai Jakov as head of the KGB and kills Jakov under the impression that he could be Archer's biological father.
 * Fallen Hana: She definitely crossed it when absorbed and killed Hana in front of Syu. After she killed Hana in front of Syu, she used the Memes to kill him. Syu was finally killed by the CPUs after he gave up in fighting against his 'addiction" (the Memes and Fallen Hana was Syu's addiction on internet, anime, and other things that vitiate an otaku in a virtual world. The objective of the anime was to shows that not everyone win their "own addiction"). After he had finally given up the fight, she did the Memes pulled all parts of Syu's body and finally kissing and eating him along with all other Memes girls.
 * She crosses again when she devours Syu in front of Hana and made him into pieces.
 * Sterling Archer: Crosses it in "Heart of Archness Part 3" when he is willing to participate in a pirate lacrosse game rather than help his friends escape the pirates' fortress and give Ray lifesaving medical treatment.
 * Malory Archer: Crosses it by neglecting and abusing her son as a child, including leaving him at a train station on Christmas Eve and stealing his bike just to teach him a lesson.
 * The Lich: Crosses it with his plan to destroy all life. He also killed Billy and Prismo.
 * Slade: Forced Robin to be his apprentice by implanting nanobots into all of his friends' bodies. Later manipulated and influenced Terra to betray other Titans, especially Beast Boy. These are avenged when Slade gets killed in a volcanic eruption caused by Terra.
 * Mac Antfee: Cross this by selfishly left Dickie for frozen for years until Randy undo this by destank Dicky through reunite him with his long lost love. He crosses this further by tries to retake the Ninja mantle from Randy in aggressive manners until Randy stops him by mind-wiping, finally put and end of his evil nature for good.
 * The Count of Monte Cristo: The Count has had a series of Moral Event Horizons throughout the anime Gankutsuou. He has had a hand in the many misfortunes of the Villefort, Danglars and Morcerf households, causing serious collateral damage that completely unaffected the Count except for when Albert was poisoned, but this was because the Count was still using him. The character Haydee Tebelin was purposefully sent to the opera house so that she could be forced to see Fernand Mondego, the killer of her father and the one responsible for her and her dead mother's enslavement, making her have post-traumatic stress that would eventually build up until she confronted Mondego during his campaign. After the Count explained his use of Haydee and Albert, his entire scheme had essentially become one big Moral Event Horizon. Also, in the episode called "The Duel", Franz d'Epinay takes Albert de Morcerf's place in the duel against the Count and loses, dying by the Count's sword. Afterward, the Count plays chess, seemingly treating his cruel actions as if they were nothing, and when Haydee confronts the Count, Bertuccio is ordered to take her away. And in the semifinal episode "Edmond Dantes", the Count still wanted revenge even as he was dying, only somewhat affected by Albert's intervention.
 * Halloween: Punishes Ian by having Chimera turn Gido into a frozen monster. He later tries to slaughter entire audience while dueling Alan. Though, Halloween, as Pamp, actually has crosses MEH for the first time by brutally kills bullies that used to bully him by set their house ablaze (mutilate them in manga). He also mocks Alan as a hypocrite (though in reality Pamp is hypocritical) and misimpretating Alan's advice to became stronger by killing the weak one as brutal as possible (actually, Alan mean that how Pamp became stronger is not by power, but by his heart).
 * Chameleon (T.U.F.F. Puppy): He kills Agent Kitty 8 times and attempted to do it 9th time to kill her completely as cats have 9 lives.
 * Eustace Bagge: Gathers Katz, Le Quack, the Queen of the Black Puddle, the Cajun Fox, the Weremole, and the Clutching Foot to kill Courage in a deadly dodgeball game, using his own wife Muriel as bait, all out of reading the end of his rope from jealousy.
 * SwaySway: Attempted to drug, marry, and presumably rape an underage female camper.
 * Verminious Snaptrap: Pretends to be turned good by giving away muffins, clearing bad weather and opening a mall while giving away "free" frozen yogurt. But after he lured everyone into the mall he revealed that he was planning to kill everyone in Petropolis by sending them to the sun. If it had never been for Kitty and Dudley, Snaptrap would have killed hundreds of innocent civilians. This may have been a result of him "going cuckoo" during his time in prison, a shown that he was willing to kill himself along with everyone else, and that he made himself a girlfriend made of soap named Vivian.
 * Uighur: Crosses it by nearly having prisoners executed after his supposed victory over Kenshiro.
 * Kaorinite: Crosses it by nearly crushing Heart crystals of her victims and almost crushes Usagi's locket that she needs to become Sailor Moon.
 * Slagar the Cruel: In "Redwall", he loots valuables from the Redwallers after they nurse him back to health, and hits Methuselah over the head with a candlestick, killing him.
 * Queen Beryl and Queen Metallia: Caused the destruction of the Moon Kingdom, forcing Queen Serenity to sacrifice herself to temporarily imprison them.
 * Wiseman: He kills Saphir/Sapphire when he realized his evil plan and turned good, and had always intended to do so beforehand. He also tries to kill Sailor Moon resulting in Prince Dimande/Prince Diamond sacrificing himself to save her, manipulates Chibiusa/Renni into becoming Black Lady by convincing her that Usagi/Serena and the others do not care for her, and intends to destroy the world with the power of the Dark Crystal.
 * Ren Höek: In Adult Party Cartoon 's episode "Ren Seeks Help". Ren crosses the MEH, recounting how he abused other people, including Stimpy throughout their relationship, especially since childhood, he was torturing and killing tiny animals and abusing Stimpy throughout their relationship, all for fun. The psychologist Mr. Horse does not bear Ren's sadistic nature, lashes out at and challenges him to fighting. Ren turns into a rabid beast, striking the psychologist, very nearly killing him. He is taken away by animal control, but not before biting off and eating one of the men's hands.
 * King Goobot: In the movie, he steals all of the children's parents, and tries to feed them to their god Poultra. Later tries to get Poultra to eat all of Retroville, and later traded his brother Ooblar for sulfur butter.
 * Zorak: On a particular episode of Space Ghost Coast to Coast, he eats his little nephew Raymond alive and covers up Raymond's pleas for help.
 * Tetsuo Shima: He kills the barkeep then Yamagata. Tetsuo then began a rampage to find Akira as he kills soldiers.
 * Rob/Dr. Wrecker: Tried to blow up a school bus with Gumball, Darwin, their father Richard, their classmates, Principal Brown, and a few other adults, only to get undone by the explosive briefcase he ended up taking. He later tried to alter space and time using a special remote bought at the Awesome Store (according to an episode of Villainous, the remote was actually stolen from Dr. Flug and sold to the Awesome Store Manager by Black Hat) to end Gumball, yet Gumball was able to rewind time. In the rewound timeline, he does the same MEH crossing from before, yet Gumball successfully defeats him only to discover that doing so leaves him empty. These are all avenged when Rob spared Gumball, realizing that ending him will leave him just as empty, and rewound time to ultimately destroy the remote. To be honest, the cause of all these crossings is because Rob dislikes being an irrelevant background character to the Watterson family.
 * King Zenoheld not only tries to destroy the Bakugan, but once that failed, he changed his plans to destroy every living being that dare to opposed him, (including his own people). This plan has gone too far, which caused Volt and Lync to betray the Vexos.
 * Basque Grand: In the 2003 anime version of Fullmetal Alchemist (in the manga version and Brotherhood he was a hero) Grand ordered Colonel Roy Mustang to murder Winry's parents during the Civil War flashback simply because they were healing Ishvalans, classifying them as traitors.
 * Shou Tucker: In order to keep his State Alchemist license and "pursue knowledge", he experiments on his daughter Nina and the family dog Alexander, melding them into a "talking chimera". This mirrors his previous experiment two years before where he forcefully transformed his wife into a suicidal talking chimera and lied to his daughter about her disappearance.
 * Justice (Afro Samurai): Killed Afro's father before his eyes many years ago and told Afro to challenge him when he was ready.
 * Lord Akudaikan: freezes the Kiryuu twins in time and condemns their bodies to the bottom of the drink, and Goyan betrays his master, revealing himself to be the main villain.
 * Girinma: turns a memento of Urara's dead mother into a Kowaina.
 * Char Aznable: A rather complicated one for the most famous villain of the original Gundam series. Some think he crossed the line in Mobile Suit Gundam, when after finding the White Base hidden in a bombed-out stadium during a battle against the Gundam, he sees a chance to finally take revenge on the Zabi family (who were responsible for the assassination of his father "Zeon Zum Deikun"), and cunningly betrays Zeon's Earth Attack Force commander Garma Zabi, by misinforming him that the Gundam was retreating and that the White Base is directly ahead, when in fact it was actually behind them. Garma, eager to prove himself, takes the bait and as soon as his Gaw attack carrier flies over the stadium, the White Base launches a surprise attack on Garma's Gaw. Desperate, Garma attempts a kamikaze run on the White Base, while Char contacts him informing of his treachery, saying to Garma that he should blame this on the misfortune of his birth and he should thank his father, ending it with a maniacal laugh, as Garma's Gaw explodes before it could collide with the White Base. Others think that he crossed it when he decapitated Kycilia Zabi with a bazooka. However, Char (despite his delusional goals and beliefs to migrate all of mankind on Earth into space, so that all of humanity will evolve into "Newtypes", and allow the Earth to heal itself) actually crossed the line in "Mobile Suit Gundam: Char's Counterattack", when he dropped the asteroid "5th Luna", onto Lhasa, Tibet, killing billions of innocent people and attempted to complete his plan by dropping the asteroid "Axis", filled with nuclear missiles onto Earth, in order to ensure an endless nuclear winter that will render the planet uninhabitable. And he deceived and manipulated his underlings feelings with his charisma for his own ego.
 * Miss Simian: In "The Ape", it is revealed that she only pretended to be friends with the Watterstons to get a favorite teacher nomination. When teeterting over a broken bridge on her car in an attempt to reach their letter, Gumball and Darwin offer her the chance of friendship, but she declines and goes for the letter, getting herself badly injured and claiming that it was worth it.
 * Phantom Limb: When he finds out the Monarch and Dr. Girlfriend are getting married, he intimidates the Monarch by shooting his former prison mates (except for King Gorilla), some of which weren't killed instantly.
 * Floyd and Jolene: When they stole Gus' paddlecab and lured him into quicksand to drown and die while they used the paddlecab to capture some of the cubs for dinner. Naturally, as expected, their plan is foiled after Kissyfur, Beehonie, Toot, and Miss Emmy Lou all free Gus, allowing him to once again put the gators in their place and then rescue the cubs and retrieve his paddlecab.
 * Gilgamesh: While more of an anti-villain with hidden depths in other Fate titles and routes, he actually crosses the line once in Unlimited Blade Works when he rips out Ilya's heart, and again in the same route when he uses Shinji Matou as a vessel for the Holy Grail.
 * Eva-Beatrice: Crosses it with repeatedly murdering Rosa and her daughter until the original Golden Witch gives them a mercy kill. Kills the family repeatedly than just once.
 * Barrot: Often made sexual moves onto his own daughter, Phryne.
 * Frank Jones: Fails Muscle Man after his friends helped him repair his trailer, even having his henchmen destroy the architects. He later goes to extremes to take it away from Muscle Man. However, it is later revealed that Frank was a jealous contestant who lost the trailer to Muscle Man in a hot dog eating contest.
 * Raynare: Pretends to be Issei's girlfriend and then kills him, thus disobeying Azazel's orders not to hurt him. After thinking she killed him, she told her friends about how she pretended to be Issei's girlfriend and makes fun of it. She then does it again by stealing Asia's Twilight Healing, killing her in process & then told Issei that it is the deserving fate of all Sacred Gear users to have their Sacred Gear stolen by Fallen Angels in process.
 * Daffy Duck: In one The Looney Tunes Show episode "The Float", he takes every cent of Porky's money, saying he needs it for a kidney operation. After going bankrupt, Porky eventually discovers that Daffy used the money to buy a yaht and attacks him for it.
 * Red Guy: Crosses it in the episode "Part-Time Job", where he nearly cooks Chicken alive in one of his various schemes. May have crossed it even earlier in the pilot episode for the series in which he dragged Chicken to Hell and tormented him, just because he was smoking.
 * Gumball Watterson: Crosses the Moral Event Horizon in "The Saint", when he commits multiple immensely-horrific and truly evil deeds against Alan in an attempt to break his saintly goodness and cause him to fall to Gumball's level; obliterating his social life by posting a racist online message against 2D people under Alan's identity, shattering Alan's romance with Carmen by forging pictures of Alan cheating on her with everyone and everything else indiscriminately, and finally, selling Alan's parents off to be used to their suffering as children's party balloons. Gumball also, when Alan feigned Gumball finally finding his weakness and breaking him, chose to gloat and relish in his own alleged victory. Darwin Watterson was completely disgusted at Gumball choosing to do this, and Gumball nonchalantly revealed that he simply wanted to break Alan "for science, and because the people deserve to know, and because I've got nothing else to do today.". Even Gumball himself worried after selling Alan's parents that he was going too far, and Darwin said, "You went too far about seven hours ago.".
 * All the main villains in Winx Club are pure evil, but the Wizards of the Black Circle particularly proved irredeemable; Even with the critical situation they were in, with the earth fairies seeking vengeance on them and Duman seriously ill, they were faking their surrender in an elaborate plan to destroy all fairies, which they never once considered backing out of even with the Winx going out of their way to help them. Also, Gantlos, who is the most caring towards his partners, tries to kill Bloom moments after she saves his life.
 * Dark Danny: Having a ton of evil acts which began from killed his own human self.
 * Shredder (2012 TMNT): In "Annihilation Earth", he kills Hamato Yoshi/Splinter, allowing the Triceratons destroy the Earth.
 * D-Stroy: Truly cements himself as irredeemable when he:
 * Manipulates D-Structs (his brother) into joining him again.
 * Abuses a mother Dreadtrux to make her follow his (and D-Structs's) orders.
 * Attempted murder on Ty and his friends several times.
 * Becoming a horrible tyrant (with D-Structs) in the Crater, starving the residents if they don't do what they want.
 * Is more sadistic and horrible than D-Structs.
 * Attempted to betray D-Structs before his final defeat.

Super Mario Bros

 * Bowser: Forced the Toads into slavery, destroyed Peach's Castle and planned to trap the heroes inside the Paper Mario universe and destroying it by burning it, wiping out all its inhabitants as well as its heroes.
 * Dimentio: Has killed trillions and trillions of people by destroying multiple universes, and laughs about it.
 * Blumiere's father: Cursed Timpani to wander between dimensions in an attempt to thwart the union of his son and a human girl from diluting his tribe's bloodline (which destroyed his own son's innocence).
 * Mega Dragon: Fused with Bowser and knocked him to near death, brainwashing him without Bowser knowing it himself so it could destroy the Rabbits and Mario universe.

Pokémon

 * Ghetsis: Attempted to freeze (and possibly kill) the protagonist of Black/White 2.
 * Darkrai: As of his appearance in "Pokemon Mystery Dungeon: Explorers of Time/Darkness/Sky", Darkrai crosses it several times by trying to rule a world of darkness by destroying Temporal Tower to corrupt Dialga (which was later altered by the player and his/her partner) then turns the player into a Pokemon after he/she attempts to stop the destruction of Temporal Tower, imposterized his archenemy Cresselia by telling the player and partner Pokemon that they will be the cause of the destruction of space as well as manipulating Palkia about this, puts Azurill into a nightmare, and tries to kill the player, partner Pokemon, and Cresselia using several Pokemon in the Dark Crater.

Kid Icarus

 * Hades: Crosses the MEH when he tries to kill every god and become the absolute ruler of the universe.

Metroid

 * Dark Samus: Crosses the MEH multiple times, has lured and attempted murder at Samus Aran multiple times and has killed an innocent person.
 * Ridley: Killed Samus parents in front of her as a child and jokes about it, has came back multiple times to try to kill her.
 * X-Parasites: Has destroyed multiple creatures lifes including innocent people and animals.

Xenoblade

 * Mumkhar: Kills people for no reason whatsoever.
 * Zanza: Treats everyone as small little bugs and has destroyed the universe twice.

Star Fox

 * Wolf O' Donnel: While he is seen as an anti-villain, in reality, his main goal is to kill Fox, and whenever he saves him, it's only so that he can do it himself.
 * Andross: Constantly reminds Fox about how he killed his father, and has destroyed Corneria to the point that it was pretty much just a wasteland.

Kirby

 * Marx: Willingly got the Sun and Moon to fight just so that he could rule Pop Star.
 * Star Dream: Had the power to end everything, and nearly did.

Super Smash Bros.

 * Tabuu: Attempted to destroy the whole world, and whether they know it or not, the villains are working for him.
 * Primids: Slightly crosses the MEH when a fire primid attempts murder at Olimar.

Warcraft

 * Arthas: Possibly the massacre of the city of Stratholme (although this was to prevent them from falling to the Plague of Undeath and he believed it was the only option he had); definitely his cold-blooded murder of his own father, (Though technically he was corrupted by Frostmourne and is later learned in the Halls of Reflection instance that there's only a small piece of Arthas left in the Lich King which is preventing the Scourge from completely destroying Azeroth.
 * Deathwing: Used the Dragon soul to kill a large number of blue dragons, which helped drive Malygos into madness, which would make him start the Nexus War millenia later. Also responsible for the Shattering, which reshaped Azeroth and likely resulted in great loss of life. He was also attempting to complete the Hour of Twilight which would have ended life on Azeroth.
 * Archbishop Benedictus: Lead the Twilight's Hammer after Cho'gall's death and attempted to steal the Dragon Soul from Thrall, which was the only weapon that could have killed Deathwing.
 * Garrosh Hellscream: For the Alliance, Garrosh crossed this in the Jaina Proudmoore: Tides of War novel, Garrosh used a mana bomb to destroy Theramore, killing everyone except Jainna Proudmoore (though she is traumatized by the experience and warped by the residual energy of the mana bomb) and then announced a campaign of complete genocide against the Alliance. He announced that every man, woman and even child will aid in the war against the Alliance, and any who shirk their duties would face the Kor'kron guards. For the Horde, he crossed this when he attempted to assassinate Vol'Jin the leader of the Darkspear Trolls and planned genocide against the Darkspear. He finally crossed it for the Pandaren and became an enemy to all of Azeroth when he uses the sacred pools of the Vale of Eternal Blossoms to revive the Heart of Y'Shaarj to use as a weapon. His actions also destroy much of the Vale of Eternal Blossoms, filling the ground with Sha corruption and unleashing the Sha of Pride.
 * Queen Azshara: Attempted to summon Sargeras to Azeroth to become his queen and cleanse Azeroth so it would be perfect for her. Also allowed her subjects, the Night Elves to be killed as she only showed love for the Highborne. Her part in the War of the Ancients help cause the first Sundering of Azeroth.
 * Sargeras: Despite the horrific acts committed by Sargeras during the War of the Ancients, Sargeras crossed the Moral Event Horizon when he fought the Guardian of Tirisfal, Aegwynn, and possessed her unborn child, Medivh, directly destroying Medivh's innocence.

Date A Live Game Universe

 * Unknown (Date A Live): Crossed in the moment when she betrayed Maria, when he tried to bring Maria to her side saying they were sisters, Maria after falling into the trap, stab Marina Maria and laughed insanely as she showed her true personality. After this she became the true form of her and confessed her loyalty with Westcott. After that she opened the Fallen and dimensional portal that would break the physical laws of the simulator to destroy the systems of Fraxinus and destroyed all means of communication Tengu.
 * Eden: Crossed at the moment when Eden brutally betrayed its master Rinne Sonogami, when Eden used the feelings of Rinne to completely take her body and get the full power. After taking her body, the spiritual Eden used her ability to create a huge forest of branches throughout the Tengu city while maintaining Rinne imprisioned inside the garden and used her body as a source of power to kill all life in and Tengu soon all mankind.

Star Wars games

 * Darth Nihilus: Destroyed countless worlds through the Force and ended entire civilizations. Destroyed the Miraluka race and tortured his slaves and mutilated them into undead demons. Took away Visas Marr's eye sight. Started the first Jedi Purge and the Dark Wars. Betrayed Darth Traya and cut her off from the Force and exiled her from the Sith. Tricked the Onderon Separatists and their leaders, General Vaklu and Colonel Tobin into waging war on the Republic and the Onderon royalists and ended up taking away their homeworld from them and all of their soldiers.
 * Darth Traya/Kreia: Betrayed the Jedi Order and then the Sith after being exiled by the Dark Lords, used Meetra Surik as her weapon of vengeance to stop the Sith and to destroy the remaining Jedi Masters, led Darth Sion to his ultimate death and imprisoned Surik's friends.
 * Saul Karath: He betrayed the Republic and joined Darth Malak's Sith empire, he then lead military campaigns in Malak's name. One of the first bombings he led was on Telos IV, which killed Carth's wife. He also sent a bounty hunter to capture Bastila Shan and kill Darth Revan. He also tortured Carth, Revan and Bastila by electrocution.
 * Darth Malak: He ordered the destruction of planets Taris, Telos IV and Dantooine (bear in mind countless amounts of Sith troopers were stationed on Taris). He captured Bastila Shan and turned her to the dark side via torture. He also murdered a lot of Jedi and Republic civillians.
 * Darth Sion: He slaughtered entire crew of a Republic military ship. Killed Lonnah Vash and many other Jedi.
 * Darth Vitiate: he reconstructed Sith Empire after the Great Hyperspace War and went on to rule it for more than a millennium due to absorbing life energy from others to extend his lifespan, he ordered war against the Republic, causing death of millions, he tortured and personally killed many of slaves and jedi and tried to eliminate all life in the galaxy. *Darth Jadus: Faked his death to plot against the Sith Empire, he constructed superweapon Eradicator and attempted to start his rule of fear and terror.
 * Skavak: Backstabbed Corso and his captain, stole their starship with all cargo on the board to deliver it to separatist movement in the Republic.
 * Darth Zash: She took over bodies of her previous students and tried to do this with Darth Nox.
 * Darth Thanaton: He tried to eliminate and incriminate Darth Nox as student of his most powerful political rival Darth Zash.
 * Darth Baras: He tortured a Republic Soldier and destroyed his mind to just gain informations, he betrayed his student the Emperor's Wrath and pretended the Emperor's Voice.
 * Tarro Blood: He ordered to kill the Great Hunt Champion's friend to eliminate him from the Great Hunt.
 * Jedi Master Jun Seros: he had slaughtered the Great Hunt Champions and framed the Great Hunt Champion for a kilometer-long list of atrocities that the bounty hunter did not do.
 * Darth Tormen: He sent bounty hunter, the Great Hunt Champion, to kill or capture Zale Barrows on Belsavis and General Thelonia Redrish on Voss oficials on Corellia and Supreme Chancellor Dorian Janarus. Tormen executed the surviving bridge crew of a Republic Ship. The worst of what he did was conquering Corellia.
 * Galen Marek: For order of his master Darth Vader, he killed 3 Jedi knights. He optionally can become Darth Sidious' servant, who kills Obi Wan Kenobi and corrupts Luke Skywalker (although this is not considered canon).
 * Jerec: He killed jedi master Qu Rahn, later he killed Morgan Katarn to take his map to Valley of the Jedi, he tried to corrupt Kyle Katarn by offering him to kill his beloved and even in the very end he tried to provoke Katarn to kill him and make him turn on the dark side after the first offer failed.
 * Desann: He killed a padawan called Coulage in anger, becoming a dark jedi and lead another military campaign against Luke Skywalker's jedi order, he tricked Kyle Katarn to show him way to Valley of the Jedi by making him believe he killed his beloved Jen Ors.

Tekken

 * Heihachi Mishima: Prior to the events of the first Tekken game, he threw own his son off a cliff for being "too weak" as well as trying to kill his grandson in Tekken 3, making him responsible for making both of them much greater evils than even him.
 * Kazuya Mishima: By the time of the second tournament, Kazuya has been the Mishima Zaibatsu's CEO for two years and engaged in much more evil actions beyond that of Heihachi Mishima, though this was due to the Devil gene in his blood (though he later chose to accept it).
 * Jin Kazama: Obviously started a war in Tekken 6 to lure Azazel as a way to get rid of the Devil Gene in his blood as well his father and grandfather. After his fight with Azazel, it was revealed that his plans of ridding the devil gene failed because the mark was still on him after he was found by Raven. Due his actions in Tekken 6 and his absolute hatred for the Mishima bloodline, Jin unknowlingly became the very thing he so greatly despised.

Assassin's Creed

 * Al Mualim: He manipulated Altair to eliminate his former allies, so he would never have to share power and influence with them.
 * Rodrigo Borgia: although the deed was done by Uberto Alberti he was truly responsible for the death of Ezio's father and brothers.
 * Cesare Borgia: Cesare crossed the Moral Event Horizon when, in a rage, he murdered his father, Rodrigo, and physically abused his sister, Lucrezia, to the point of choking her, just to determine the location of the Apple of Eden.
 * Charles Lee: crosses it when he tries to break Connor's neck when Connor was a child, this leads Connor to believe that he burnt his village when it was actually George Washington. He later lies to Kanen'tó:kon telling him that Connor betrayed his own kind, which forces Connor to kill his friend.
 * Bartholomew Roberts: after showing Edward Kenway the observatory he betrays him and leaves him to die, once Edward finds a way out of the chamber Roberts turns him in for the high bounty on his head.
 * Warren Vidic: He abducts William Miles and threatens to kill him if Desmond does not hand over the Apple of Eden.
 * Shay Cormac: With no remorse, he killed Arno's father. He also betrayed the assassins over an accident and hypocritically helped the Templars hunt them down knowing they could have malicious intentions with the artifacts they sought.

Witcher

 * Azar Javed: He ambushed Kaer Mohren, stole witcher secrets, organised a criminal group Salamandra from smaller groups to gain resources for his experiments, to those group belonged slavers, drug dealers, hired murderers, kidnappers of children, which were later lab rats, he personally killed a detective to take his identity, he manipulated Geralt of Rivia to find an ancient magical book for him, he sent army of mutants on Vizima and sent murderers and monsters on Geralt.
 * The Professor (Witcher): He is a felon wanted in 3 kingdoms, he assists Azar Javed in ambush Kaer Mohren, steals witcher secrets, kills witcher Leo by his crossbow, he mocks Geralt of Rivia about his status in society and supervises many activities of criminal organisation Salamandra.
 * Jacques de Aldersberg: He's behind Azar Javed and all his acitivities, but his worst crime is provoking a rise of non-humans to crush it and make himself a hero and usurp rule of Temeria, all he did because of his delusional vision of a madman.
 * Letho: He assassinated kings Demavend and Foltest, framing Geralt of Rivia in the latter crime, he manipulated elves and sorceresses to help him kill them, he kidnapped Triss Merrigold to teleport him and left her on fate of trolls, he made a plan to assassinate king Henselt and sent his 2 coulages to kill him, in the end of the game it's revelated he was working for the emperor of Nilfgaard.
 * Serrit and Egan: attempt to assassinate king Henselt, killing all who stand in their way - soldiers and messengers.
 * Sheala de Tancarville: She hired Letho to kill king Demavend and sent a brainwashed dragon on soldiers, when they tried to arrest her for regicide.
 * Philippa Eilhart: She lead a conspiracy to kill king Demavend, she manipulated Saskia and Geralt and brainwashing the former after curing her from a poison. When Geralt asked her, what would have she do if Saskia did not get poisoned and he didn't appear to naively help her, she answered that she would find another way to take control over her mind.
 * Dethmold: He convinced King Henselt to kill Blue Stripes and orders mercenaries to kill their leader Vernon Roche and his companion Geralt of Rivia, later he captures Anais La Valette.
 * Bernard Loredo: He kidnapped and sexually abused an elven woman for a year. He can also optionally take elven women as hostages and threat to burn them alive and even commit a state treason by selling his outpost to kingdom of Kaedven.
 * Wild Hunt: For ages they kidnap various people from age 10 to 20 and turn them into their kind, they leave destruction and death behind them.

God of War

 * Ares: Tricked Kratos into killing his own family which eventually led to Ares' downfall at the hands of Kratos.
 * Zeus: Crosses it in God of War II when he tricks Kratos into draining all of his godly energy into the blade of Olympus and then uses it to kill Kratos.
 * Kratos: Despite being a protagonist and a tragic character, he destroys all he touches and revenge was so important to him, that he betrayed his allies who wanted to kill Zeus instead of letting him do that. He also caused a total chaos on whole world by killing all gods and didn't care about it. He said he wanted to kill Zeus to prevent him from killing Spartans, but that's a hypocrisy, because by slaughtering Poseidon, he drowned them all.
 * In spite of this, the events of 2018 game revealed that Kratos still have redeeming qualities. In fact, after restored by the power of hope he released to the world and sired another child, Kratos decided to turn over a new leaf: He now wholeheartly accepted responsibility from his MEH crossing acts, understanding that vengeance not bring him and others peace, and as father, ensuring his dark history not repeated in his son Atreus' life.
 * Baldr: Attempted to kill his mother Freya in revenge of making him invulnerable and refused to understand why she did so, even after Kratos and Atreus spared him and reasoned with him in their final battle. In fact, he was consumed by vengeance that Kratos, who knew better than vengeance won't bring anyone peace, forced to step in and reluctantly put Baldr out of his misery.

Mass Effect

 * Saren Arterius: Crosses it in the book Mass Effect: Revelation when he destroys a Batarian refinery, killing hundreds of civilians, and then attempts to frame Anderson for it. In the main game, he allies himself with the Reapers and manipulates the Geth, murders his colleague Nihlus Kryik, tries to blow up the colony of Eden Prime, sponsors production of Rachni troops, leaves the colony on Zhu's Hope at the mercy of a Torian, tries to produce an army of Krogan slaves and helps Sovereign attack the Citadel.
 * Ka'hairal Balak: Crosses it when he attacks a populated asteroid and installs engines to direct the asteroid at the populated planet of Terra Nova. He then tries to take people off the asteroid as slaves, kills the brother of Kate Bowman for calling for help and threatens Shepard that he'll slaughter the hostages if the commander chases him.
 * Collectors: Kidnap tens of thousands of colonists and turn them into either husks or fuel for the Human-Reaper Larva.
 * Reapers: Invade all planets and commit mass genocide on their populations.
 * Illusive Man: Crosses it when he decides to take over the Reapers at the cost of his own humanity, rather than making mankind the dominant race.
 * Donnel Udina: Crosses it when he betrays the Council and the Systems Alliance by revealing himself to be a Cerberus mole and staging a coup d'etat.
 * Henry Lawson: Crosses it by turning innocent refugees into husks or experiments. He also threatens to kill his own daughters Oriana and Miranda.
 * Zaeed Massani: Crosses it when he blows up a refinery in an attempt to kill Vido Santiago, putting the lives of countless workers in danger.
 * Tela Vasir: Crosses it when she goes rogue and tries to murder Liara T'Soni.
 * The Shadow Broker: Crosses it when he allies himself with the Collectors, tries to take Shepard's body for himself, captures Feron and tortures him for 2 years and sends Tela Vasir to kill Liara T'Soni.
 * Kai Leng: Crosses it when he attempts to assassinate the Salarian Councilor, instead killing Thane Krios when he tries to intervene. He also kills a group of asari scientists and tricks Shepard into unlocking an ancient Prothean VI before stealing it, leaving Shepard to die and allowing Thessia to be overrun by the Reapers.
 * Clan Chief Weyrloc Guld: Crosses it when he sacrifices his own tribesmen to find a cure for the genophage with Maelon Helprom's help, so he could conquer the galaxy in a bloody war.
 * Maelon Helprom: Crosses it when he conducts a series of brutal and barbaric experiments on prisoners and krogans to find a cure for the genophage. He's a well-intentioned extremist, but he imprisoned, tortured, experimented on and killed many test subjects.
 * Rasa: Crosses it when she kills Agent Brooks by shooting her in the back. She goes on to betray Cerberus and orchestrates a conspiracy to kill Commander Shepard.
 * Shepard's Clone: Crosses it when they try to kill the real Shepard so that they can steal their identity and take over the Normandy
 * Renegade Shepard: Although they have committed a number of despicable atrocities over the first two games, most fans agree that Renegade Shepard crosses it when they sabotage the cure to the genophage, condemning the Krogan race to extinction, also killing Mordin Solus to shut him up. When confronted by Wrex (if Wrex survived the Battle of Virmire) over the betrayal, Shepard can outright lie to Wrex, resulting in Shepard sadistically killing Wrex and then concealing the truth from both C-Sec and Garrus Vakarian.

Dragon Age

 * Bhelen Aeducan: Convinces his older sibling (protagonist of the game) to kill much older brother Trian, so he could be the only successor of the dwarven throne. If he fails to convince his sibling, then he simply hires an assassin to kill him and frame the protagonist.
 * Urthemiel: he unleashed horde of Darkspawn to conquer, taint and devastate Ferelden, destroying majority of the nation.
 * Rednon Howe: A treacherous and power hungry tyrant, who killed human noble protagonist's family including his best friend's young grandson and helpless daughter-in-law, out of nothing more than ambition of taking their land and framed them into treason, he also sold people of another protagonist to slavery. After all protagonists he sends a band of assassins.
 * Loghain Mac Tir: Leaves his king to die on battlefield and takes over his kingdom, hunting and executing all his political enemies, including sending a maleficar to poison Arl Eamon, sending assassins after the protagonist, selling elves to slavery.
 * Uldred: He summons demons and starts a revolt on mage tower with his fellow blood mages. He also turned most of mages into monsters possessed by demons and enslaved them and some templars to fight for him.
 * Paragon Branka:  Does not so much cross the horizon as she flies across it, laughing the whole way. We find out just how completely depraved and insane Branka is when it is revealed that in order to reach the Anvil of the Void, she sacrificed her house — three hundred plus dwarves — to the Darkspawn and allowed the women to be taken to become part of the Broodmother (a process that defines horror) just so she could have Darkspawn to throw at the traps surrounding the Anvil. The sole survivor, Hespith, explains it in simple terms: Hespith: But the true abomination... is not that it occurred, but that it was allowed. Branka... my love... The Stone has punished me, dream friend. I am dying of something worse than death... Betrayal. *The stories of Flemeth indicate she became irredeemable when she started to take over bodies of her daughters to extend her existence.
 * Marjolaine: Crosses it in the DLC Leliana's Song where the player gets to see Marjolaine's betrayal of her friend/lover firsthand. When Leliana discovers Marjolaine has been committing treason against Orlais, she confronts her about it, not because she's angry at what Marjolaine's done, but because she fears for Marjolaine's safety. Marjolaine responds later on by knifing Leliana in the gut, hands her over to Captain Raleigh to be tortured, and strongly implied to be raped, and alters the document so that Orlais believes Leliana is the traitor.
 * Quentin not only killed a lot of women, but also disrespected their corpses by chopping them and turning them into a twisted attempt to recreate his dead wife.
 * Anders crosses the line when he blows up the Kirkwall Chantry, killing the Grand Cleric and presumably all of its priests in order to destroy any chance of compromise between the Circle and the Templars as the Grand Cleric was the only one who could calm both sides down. He willingly started a war, even Orsino scolded him for this, because he may have doomed their whole kind, or at least the mages who live in Kirkwall.
 * Then Knight Commander Meredith Stannard followed him when she used it as an excuse to annul (exterminate) a Circle of Magi that Anders never even belonged to and were not involved in his crimes. However if player takes her side, she can be persuaded to spare mages, who beg for mercy, including player's sister Bethany.
 * Then Orsino crosses it when he reveals that he knew about and protected the Serial Killer blood mage Quentin. While he downplays his crime in the Mage path, he is wholly unrepentant in the Templar path about being complicit in the deaths of several innocent women, including Hawke's mother Leandra. He even uses the fruits of Quentin's research to turn himself into a literal monster after the reveal. *Mother Petrice crosses it when she murders Seamus Dumas, tries to frame Hawke for it, and plans on using the entire affair to incite the citizens of Kirkwall to rise up and wage war against the Qunari. Her apathy towards Hawke pointing out how it will be a massacre on both sides of the conflict further solidifies just how much of a deranged zealot she really is.
 * Arishok: Provoked by Petrice and other xenophobes he began a war against Kirkwall, his soldiers massacred many citizens, when he personally decapitated viscount Dumar and throwed his head to intimidate citizens to make them submit.
 * Isabela: She could have return a qunari relic to Arishok and prevent a war with him, but instead she escaped. Many years earlier she drowned slaves imprisoned on her ship, so she wouldn't have a trail for slavedriving.
 * Bartrand Tethras: He sealed his younger brother Varric with Hawke and 2 other companions in an ancient underground temple and left them to die, so he would share profits with them.
 * The Architect: He started the Fifth Blight, but decades earlier he tried to spread the darkspawn taint on the whole world, knowing that most of sentient beings will die.
 * The Mother: She ordered her darkspawn to kill the protagonist and ambush city of Amarantine and Vigil's Keep forcing the protagonist to choose one of the locations to protect and leaving the another at the mercy of Darkspawn.
 * Varania: She made a deal with Danarius to trick and capture her own brother Fenris to become Danarius' student and a magister, an influential wizard noble.
 * Danarius: he sent his servants and bounty hunters after Fenris. If he captures him, then he ereases his memory again.
 * Corypheus: He crossed MEH, when it was revealed he opened the Breach and killed Divine Justinia V as a sacrifice for the ritual. 12 centuries earlier he sacrificed thousands of slaves to enter the Golden City and take it over, but he became a taint spreading monster and started the very First Blight. He continued crossing MEH by turning templars into his monstrous slaves, brainwashed rebel mages by Venatori, brainwashing grey wardens himself, attacking Haven and sending an assassin to kill Emperess Celine.

Resident Evil

 * Albert Wesker: Betrayed S.T.A.R.S after it was revealed that he really worked for the Umbrella Corperation. He threatened to harm Barry Burton's family if he didn't follow Wesker's orders. Kills Ozwell Edward Spencer, the founder of Umbrella, so that he could have the "right to become a god" all to himself. Kidnaps Jill Valentines and brainwashes her to work for him. Betrays his partner, Excella Gionne, after infecting her with the Uroboros Virus which turned out not in condition that suits her DNA, and eventually transformed into a gigantic monster, despite all she's done for him. Albert would then plan to spread Uroboros all over the Earth, possibly killing every human and even destroying the entire planet. He kept denying that he was destroying the Earth, he kept claiming that he was "saving it".
 * Brian Irons: After he realizes that the T-Virus is destroying Raccoon City, he decides to take the opportunity to do whatever he wants, even kill his own fellow police officers. He also kills the mayor's daughter so that he can turn her into his personal trophy.
 * Osmund Saddler: Transforms an entire village of innocent farmers into bloodthirsty savages as well as loyal followers for the Los Illuminados cult with Las Plagas.
 * Derek C. Simmons: Infects an entire town with the C-Virus, turning them all into zombies and those who were never infected were killed brutally killed by the zombies. Among the infected was the Adam Benford, the President of the United States, which Leon had no other choice but to kill. Simmons had also kidnapped Helena's sister, infected her with the virus, and mutated her. He even relentlessly tries to kill Leon and Helena while fighting them with power that he gained from C-Virus infection caused by Carla. Worse, Derek also reveal his genuine disgust toward Sherry' cheerful attitude before the fight began (hinting that he genuinely hate Sherry and he sees her as his mere tool for creating C-Virus with Jake all along).
 * Carla Radames: Tricks the Edonian Liberation Army into using "energy boosters" (in reality, it was the C-Virus) turning them into J'avo, imposterized Ada Wong and destroyed her good name, turns most of Chris Redfield's BSAA troops into J'avo, spreads her creation into Lanshiang, China & attempts to infect the entire world.

Tales Series

 * Van Grants: Manipulated Luke Von Fabre into destroying Akseriuth, thus causing every civilian to die and having Luke (briefly) losing all respect from his friends. The worst part however, was due to the situation, the group even had to watch an innocent little boy die by drowning in the bottomless mud of miasma.
 * Emeraude: Although a minor villainess, Emeraude was considered the true cause of Lambda's evil and the Little Queen's birth. She had him put through several experiments, tried to have him destroyed when he caused chaos around the humanoid research center (though unintentionally, cause he was young and innocent), and had her humanoids kill Director Cornell. It was then that she decided to create Protos Heis/Sophie in order to help rid Fodra (later Ephinea) of Lambda. Of course at Lambda's Cocoon, Emeraude becomes a hypocrite by zapping Sophie to keep her from vaporizing the empowered Lambda and decides to hoard his power (which came from the 3 Valkines) for herself, thus declaring herself a "goddess".
 * Rodyle: Tries to drown an entire human ranch with seawater after being defeated in battle just to kill Lloyd's group and all the prisoners.

AdventureQuest

 * Drakonnan: Mind-controls the hero into destroying a random town, and later kills Demento.
 * Sepulchure: He loses a lot of sympathy when he crashes Shadowfall into the Guardian Tower in Falconreach, causing massive destruction and resulting in the deaths of so many good men and women. He also arranges for Lady Celestia's death at the hands of Xan and an Akriloth, turned into Akrilich at the time.
 * Ledgermayne: Just when the hero is about to accept the Chaos Focus Gem into the Supreme Arcane Staff, Ledgermayne crosses the line when it snatches the gem and shatters it into several pieces in front of him/her.
 * Vordred: As if turning several paladins undead until only Artix is left wasn't evil enough, he goes even further when he turns the hero undead as well.
 * Exos: When Lithos stopped him from murdering Stratos, he killed Lithos in response. He also murdered Terra by pushing her off a cliff into the ocean below.
 * Maximillian Lionfang: In the Thunderforge saga, he begins torturing the staff of Artix Entertainment in an attempt to get them to accept his way of doing things, and later wastes the last vial of the Tears of the Mother on Drakath, and when he finds out that it didn't effect him, he goes so far as to try to murder the hero due to being sick of what he believes to be his/her tricks and lies. In the 2010 Frostval event, he burns the Frostval gifts in front of Blizzy to his horror and laughs about it, which sends the hero into a ballistic rage with the promise of making him pay for it. Not long after his defeat following that, he, in one more act of spite against the alliance between good and evil, knocks the snow globe containing the Frostval Spirit out of the hero's hands and shatters it, and lays bare his intent to make the whole world pay for "pledging allegiance to evil" by destroying Frostval, but the Frostval Spirit cannot be destroyed, as she returns to his shock and disbelief in order to set things right again.
 * Drakath: While the siege of Swordhaven by Drakath's forces is pretty standard villain fare by this point, and chaorrupting Swordhaven's sewers is a new level of low, everything takes a turn for the worse when King Alteon finally succumbs to the Chaorruption he's been having to deal with all game thanks to Drakath's first appearance, becoming the 12th Lord of Chaos and striking down his eldest daughter and heiress to the throne, Princess Brittany, in a fit of Chaos-induced madness — and right when she had just gotten married to Lord Brentan! And to make things even worse, this tragic act happens to be the trigger for unleashing the worst Chaos Beast yet: a massive, three-headed Chaos Dragon who unleashes horrific devastation upon Swordhaven before the hero is able to take it down, and King Alteon himself ultimately has to be slain when the Chaos proves too much for him. Because of all of this, Swordhaven will never be the same again, and will most likely never know peace for a long time due to the inevitable conflict for the throne. And from Drakath's smile as the twelfth seal is broken, players can just tell that he's enjoying the whole show. Later, after besting the hero in battle, he chaorrupts him/her into the 13th Lord of Chaos and gleefully watches his final, world-ending Chaos Lord wreak havoc in Willow Creek, Doomwood, Darkovia, Vasalkar Lair and Battleon and summon his/her Chaos Beast, the Eternal Dragon of Time. After being attacked by the hero and revealing him/her to be the Dragon of Time, he then murders him/her and then crushes his/her soul within his hand and controls Death into preventing him/her from respawning like normal, which allows him to free the Queen of All Monsters.

inFamous

 * Kessler: Strings Trish on one rooftop and six doctors on the other, forcing Cole to choose between the love of his life, or the lives of thousands more people. If Cole chooses to save Trish, it is revealed Trish was one of the six doctors (this does not happen if Cole chooses to rescue the doctors). Either way, Trish dies, and Cole swears revenge on Kessler over his former girlfriend's grave. Ironically, he was subverted in this MEH crossing deed, as he crossed it in order to made Cole prepared enough to face the larger threat. However, if this deed is not enough, he still crossing it by having Alden Tate left into the street to die soon after usurp the First Sons organization from his family.
 * Joseph Bertrand III: Tricks a group of people (includes young Nix) somewhere to kill them with a Ray Sphere which in turn bestows his powers in process. Ironically, this only causes him bestowed an uncontrollable monstrous powers instead superpowers like both his nemesis Cole and adult Nix instead. He crosses it again by attempting to create a war between Conduits an normal humans so Conduits will be eradicated from face of the earth.
 * Kuo: She potentially crosses it in the good ending when she tries to kill Cole and Nix to prevent them from charging the RFI, a device that absorbs the powers of Conduits world-wide, and kills them, and also cures a plague that is killing thousand, just so she could live. Arguably, she redeemed herself when she showed up just before Cole activates the RFI, and apologizes, saying she was wrong and Cole was right, and "hell, even Nyx made the right decision.".
 * Brooke Augustine: Kills Reggie Rowe, Delsin's brother by encasing his feet in concrete, even after Delsin told her to let him go. This prompts Reggie to commit heroic sacrifice by let himself fall to his death to prevent Delsin engulfed by concrete along with him. She shows no remorse afterwards, even after Delsin angrily attacked her and screamed at her. She also beat Delsin into near death as well until Delsin fought back by absorb her power. **This was not sole reason to hate her, however. In fact, the consequence of Augustine's plans would be a war between conduit and humans, something which dreamed by Joseph Bertrand III in the past. Worse, her evil actions proved be more active and more aggressive manner than Bertrand ever did; Hunt every single conduit gene possessors and lock them as well as infect whole Akomish Tribe's body with concrete that slowly kills them. Nevertheless, all of her actions are what was drove Delsin to kill/stop her at all costs from start (incarcerated her in Good Karma/destroyed in Evil Karma).

Grand Theft Auto

 * Claude Speed: Crosses it several times by secretly working for all gangs in Anywhere City, betraying their bosses and then killing them all.
 * Trevor Phillips: Although he is a protagonist, pretty much anything he does throughout the game can be considered a moral event horizon, but he especially crossed it when he allows Michael De Santa to be abducted by Wei Cheng, when he finds out that Michael was responsible for Brad's death.
 * Michael De Santa: Crosses it when he fakes his death, leaving Trevor and Brad to die (although Trevor survived, while Brad died).
 * Devin Weston: Crosses it when he sends a squad of Merryweather mercenaries onto the DeSanta family when Michael accidentally causes the death of his lawyer Molly, even though Devin didn't care about about Molly as a person as much as an asset.
 * Steve Haines: Shows he is sadistic when he has Trevor torture an obviously innocent man to get information on a terror suspect even when said man was willing to tell them anything. He also crosses it when he betrayed Michael and Dave Norton to cover up his tracks from the FIB raid.
 * Tommy Vercetti: Crosses it when he goes eliminating everyone and creating chaos around Vice City just so he could please Mitch Baker, the leader of the bikers.
 * Catalina: Tortures her boyfriend Carl Johnson, and randomly kills innocent people during thier bank heists. Nine years later, she shoots her new boyfriend Claude and leaves him to die, before killing her next boyfriend Miguel, using drugged suicide bombers to try to kill Claude, and abducting Maria to lure Claude into a trap.
 * Frank Tenpenny: When he was under investigation for various crimes including supporting the Ballas gang and rape, he instigated the attempted murder of Carl Johnson's brother Sweet, that leads to their mothers death. He also has his protege kill a police officer who was investigating him, and uses said death to blackmail Carl into destroying evidence, kill witnesses to his crimes, and kill those investigating him. He attempts to kill people who work for him when they are useless to him.
 * Dimitri Rascalov: After having Niko Bellic kill his boss and best friend, Dimitri summons Ray Bulgarin into Liberty City to kill Niko, and later has Roman Bellic kidnapped. In the Deal ending he sends a hitman to Roman's wedding to kill Niko, taunts Niko about Roman's death, and kills Jimmy Pegorino so they wouldn't have to share any money.

Saints Row

 * Zinyak: Has been abducting people for years as part of his collection and uses simulations to torment people and break them (each simulation is based on the subject's worst fears). He then destroys Earth just to spite the Saints.
 * Cyrus Temple: Sides with terrorists and attempts to nuke Washington D.C. simply because he couldn't handle the Saints being hailed as heroes.
 * Killbane: Breaks Kiki DeWynter's neck simply because they failed an attempt to kill the Saints.
 * The Protagonist: Tricking Maero into killing his girlfriend Jessica, although it was retaltation for Jessica having Carlos killed in her own crossing.
 * Julius Little: Tries to blow The Protagonist up on a boat, which puts them in a coma.
 * Dane Vogel: Manipulates the Protagonist into killing the Ultor Board of Directors, so that he can usurp them.
 * Richard Hughes: Has the Saints blackmailed into killing his political opponent so that he can win the mayoral election of Stillwater.
 * Kia: Abducts Shaundi, Viola and Burt Reynolds so she can kill them and frame the Saints for terrorism.

Batman: Arkhamverse series

 * The Joker: There is no denying that Joker was pure evil. Even before the events of the games he brutally tortured Jason Todd for a year and presumably murdered him (said murder turned out failed as he unknowingly turned him into the Arkham Knight instead, whom goes on hellbent to get revenge on Batman). He killed multiple people without a second hesitation in Origins, Asylum, and City, and has poisoned Gotham twice.
 * Scarecrow: He detonated the Cloudburst in Gotham City, murdering thousands, and prepared to kill Barbara Gordon for the entertainment.
 * Hugo Strange: Activated Protocol 10 in Arkham City, killing thousands.
 * The Arkham Knight: Began a civil war in Gotham City so he could get revenge on Batman.
 * Harley Quinn: Kidnapped doctors all over Gotham City to fix the Joker and when they failed she had them tortured and killed.
 * Ra's al Ghul: Was prepared to kill his own daughter in order to goad Batman into taking his place as the Head of the Demon.
 * Bane: Killed the Joker's men while he was in an alliance with the Joker and manipulated Batman to find his TITAN containers across Arkham City.
 * Penguin: Removed the eyes of a man who lodged a bottle in his eye and then had him run across the Gotham freeway.
 * Killer Croc: Killed and ate his abusive aunt.
 * Poison Ivy: Betrayed humanity by unleashing spores across Gotham City.
 * Victor Zsasz: Killed dozens of people for no reason other than collecting more marks (tally marks he cut over his body).
 * Two-Face: Despite being a sympathetic villain he refused the help of Hugo Strange and continued being Two-Face.
 * Hush: Killed his father.

Five Night At Freddy's

 * William Afton/The Killer/Purple Guy: He crosses it that he killed children and stuffed them into Freddy Fazbear, Chica, Bonnie the Bunny, Foxy the Fox & Golden Freddy. Other than that he has also murdered even more children (the Crying Child & The Children in the Foxy minigame.).
 * Big Brother: Kills his little brother at Bear Fredbear which it was happened of the Bite of '87, and possibly kick-started the Killer to commit his own crossing.

Others

 * Judge Margaret Holloway: Murdered her own second-born daughter Nora by suffocation part of the 4 Sheperd's Glen founding families' ritualistic pact with The Order's God in order to protect the local community from suffering the similar fate as the ghost town of Silent Hill. She went on to order Curtis Ackers to execute her eldest daughter Ella as punishment for her disobedience before she later died in unsuccessfully attempting to sacrifice Alex Shepherd herself.
 * Swan (Lollipop Chainsaw): Cracks open Rotten World and releases contagious gas to kill everyone and reanimate them.
 * Sephiroth: Crosses it when he murders Aerith, a playable party member and one of Cloud’s dearest friends; the most (in)famous character death in videogame history.
 * Edgar Ross: Kills John Marston, betraying him so he could take credit for killing the other gang members.
 * Nacho Contreras: In "Scarface: The World Is Yours". It is known that in addition to having dedicated to drug trafficking, was also devoted to human trafficking. It also emerged that raped and abused with womens and then threw their bodies into the sea (ironically he died at sea eaten by a shark).
 * General Shepherd: Shoots Gary "Roach" Sanderson and Simon "Ghost" Riley and kills them by having his men set them on fire. He then attempts to kill both John Price and John "Soap" MacTavish.
 * Jonathan Irons: Crosses it when he kills the technologist that was rescued in Nigeria, proving that he deliberately allowed the KVA to commence a global attack to improve the reputation of Atlas Corporation, which killed 50,000 civilians. He later declares war on the entire world, starting with the United States, using the WMD Manticore. He goes even further when he beats up Jack Mitchell in the Atlas prison camp, shoots Cormack in the stomach, and allows Gideon and Ilona to be beaten to a pulp as well.
 * Luca Blight: In the very beginning of the game, he crossed the MEH when he orchestrated the massacre of the Unicorn Brigade, youth soldier group made of children of Highland, his own country, by having his men dress up as City-States soldier in order to pin the blame to the City-States and eventually start his war. Another famous one would be the massacre at Ryube village where in particular, Luca pretended he would spare one villager if she acted like a pig. When she did so, he delightfully killed her anyway while yelling, "DIE, PIG!!!!!!".
 * Mad Doctor: Lied to Oswald about being redeemed, made Prescott turn on his friends, and kidnaps all the Guardians which would kill everyone.
 * Shadow Blot: Threatened to kill Oswald and Gus unless Mickey gave him his heart.
 * Dr. Nefarious: He set his ship, the Leviathan to self-destruct to kill Qwark (except Ratchet, Klunk, and Skrunch who escaped) and set his super weapon known as Biobliterator to destroy Metropolis and turn everyone into robots. He later supposedly killed Orvus, Clank's father, on Zanifar, after him telling Nefarious that the clock is not a time machine.
 * Neftin and Vendra Prog. After Neftin rescued his sister, they set the bombs to destroy the prison ship where Cronk and Zephyr were killed except Ratchet and Clank who escaped. But, They turned themselves in after the Nethers are back in their universe.
 * Percival Tachyon: Tachyon raided the Lombaxes after his creation was complete, and after that Tachyon confronted Kaden and killed him for refusing the location of Ratchet and when he got the item called the Dimensionator, thanks to Qwark, He finally brought his race called the Cragmites to come back and invaded Igliak and Fastoon before the final battle with Ratchet and Clank. He also enslaved an entire galaxy.
 * Kefka Palazzo: He crosses the MEH when he poisons the entire kingdom of Doma, completely disregarding the orders of General Leo as well as basic war conventions, and later shifts the Warring Triad, resulting in the ruination of the world and the deaths of many.
 * Shao Kahn: Crosses it when he dishonorably and brutally snaps Kung Lao's neck while his back is turned at Shao Kahn's Coliseum.
 * Iris Sepperin: Manipulates all of RKS into fighting against the Holy Empire and Orthodox Church for her own amusement, has her father imprison Karl for attempting to kill her because he saw through her facade, kills her own father because she no longer needs him in her plans, and later brainwashes Spiritia into fighting against her own childhood friend Freudia.
 * Mephiles the Dark: Crosses it when he kills Sonic in order to make Princess Elise shed a tear, thus releasing the trapped essence of Iblis, whom Mephiles merges with into Solaris, whose sole purpose is to consume all existence.
 * Aparoid Queen: She is the darkest villain in the Star Fox series, trying to assimilate all life in the universe, but she crosses the Moral Event Horizon when she sends an army to attack Sauria, killing the ThornTails that Fox worked so hard to protect in the previous game, and presumably many other dinosaurs as well. She also begins to assimilate General Pepper, forcing him to fight Fox, who is forced to almost kill Pepper. Peppy and Star Wolf nearly sacrifice themselves to enable her destruction as well.
 * The Darkness (The Darkness): Ensnares Jackie Estacado and prevents him from saving his girlfriend Jenny's life just to establish its dominance over him.
 * High Councillor Superman (Injustice: Gods Among Us): Murdered Shazam after the latter tried to talk him out of destroying Metropolis and Gotham City.
 * Gruntilda: In Banjo-Tooie, she kills Bottles and zombified King Jingaling, attempted to use his life force and planned to blast the entire island to help bring back her original body.
 * Comrade Black: In De Blob, he took over Planet Raydia with brute force and forced all its inhabitants into slavery just to expand his INKT corporation. In De Blob 2, he used deceit by disguising himself as a benevolent priest, rigged the voting for Prisma City's new president, and then again forced the Raydians into slavery. Also, while Blob was restoring color to the planet, he ended up using Blob to obtain color energy to power a giant satellite that would hypnotize the entire planet, once again using deceit as his weapon, implying that in De Blob 2, he turns to a new, darker level of evil.
 * Count Vegar: May have crossed it when he banished Jak to the desert. But he really crossed it when he did not tell Jak that his father was Damas, who died that moment. It's revealed that he took Jak from Damas. When Damas died, he rhetorically asked Jak if he told him too late, and said it was wonderful he never knew.
 * Crow (Guilty Gear): Has done several unforgiving things in the story mode of Guilty Gear Accent Core Plus. In Dizzy's story mode in the good ending path, he tries to kidnap her & even scares her by bring a clone of Justice to fight her while in the bad ending, he successfully kidnaps Dizzy with a help from A.B.A. whom he blackmailed and then starts experimenting her. In Johnny's story mode, Johnny considers him a traitor to the Japanese people in which he villainously rejects. In both Johnny's story mode as well as May's, he admits about May's origins being Japanese much to her curiosity and Johnny's anger which he considers nothing but useless trash. In A.B.A.'s bad ending, he blackmails her into kidnapping Dizzy & when the latter escapes thus placing Paracelsius' soul into a Robo-Ky's body and then left her. In Zappa's story mode, after Zappa returned a destroyed Robo-Ky in a friendly manner, he tries to experiment him after thanking him.
 * I-No: Crosses it brutally in the alternate future by befriending a teenage Ky, driving him into saving her in a hopeless situation and watching him suffer a nasty death and laughing at it, resulting in a dystopian future where Dizzy has turned bad and tries to annihilate mankind and no one can do anything about it.
 * M. Bison: Where do we even begin?!
 * Killed his own father when he was young.
 * Had Juri Han's parents murdered by a Shadaloo death squad.
 * Brainwashed Ken Masters and made him fight his best friend Ryu to the death.
 * Tried to kill Sakura in front of Ryu after she saved his life by taking a Psycho Crusher that was meant for him.
 * Tried to cause a nuclear holocaust by detonating every nuclear warhead on Earth with a doomsday code stolen from MI6.
 * Murdered Guile's friend, Charlie Nash.
 * Murdered Chun-Li's father.
 * Has attempted to take over the world numerous times.
 * Mother Mayhem: Was originally just an extremist who for all her spying on the thoughts of civilians and mentally torturing and destroying those that "disturbed the peace" believed she was serving a higher purpose by keeping Praetoria running perfectly. But when Mother Mayhem was given a drink of the Well of the Furies from Emperor Cole to increase her powers to that of a god she quickly became addicted to power and domination. Once the true colors of the Praetors are exposed to the citizens on live T.V. Mother finally decides that the only way to keep her "children of Praetoria" from turning on her and the other Praetors is to rob the entire populace of their free-will and psychically possess every single citizen as a hive-mind governed by her will.
 * Sofia Lamb: Suffocated her own daughter, Eleanor, to prevent Subject Delta reaching her. This stopped Eleanor's heart and broke the bond that the two shared, and (due to his mental conditioning) Delta started to slowly die as the game progressed.
 * Yevgeny Borisovitch Volgin: Fired an American-made Davy Crockett at Sokolov's research facility, destroying it and framing the U.S Goverment for this. He also did this as an intention of making the intelligence agencies believe that The Boss was the one who launched the nuke. This sparked an internation incident and began Operation Snake Eater.
 * Revolver Ocelot/Liquid Ocelot: Commands his troopers to slaughter an entire barrack of United States Marines when they're defenseless and crippled from the SOP system. To add insult to injury, he also tells Vamp to burn "Big Boss's" corpse (unbeknownst to everyone, it was really Solidus Snake's brain dead body) in front of the latter's lover, EVA, which ultimately led to her death when she tried to salvage it.
 * Magolor: He lied to Kirby to get him to help repair the Lor Starcutter. He then had Kirby defeat Landia so he could steal the Master Crown. Upon obtaining the Master Crown, Magolor instantly went insane from the limitless power and went to take over the ENTIRE UNIVERSE. He even threatened to destroy Kirby's planet first "for being such a big help." He even went as far as to kill Kirby himself after his Doomers failed to stop him.
 * Tohru Adachi: He either crossed it when tried to rape Mayumi Yamano, but ended killed her in accident and did the same with Saki Konishi, or when he manipulated Taro Namatame into "doing the rest" of his dirty work, but he officially crossed it when he revealed that he initially did it for fun. Worse, during the confrontation, Adachi confessed that aside for fun, he states human life and his own was complete nihilistic. So he decides to usher a new era where everyone live as Shadows, thinking that he making a better world by doing so.
 * Alex Mercer: In Prototype 2, he crossed it by intentionally starting a second outbreak in New York, resulting in the deaths of countless innocents. He also plans to spread it beyond NY and eventually infect the entire world with Amaya Heller as the catalyst due to her unique DNA that potentially enable her to control Blacklight Virus like James Heller. His MEH crossing deed made her sister, Dana Mercer realized that her brother has died, something that should had been realized by her long ago (Alex Mercer was in fact, already dead at beginning in Prototype, while his body possessed by the virus that he released).
 * Malthael: Crosses it by using his Reaper army to slaughter whole inhabitants of Pandemonium Fortress no matter who they are (angels or humans whom chosen to be it's guardian) and use the place to use Black Soulstone's power to reap demonic part of human souls. This act made everyone shocked, includes Imperius whom helpless and left no choice to help Nephalem hero to stop him.
 * Saix from Kingdom Hearts tricks Roxas and Xion, 2 best friends into fighting each other to see who is worthy to remain in Organization XIII.
 * Scolar Visari: Ruled planet Helghan with an iron fist and used the Helghast Military to kill and/or arrest all who opposed his rule as Autarch. Founded the Helghan Empire as a fascist state and blamed humans for the Helghast people's suffering and invaded Vekta. Stole a nuclear bomb called the Red Dust and used it on Pyrrhus City (Helghan Capitol) killing both helghast and human soldiers alike.
 * Jorhan Stahl: Worked with Visari with the plot to nuke Pyrrhus. Experimented on many POWs with the terricide and used his company's influence to attempt to seize power and rule the Helghast state. Killed Admiral Orlock and plotted to destroy the entire human population of earth with his weapons and control the surviving humans under his own regime. Destroyed the invasion fleet leaving Helghan defenseless and did it to make the senate beg to him for mercy and become Autarch. Years later he arms and finances the Black Hand led by Vladko Tyran to help bring down New Helghan and take over the rest of Vekta. *Conker the Squirrel: He may have crossed it after he had to make a sacrifice to a dinosaur god, Uga Diety, by smashing a baby dinosaur that was just hatched, so the god's statue would open and Conker could pass.
 * Adria (Diablo): Betrayed Tyrael and protagonists by reveal her true allegiance with Diablo by sacrifice Leah as Diablo's vessel in order to resurrect Diablo as singular Prime Evil and let him attack the Heaven. Other few reason to hate her was:
 * First, her manipulative nature. When her dark past where she was once befriend with Maghda revealed, heroes asks her about this, in which she claimed that she has betray her. This was proved by Maghda's minions torture her when heroes save her. Moments when she rescued, however, was her own ruse to manipulate protagonists all along, which she has already did from long ago: Start off from manipulate Deckard Cain so Leah can stay with him, found and used incomplete Black Soulstone to find essence of fallen Evils (Baal, Mephisto, Andariel, Duriel, and namely Diablo himself), had herself tortured by Maghda’s minions so heroes rescues her, and finally, acquire rest of Evil’s essences(Belial and Azmodan).
 * When the heroes reunite with her both, to avenge Leah’s death and ask Malthael’s whereabouts, they caught her turn herself into succubus like abomination, effectively prove that all this time, she is an irredeemable demon whom humanity has been since the moment she join forces with Diablo who possessed the wanderer.
 * Sachiko Shinozaki: Causes death of many people who trapped within the pocket dimension called Heavenly Host Elementary School even before protagonists themselves trapped inside. In OVA Tortured Souls, though she eventually find the peace and managed to go to the afterlife, her damage was too greated for survived protagonists: Satoshi lost his charm during her terror, and made him used other charms that belongs to one of his friends, causes the only thing that returned to real world were his severed arms, heavily traumatized other survived protagonists, namely Ayumi and Naomi.
 * Aran Ryan: Cheats in boxing by using elbow slams and headbutts, threatens any spectators, and brings a concealed weapon, which is completely illegal in boxing, into a fight against Little Mac.
 * Lord Brevon: If beheading the King of Shuigang in front of his son, Prince Dail, and then corrupting him into his loyal servant at the beginning of the game Freedom Planet wasn't heinous enough to throw him over the edge of the MEH, it's torturing Lilac in front of Torque to get information out of her and later transforming the sweet and innocent Milla into a mindless monster mutant and forcing Lilac and Carol to fight her until she is comatose that definitely does it.
 * Jane (The Walking Dead): She crosses it when she tricks Kenny into thinking that AJ had died, causing him to attack her, which leads to his death if the player chooses to shoot him. Depending on the player's choice, Clementine is angered by Jane's actions and leaves her behind.
 * Master Xehanort: Crosses this when he kills Master Eraques and destroys the Land of Departure, the home of Keyblade wielders, all so he can awaken Terra's inner darkness and possess him.
 * Copy X: In Mega Man Zero 3, he and Dr. Weil crossed a MEH when they sent a missile to a residential area with the purpose of catching the Dark Elf and empower Omega. Said missile took millions of human lifes. Copy X's actions were morally ambiguous up until that point. He crossed it when he sent lots of innocent Reploids to their deaths by unfair judgements for the sake of controlling the energy crisis, but in that act, he did not regard the human lives that would be lost with the missile.

Spider-Man

 * Doctor Octopus: He exchanged his mind with Spider-Man and left him in his body to die. He's not only the actual killer of Spider-man, but also he stole his position.
 * Green Goblin: Norman Osborn, as the first Green Goblin, famously crossed the line when he kills Gwen Stacy. In Sam Raimi's film series, on the other hand, his film counterpart kills a lot of people by his lethal weapons and vows to kill Mary Jane Watson in a painful way in front of Spider-Man because he failed to do something similar with what his comic book counterpart did to Gwen (though in this case his victims were Mary Jane and a tramway full of children). However, his The Amazing Spider-Man film counterpart (though the mantle was at the hands of Harry Osborn), succeeds in doing so, nearly causing Spider-Man to quit his days as a hero.

Date A Live Manga

 * Minerva Liddell: Like Isaac Westcott, Minerva has numerous acts that crosses the line and making her one of the most despicable villains in Date A Live franchise:
 * She first crossed after dressing Ashcroft Unit and have mentally raped Artemisia.
 * Crossed again when she was about to kill Cecil O'Brien in front of Artemisia and made her enter in full despair.
 * Crossed soon brutally after tortured the 3 Artemisia's best friends only to give a lesson in Artemisia.
 * Crossed after tried to rape Okamine Mike, a 10 years old girl who is a Wizard from AST in Tengu City, and tried to kill her to rape her body after death.
 * Crossed in her last moments of her life, when she ignored every chance of redemption and refused to give up, and in a last attack, she tried to decapitate Artemisia, she was just prevented after she was killed by Mikie Okamine and Origami Tobiichi.
 * Edgar F. Caroll: Crossed when he used the memories stolen from Artemisia B. Ashcroft to create a new Combat Realizer Units to take over the Deus.Ex.Machina Industries without care about the atrocity that he was doing. His crime resulted in the creation of Ashcroft Assembly and the horrible tortures caused by Minerva Liddell in Artemisia's best friends of Artemisia.

X-Men

 * Sabretooth: Crosses it when he killed Copycat just to get Deadpool to rejoin Weapon X, this is one of the few deaths in comic books where the character stays dead.
 * Magneto crosses it when he ripped the adamantium right off of Wolverine's skeleton, nearly killing him.
 * Apocalypse: Since he tried to commit genocide of the weaker, but turning Wolverine into one of his riders is noteworthy.
 * Mister Sinister: Sinister cloned Jean Grey in the form of Madelyn Pryor so that Cyclops would have a child with her, which Sinister would view as the ultimate mutant. He was also involved in Stryfe's attempted assassination of Xavier and trading Cyclops and Jean Grey to Stryfe in exchange for their DNA. However, Stryfe actually gave Sinister the Legacy Virus, which would terrorize mutant (and eventually human) life and lead to the deaths of several mutants.

MLP

 * Queen Chrysalis - In the comics, she violently kills a cat in front of the Cutie Mark Crusaders, and it is implied that this was not the only cat she killed, and none of them are seen after her defeat in Issue 4. She also tries to force Twilight to become her apprentice by threatening her friends and plans to drain Twilight of her love and make her kill her friends herself.
 * Pinkamena: Crosses it when she kills Rainbow Dash.
 * Pinkie Pie (Smile HD): She clearly crosses it when she kills her friends just because they laughed at her for a long time.

Batman

 * Joker: Crossed it when he kidnaps Jason Todd and beats him to near death with a crowbar and then blew up the house he was in, killing him. The Joker in Under the Red Hood did the same thing in the beginning of the film. He also shot Barbara Gordon and crippled her and killed around 2,000 people.
 * Bane: Crossed it when he broke Batman's back.
 * Two-Face: He willingly became the same criminal as he used to be prior surgical reconstruction of his face.
 * Scarecrow: Killed scientists at the Gotham University.
 * Victor Zsasz: He killed as many people as the marks on his body he carved.
 * Clayface: He killed several of his movie crew.
 * Hush: he tried to kill his parents to inherit their fortune.

Order of the Stick

 * Xykon: He murdered his parents and his grandmother, allowed Right-Eye's family to be murdered when he had the opportunity to prevent it from happening, murdered the Sapphire Guard by driving them all to insanity (thus causing them to turn on each other), and trapped Lirian and Dorukan's souls inside a gem, such cementing him as the most depraved villain in the Order of the Stick.
 * Redcloak: Though not as evil as his boss Xykon, he also crossed the line when he murdered his brother Right-Eye so that he could continue his plans to make a better world for the goblins, even after he had told him that the plan wasn't worth the casualties that it would cause.
 * Nale: Stabs his brother Elan in the back after he politely declines to join the Linear Guild, and murders the citizens of Cliffport simply to lure the authorities to his hideout so that he could impersonate Elan and infiltrate the Order of the Stick.
 * Tarquin: Though initially appearing to be a loving father, he burns several slaves that had escaped from him alive, believing that this would be a good present for his son. He also forced Enor and Gannji to fight each other to the death.
 * Malack: Planned to continue Tarquin's empire after he was gone, murdering a thousand people every single day to sacrifice them to his god Nergal. Also, he murdered his former friend Durkon and transformed him into a vampire, though he planned to relinquish his control over him after he and the Linear Guild had secured Girard's Gate.

Slenderverse

 * Slender Man: Many people in The Slender Man Mythos believed he crossed this when he turned children into proxies.
 * HABIT: Crossed the Moral Event Horizon when he kills Evan's girlfriend and ate his baby.
 * The Rake: After he kills Sparky, Alex's dog, Jessie, Evan's former girlfriend, and presumably kills Alex, Jeff's younger brother.
 * Victor (MyDarkJournal): Crosses the Moral Event Horizon when he kidnaps the main protagonist of Clover in Chicago, and emotionally (and possibly physically) tortures her.
 * Ellie: Murders the Anti-Body]] and Bowie.
 * 1AmTheHelp3r: After he burns Natalie's childhood home down.
 * Novus Ordo Europa (also known as The Order): After they brutally mutilate Chris and Alex's families.
 * The Observer: Crosses the horizon when he murders Noah's friend, Sarah.

The Walking Dead

 * Shane: He attempts to kill Rick.
 * The Governor: He chops off Rick's hand and rapes Michonne.
 * Negan: He bashes Glenn's head with Lucille, killing him.
 * Alpha: She decapitates 12 people, including a child and a pregnant woman, and uses their reanimated heads for her border.

Others

 * Nostalgia Critic: In the Conquest of the Commercials, he use to edit the commercial that he kill the Pokémon characters in the bus by crushing, and making fun at the Pokémon fans very sadistic which he don't like the first film.
 * Uncle Johnny: Became one of the most hated villain in the Creepypasta mythos by raping and murdering his niece Sally Williams.
 * Aurelian Titus: He kidnapped King Maric and kept him captive for years to take his magical blood and use it to become a powerful mage.
 * Big Daddy: Crosses it when it was revealed that he kidnapped Hit Girl and trained her to be an assassin and his whole origin story was a lie.
 * Broccoli Overlord: Uses a laser to turn veggies into zombies. This caused havoc throughout the episode although the only fruit that was killed was the pineapple (and possibly, the banana) however his plan was foiled by Orange's annoying laugh blowing the veggie zombies up.
 * Jeff the Killer: Killed his entire family for fun.
 * Randy, Keith & Troy: Attempted to kill Jeff at a child's birthday party, pointing guns at kids and their families, threatening to shoot and kill anyone who tries to interfere.
 * Red (Creepypasta): Kill at Zachary's girlfriend Melissa at the Traffic Attack, and Killing at Godzilla, Mothra, Anguirus and Solomon.
 * Darth Krayt: Kills emperor and proclaims himself as new emperor of the galaxy, he creates new sith order, conquers the galaxy and kills most of population of planet Mon Calamari.
 * Ultron: During the story arc "The Age of Ultron", he crosses it when he cloned countless times and killed almost every hero in the Marvel Universe.
 * Sonic.EXE: For killing his friends Tails, Knuckles, Amy Rose, Cream and Sally (and even Dr. Robotnik), he began to turn them into the demon darkness, killing Tom and Tom's friend Kyle, and torture at the player who play Sonic.EXE and Sally.EXE games.
 * Lumpy: In the episode We're Scrooged, he deliberately lets Toothy fall into a box of wind-up teeth toys and get ripped apart, then sells his body parts for his own greedy expense.
 * Shifty: In Sea What I Found, he and Lifty are trapped in a gold submarine which melts from an underwater volcano. Even though having the chance to rescue his brother, Shifty instead takes the jewels off his arms.
 * Flippy (evil side): In Hide & Seek, he murders every other character in the episode, though he is mostly said to have crossed the line because many fans assumed that his flip-outs would be a running gag throughout the series.
 * Drip Tiberius Rat: While having crossed it in life, his particular Moral Event Horizon-crossing action in the comic's events is molesting his son Fnar, who can only be harmed by his parents while in Hell, just to get revenge on Jack for foiling an attempted rape.
 * Harriet Hill: Tries to convince the Catholic Church into burning Larisa at the stake, and later threatens to severely beat her son, Landon, if she ever saw him with Larisa again.
 * Terra of the Left: Had commited countless attrocities against both Non-Christians and Non-Catholics alike, experimented on Non-Catholic tourists in Rome to create his Execution of Light spell, used the citizens of Avignon, France to distract the Academy City Forces from stopping him and believed in commitng acts of murder against Non-Catholics was a way from him and the other members of the Roman Orthodox Church to achieve Ultimate Salvation and believed that he would acquire such an achievement only to be remined by Acqua of the Back.

Live-action TV

 * Queen Bansheera: Showed no regard for her own minions and even forced Diabolico to destroy the Power Rangers with Loki in between them.
 * Kingpin (Marvel Cinematic Universe): despite being a tragic villain (being abused by his psychotic father) he crosses it twice when he kills Elena Cardenas and Ben Urich.
 * Niklaus Mikaelson: has usually done This in The Vampire Diaries by killing Tyler Lockwood's mother due to his hybrid army's betrayal, turned Aunt Jenna into a vampire, killed Elena, corrupted Stefan and has threatened to kill Jeremy should Bonnie undo the linking spell. He also does this when daggering his siblings and in The Originals, he gave Elijah and Joshua werewolf bites, he stabbed Elijah, hasn't even apologized to Davina and Joshua for what he had done to them, he has killed his mother he was even about to kill his own sister, Rebekah and he even killed his own father (this is debately an anti-heroic deed as he did so that Esther wouldn't come after his daughter).
 * Esther Mikaelson: She has ordered the assassination of Klaus and Hayley's child, she has always wanted her dead, she kidnapped Elijah and psychologically abused his mind just so that he could accept her offer, she wanted to have all of her children killed and went so far as to making a deal with Mikael and Finn to have Klaus and his allies dead. She has also favored Finn over her other children.
 * Mikael: He does this by psychologically torturing Klaus when he was a child (due to being the product of infidelity) and has constantly tried to kill him, he has favored Elijah and Rebekah and has even gone so far as to wanting to kill his own children.
 * The Reaper (Criminal Minds): Cross it when his resourceless murder of agent Hotcher's wife and teases him about it causing hotcher to beat him to death
 * Creepy Connie Thompson: When Jessie Prescott wrote a play with Luke staring, she auditions as Luke's love interest, attacking and injuring her competition for the role. When Luke refuses to kiss her, she tries to kill him with a flamethrower.
 * Dandy Mott: Debatable when he crosses the horizon, but its likely at the finale, when he massacres all the remaining freaks except for the three protagonists.
 * Nora Dershlit: In iCarly, she abducts the iCarly crew with no intention of letting them go, and attempts to kill Gibby, in her second appearance she and her family kidnap them and even tortures Spencer to keep them from escaping, and tries to kill Mrs. Benson and T-Bone for trying to save them. In "Sam and Cat", she abducts Dice simply to hurt Sam.
 * Terry Milkovich: Either crosses it when he beats his son Mickey and his lover Ian Galagher when he catches them in bed and forces Mickey to have sex with a prostitute and have Ian watch. After the resulting grandchild is baptised, and Mickey announces he is gay, Terry tries to beat him to death.
 * Arnie Grunwald: Tortured the residents at a shelter for the blind like dirt.
 * Meg (The Haunting Hour): willingly left Lisa and Amelia to die.
 * Megan Parker: Allowing Drake and Josh to be trapped in the treehouse and not allowed them any means of escape. Plus, she also plucked Josh at one point and said she did it "Because I knew it would hurt you.".
 * Ava Jerome: Killed Connie and framed A.J., resulting in his death at Sonny's hands. When A.J. was in his hospital bed before his death from his wounds, she tried to kill him by blocking his breathing tube. Plus, manipulated Sonny with A.J.'s death until the point when Sonny discovered the truth.
 * Fluke Spencer: Using emotional blackmail to convince Tracy not to get a prenup on him (so he can funnel his drug money into ELQ), threatening Ned with a gun after he ruins his plan, hitting on Kiki, ordering Lucas' shooting, killing his own man who did it to cover his tracks, threatening Emma to Spencer after Spencer discovers incriminating information about him (showing that he would harm a child), threatening Julian's family and forcing him to stay in the mob, forcing Julian to help him incriminate Ric as a scapegoat, nearly killing Lucas by blocking his breathing tube in his hospital bed, calling Lulu a "b---ch", speaking dirty about Tracy, plotting to take down Sonny, plotting with Tracy to steal ELQ away from Michael and being the true head of the Jerome Crime Family. Above all, it's when he's revealed to indeed be an impostor (having watched the real Luke for years) and holding Luke hostage. This strips him of all redeeming qualities as we still don't know who he really is, but know it's not Luke being brainwashed into doing what we thought he was doing (and we're convinced by this revelation that the real Luke would never willingly commit such acts of evil).
 * Lizzie Samuels: Delusional, Lizzie murders her younger sister Mika and attempts to murder baby Judith in an attempt to show Carol and Tyreese that walkers aren't different.
 * The Governor: Crossed it when he deceived a National Guard unit and massacred them all for their supplies. He later decapitated Hershel Greene without remorse.
 * Walter White: Attempted poisoning of an 8 year-old boy to convince Jesse Pinkman that it was his former employer Gustavo Fring so that he could have Jesse's assistance in order to assassinate him successfully. Killing Mike and/or his ten guys, threatening to set Hank up as his scapegoat or hiring Jack and his men to try to kill Jesse/handing him over to them could also qualify.
 * Gustavo Fring: Threatening to have Walt's family killed if he interferes in his plan to have Hank killed for getting too close. Had he been the one who had Brock poisoned, that would have been it.
 * Arrowverse:
 * Slade Wilson/Deathstroke: Crosses the line in The Man Under the Hood when it was revealed that he was using Roy's blood to create his army. If Oliver didn't save him, Roy would have died. He later murdered Moira Queen in front of both of her children.
 * Malcolm Merlyn/Dark Archer: In the finale of the first season of Arrow, he uses an earthquake device to destroy the Glades, killing hundreds of innocence including his own son Tommy.
 * Amanda Waller: Although she believed herself to be acting in the good of the whole country, threatening to destroy a city filled with millions of innocent people just to stop Slade Wilson showcased her immorality.
 * Damien Darhk: Crossed the line when he murdered Laurel Lance using Oliver’s arrow to torment him. A case can also be made that he crossed it by kidnapping Oliver’s son William to blackmail Oliver into dropping out of the Mayoral race.
 * Andrew Diggle: Despite having multiple opportunities to side with Team Arrow, he chooses to stay aligned to HIVE, making it clear through conversations with his brother John that he would never be redeemed through comments about torturing John’s daughter. John later realized this and was forced to shoot him dead.
 * Lonnie Machin: Just to kill Damien Darhk, he was willing to destroy Tevat Noah, potentially dooming the entire planet. When confronted with that knowledge, he completely brushed it off by saying “Did I leave you with the impression that I was a rational guy?”
 * Adrian Chase/Prometheus: As a last ditch effort to try to redeem him, Green Arrow tells Adrian’s wife Doris about his murders as Prometheus. Adrian promptly murders his own wife to prevent that knowledge from going public.
 * Ricardo Diaz/Dragon: Diaz is revealed to have manipulated Cayden James into wanting to destroy Star City before murdering James to begin an ascension to take control of Star City. It is also revealed that he is the one that created the doctored image of Oliver in the Green Arrow suit to begin an investigation that later leads to an impeachment. He also sets his childhood bully on fire out of revenge, an act that revolted Black Siren, a ruthless killer in her own right.
 * Eobard Thawne/Reverse-Flash: Not only does he kill Cisco in an erased timeline, it is later revealed that he is the one who killed Barry’s mother. He later is willing to ally himself with the Nazis of Earth-X to take over Earth-1 and kill Barry once and for all.
 * Hunter Zolomon/Zoom: To prove that Barry and him are the same, he murders Barry’s father Henry at his childhood home, the same place that Barry witnessed his mother die.
 * Savitar: Despite Barry and Team Flash’s attempts to remind him of happier times, Savitar instead chooses to reject redemption and opts to destroy S.T.A.R Labs instead. This is if you don’t count him murdering H.R. Wells in an attempt to kill Iris West and ensure his existance as his crossing.
 * Clifford DeVoe/The Thinker: Simply because he was in the way, DeVoe chose to murder the corrupt warden of Iron Heights, Gregory Wolfe. He also used his mind control powers to force a security guard to kill himself, an act so disgusting it makes his wife and partner-in-crime Marlize ally with Team Flash to stop him.
 * Non & Indigo: When they could no longer use Myriad to control all humans on Earth-38, they resolved to use it to exterminate the humans instead.
 * Rhea: After Lar Gand, her husband, allowed their son Mon-El to return to Earth, as he had found a happiness that he never had on their home planet of Daxam, Rhea stabbed Lar Gand and resolved to take over Earth to turn it into a new Daxam.
 * Reign: In her first appearance, she publicly beat Supergirl into a coma.
 * Vandal Savage: An immortal whose entire existence revolves around killing all the reincarnations of Khufu and Chay-Ara, he is willing to annihilate entire cities just to kill the two. In an erased timeline, he completely destroyed Central City, and he later took over the entire world to rule it with an iron fist after exterminating much of the human population, including Rip Hunter’s wife and son.
 * Time Masters: Although they were originally believed to be a heroic organization, Druce later confesses that they had Vandal Savage kill Rip’s wife and son and had been manipulating the Legends to force them to make bad decisions.
 * Mallus: As a demon of the highest order, Mallus was evil long before the Legends encountered him. Within the show, however, his crossing could be considered corrupting Nora Darhk into his host.
 * Manny: It is revealed that Manny is behind the Rising Darkness Constantine had been battling.
 * Earth-X Nazis: Although they were evil before traveling to Earth-1, their immorality can be showcased through Earth-X’s Tommy Merlyn pretending to be a reluctant villain before making it clear that none of the Nazi forces could be redeemed. Harry Wells even comments that no sane person ever travels to Earth-X due to the strength of the evil there.
 * James Moriarty: Crosses the line during the events of "The Reichenbach Fall", when he orchestrates an elaborate plan to destroy every aspect of Sherlock's life and public image; this includes managing to convince the police that Sherlock was a fraud, and that Moriarty was invented by Sherlock and was really an actor named Richard Brook, which was essentially saying that Sherlock was committing the crimes himself and staging them just to satisfy his obsession for solving his crimes. Moriarty even drives Sherlock to the point of committing suicide (where the only alternative was that John, DI Lestrade, and Mrs. Hudson would be killed by Moriarty's associates) by jumping from the rooftop of a building. However, it is later revealed that Sherlock faked his death in order to covertly take down the rest of Moriarty's criminal empire in secret.
 * Sylar: He crosses the line when he slit Nathan Petrelli's throat.
 * Gorog: Ordering the death of Justin Russo despite the fact he was responsible for his success, simply because he did not need him.
 * Vancome Lady: She crossed it when she told a little girl that she (the little girl) was the reason her father drinks, making the child hate herself.
 * Todd Alquist: Crosses it when he killed Drew Sharp who was just a young boy, then later he kills Jesse Pinkman's ex-girlfriend, Andrea Cantillo.
 * Jack Welker: Killing Hank despite Walt's pleas and attempts to pay him off not to. Plus, threatening Brock's life to Jesse after Todd kills Andrea.
 * Laurie Forman: Caused Michael and Jackie's third breakup by tricking Michael into kissing her while Jackie watched.
 * Vice Principal Stern: Cursed Ethan to see a constant vision of his worst fear, simply as warning not to cross him.
 * Peter Hale: Killing his niece for her alpha powers.
 * Kate Argent: Seducing an underaged Derek Hale to get information on his werewolf family and burns their house down, killing most of them including Derek's human relatives.
 * Rassilon: Tried to initiate the Ultimate Sanction, which would wipe out all of time and space, just to insure the survival of the Time Lords.
 * Jake Skinner: Leaving Will to die and stealing his life.
 * Lilly D: Framing the real Lilly Carbo for various crimes and turning her own mother against her.
 * Gerard Argent: Killing an innocent omega werewolf and declaring that all werewolves in beacon hills regardless of their innocence. This was the first of many attrocities in his plan to become a werewolf to cure his cancer, making him a hypocrite.
 * Kali (Teen Wolf): Kills Erica and later makes Derek kill another one of his betas, Boyd.
 * Matt Daehler: Though murdering everyone who let him drown when he was a child seems to make him a tragic villain, he arguably crosses the line when he murders one of his victims himself via suffocating her, after the Kanima refused to do so, right after she had just given birth, leaving her child an orphan. Once he holds Scott, Stiles and his father hostage at the Sheriff Station, he has the Kanima murder several innocent cops. This all in turn causes him to start turning into a Kanima himself for breaking the rules.
 * Nevel Papperman: Framing Carly Shay in intentionally pushing Shelby Marx's grandmother down, hoping to get Carly beaten up.
 * Zoe Rivas: Crosses it in season 14 of Degrassi. Examples are forcing Power Cheer to Oomfchat nudes for money, taking a topless picture of Frankie and using it to blackmail her, and even making Frankie her scapegoat. She showed no remorse for any of these things, as according to her, she was tired of being treated like a victim. In season 13, she slut-shamed Maya Matlin as payback for stealing her boyfriend.
 * Max Hudson: Has his wife killed and later makes fun of her death on his radio show. During his and Monk's second confrontation in his studio, he pokes fun at his late wife's, Trudy's, death on live radio, enraging Monk so much that he physically attacks him. Even his radio sidekicks are appalled by his behavior.
 * Jesse (My Babysitter's a Vampire): Biting Ethan and forcing Sarah to drink his venom, forcing her to give up her humanity.
 * Jett Stetson: Tried to strong arm Kendall Knight and Jo Taylor into breaking up by having Jo's publicist advertise a relationship between Jo and Jett. When confronted, they threaten to ruin Jo's job on her TV show if she doesn't play along as Jett has more fans then her.
 * Dukat: His cold-blooded murder of Jadzia Dax (who was simply in his way) signaled a major turning point in his voyage from a trouble anti-hero to an outright monster.
 * Morgan Clark: During the Earth Alliance Civil War, President Clark ordered the deaths of civilians who were injured on the battle field. An order which lead to his downfall because John Sheridan ordered the Rangers to go on the offensive against Clark's Regime.
 * Angelus: Shortly after he was sired by Darla, his first victims where his family. They were the first in what would be several dozen victims Angelus killed/tortured for over a century before he was cursed by gypsies with a soul.
 * Warren Mears: Either crossed it with the attempted rape and murder of his ex-girlfriend Katrina or when he killed Tara McClay. The latter is considered one of the most infamous crossings in television history.
 * Herr Otto Flick: From the start he was always implied to be dangerous, as senior member of the Gestapo, although appearing as mostly a comedy villain, he demonstrated just how dangerous he was in late season two, when he captured and tortured Captain Von Storm, Captain Geering and Rene. In which he almost crushed them to death (something they only survived because General Von Klinkerhoffen saved them), even proceeding after they told him everything they knew. The moment is made more clear by the fact he broke his normal emotionless personality to demonstrate obvious pleasure in there suffering.
 * Tuatha: Crossed the MEH by killing countless innocent people, shrinking two treasure hunting hikers who accidentally set her free and feeding them to her snake. She also murders an old woman named Betty and casts a spell to make the sisters powerless to stop her, leaving Kyle as the only one who can vanquish her.
 * Lex Luthor from Smallville: He is already beyond the Moral Event Horizon.
 * In "Subterranean", he imprisoned several meteor freaks to make experiments in 33.1.
 * In the Season Six, it's revealed that he drugged Lana Lang with a chemical who made her believe that she was waiting for a son of him.
 * In "Persona", he ordered to kill a clone of his late brother, Julian.
 * In "Descent", he pushed Lionel Luthor out of a window to his death after Lionel refuses to divulge the identity of the legendary Traveler (Clark Kent).
 * In "Requiem", he forced Clark and Lana to separate, putting them to choose whether Lana absorbed the Kryptonite bomb and became unable to be near Clark anymore or let the bomb destroy half Metropolis.
 * Davis Bloome/Doomsday: Murders Jimmy Olsen after overhearing a conversation between Jimmy and Chloe Sullivan in which Chloe reveals she only agreed to go into hiding with Davis only to protect Clark and not because she loved Davis; this occurred after Davis was separated from his Kryptonian alter-ego Doomsday.
 * Dian Lamitan: Has crosses the Moral Event Horizon several times which includes of framing her husband Bugna as a traitor to Rajah Mangubat, forced her own daughter Marikit to abort her child from Bagani after discovering the issue of his fraud as well as drugging her, turned her stepdaughter Amaya into a slave, abuses Dal'lang, forcing her own daughters to marry a person they don't love, ordered to have her rival Hara Lingayan killed, betrays Angaway & some of her allies, told lies about Amaya several times and considered her an outcast & bribed many soldiers to do her bidding.
 * Helen Collins: After she killed her abusive father, she murders her sister after her sister tried to save her. She then took her name, Amanda, for her own before burning her home with her father's body and her sister inside.
 * Christy Jenkins: After the Charmed ones and her sister, Billie Jenkins, killed her demon master, Dumain, she attempts to kill her sister by hurling a fireball at her, but her sister deflects it back to her, killing her sister, an act that not only made Christy cross the MEH, but also redeemed Billie, albeit, Billie's redemption came at a terrible price; The Loss of her sister, the last remaining close relative she had after her parents were killed by the Triad.
 * Gideon: After he killed his friend, Sigmund, when he decided to tell the Charmed Ones of his betrayal and his plot to kill Piper's infant son.
 * Kira Nerys (Mirror Universe): After she killed Jennifer Sisko when protected Jake Sisko, her prime universe's counterpart's son, when she was escaping a Terran Rebellion-controlled Terok Nor.
 * Garret Jacob Hobbs: Crosses it when killing his wife when he was insane.
 * The Kidnapper (Hannibal): In the 4th episode of Hannibal, which is her only appearance, she left the children she kidnapped to kill their own families. *Clark Ingram: Framing Peter Bernardone for the murder of 15 women.
 * Abel Gideon: after he killed his wife and children.
 * Mr. Morden: after he ordered the death of Adira Tyree, via poisoning and blamed Lord Refa on it, just so he can motivate Adira's boyfriend and lover, Londo Mollari, into being an agent of Chaos for the Shadows. However, after Londo found out about this, he had Morden decapitated and his head placed on a pike where it remained until it was fully decomposed.
 * Trinity Killer: Crosses it when he kills Dexter's wife.
 * Daleks: Have committed countless war crimes and acts of pure evil and genocide across the universe over their species' history.
 * The Daleks arguably fully cross the MEH onscreen in "Evolution of the Daleks", when the rest of the Cult of Skaro betray Dalek Sec and resume the Daleks' evil and genocidal ways, rather than follow Sec in sacrificing their purity and emotionlessness for the sake of their future. This can be considered the Daleks' truest MEH-crossing, because they'd had an actual chance to be saved from the darkness and redeemed by sacrificing their evil old ways, but had instead refused to let go of their omnicidal xenophobia and concept of Dalek purity, thus forsaking the Daleks' only chance at a better existence.
 * Destiny (Mongrels): Though Destiny has committed many selfish, greedy, immoral, petty and cruel acts without any respect or regard for anyone other than herself over the course of the show, she crosses the Moral Event Horizon when she attempts to murder Gary, her own owner, with poison, all just so Marion wouldn't be favored by Gary when Marion temporarily became a second pet.
 * Dana Walsh/Jenny Scott: On 24. When lying and hiding her identity and old life from CTU and Cole (as well as assisting reluctantly in crimes that her ex-boyfriend and his partner commit), she still manages to maintain sympathy. Even when she kills Bill Prady and covers up his death, it's seen as an act of desperation by someone who'd felt they'd lost all other options. It's not until she calls Samir Mehran and she's revealed to have been a mole working for the terrorist the whole entire time that she is then established as a full blown enemy no longer worth rooting for. Somewhat subverted by her later torture and alliance with Jack and Cole, her still apparent feelings for Cole and her somewhat uncalled for execution at Jack's hands.
 * Patrick Kemp: Crosses the Moral Event Horizon either when he begins murdering werewolves using the decompression chamber, or when he murders Hennessey and exorcises Annie.
 * Dian Lamitan: She physically abuses Dal'lang, tries to kill Amaya when she was a kid, lied to Rajah Mangubat that Datu Bugna is a traitor as a revenge for slapping her for attacking Amaya and so she could easily stripped Amaya out of her position as a princess and turn her into a slave as well as abusing her, forced her favorite daughter Bai Marikit to divorced Bagani and marry his father instead by using a love potion on him then aborts her offspring with Bagani that made her insane and then drugged her so the rajah will never find out about this, conspired with Uray Hilway and Angaway after Rajah Mangubat betrayed her upon finding out her schemes and upon regaining her position as a Dian, she told lies about Amaya about her being an evil person & declared her as an outcast, blackmails her less favorite daughter Binayaan by harming Dal'lang who had become her adoptive mother, she conspired against Angaway on her own as well (upon finding out Amaya and Bagani are planning to attack him) by bribing Datu Pulajan into joining her side and then invited them into a ball by serving poison on both sides excluding hers', had her rival Hara Lingayan killed secretly, bribed many soldiers and officials to do her bidding, took Dayaw as a hostage so that Posaka will surrender Amaya to her but was secretly planning to kill both of them but Dayaw escapes upon finding out and commits suicide, which Lamitan quickly finishes him off, had Asinas killed for conspiring against her, betrayed Datu Pulajan after discovering he made a secret alliance with Amaya by poisoning him and taking control of his army and tried to massacre civilians in an attempt to force Amaya and Bagani's forces to surrender, only to fail. She even took Alunsina, who was a little girl, hostage and warns everyone she will kill her if they tried to stop her so she could escape her death penalty and escape to a faraway land. Most of her actions are avenged when Rajah Mangubat stripped her off her position as a Dian, when Amaya chopped her hand off and voodoo her to lose her agimat's power and when Amaya finally kills her by summoning Bakunawa to devour her.
 * Xena: in an alternate reality where Xena was never reformed, had Gabrielle, who was the one person Xena love the most in the Prime Xenaverse reality, crucified for standing upto Xena's reign of terror.
 * Veronica Harrington in "The Haves and the Have Nots" crosses the Moral Event Horizon a few times:
 * After her son Jeffrey comes out of the closet, she gives him a hateful speech about how his homosexuality is a punishment from God for her having an abortion in college, and essentially wishes her son was dead.
 * Firing Jeffrey from his job as a counselor at her rehab clinic, and depriving him of his finances and apartment.
 * Blackmailing Jeffrey into dating women by threatening to have him arrested for the murder of a young girl (Wyatt Cryer, while high on drugs, drove Jeffrey's Sedan and hit and killed the girl, and also left Benny Young in a coma).
 * Threatening to have Quincy Maxwell's family murdered if he doesn't back down.
 * Ordering Quincy, a convicted murderer, to beat up Jeffrey if he does not reveal Candace's whereabouts.
 * Arranging for Jeffrey to impregnate Melissa so he would be forced to marry her.
 * Attempting to kill her husband David by setting fire to their house. **Blackmailing Melissa's family by threatening to foreclose on their house so her cancer-afflicted father won't be able to get his medication. **Arranging for Wyatt to be raped in prison.
 * Ginis (Zyuohger): One of the sickest villains in live-action Japanese media, he endlessly commits atrocities at any chances possible:
 * After sending enough contestants to make the humans suffer, he coldly unleashed a shrinking barrier that disintigrates anything, while setting up a planet-destroying robot, G.I.F.T. in case the barrier is turned off.
 * Kidnaps and brainwashes the friendless Misao Mondou to become his own contestant, at the cost of three Zyumen's lives.
 * Hiring Bangray, a great animal hunter, to spice up his game. Said hunter bullies people's with idealisms and willing to send people into emotional trials.
 * Sparing Quval after an attempted takeover, in a vile act to see Quval destroying everything just to amuse himself.
 * Causes multi-planetary destruction just because he loathes from being made from inferior beings.
 * When Naria, his most loyal assistant, admits her loyalty regardless of who he is, which happens after she realizes his secret of being made from inferior beings, he kills her without a second thought.
 * Despising any form of pity and compassion and killing anyone showing it to him.
 * Throughout the series, he shows no care when his underlings die, as long as he gets some enjoyment.

Supernatural

 * Lucifer: Murders the women and children of a small town and sacrifices several of his loyal demons (who are possessing the town's men) as part of a ritual to free Death; about the demons after they're killed, he nonchalantly remarks that they are "just demons," showing he doesn't care about them despite the fact that they adore him and worship him as their god. Lucifer also, before the series, was responsible both for corrupting the original humans and for fathering the demon race by torturing and corrupting Lilith into the first demon (a deed which as revealed in Season 10, done immediately after infected by The Darkness' malice).
 * Gordon Walker: Arguably crossed the Moral Event Horizon at one of several points through the Supernatural series:
 * Before the events of the series, he hunted down and killed his own sister after discovering she'd been turned into a vampire.
 * Viciously tortured and attempted to wipe out and murder Lenore and her nest despite being aware that they were only killing cattle and were genuinely trying to avoid harming humans. In anime adaptation, he did it on a family of good vampires instead.
 * Started feeding on and turning humans after becoming a vampire, and attempted to kill Sam despite the latter's special child powers having become inactive since Azazel's death.

Sleepy Hollow

 * Moloch: He is a corruptive, emotionless and cruel demon king who enjoys punishment and torture towards his failed minion. He makes many acts that cross the MEH and making him so far the worst antagonist of the whole series:
 * Season 1:
 * "Pilot": He famously crosses it when snapping Andy Brooks’ neck for his failure and then changes the video footage and makes it to show as if Andy committed suicide, confusing Captain Frank Irving.
 * "Blood Moon": Moloch revives Andy to make him his soulless undead servant, and then Moloch forces Andy to release the burning soul Serilda of Abaddon, one of his witch servants and the leader of the Order of Blood Moon. Serilda’s quest for reconstructing her body causes a man (who is a descendent of an anti-witchcraft judge) burned alive in his car.
 * "Necromancer": In the past, Moloch let his Hessian minions shot Abraham van Brunt, the former best friend of Ichabod and the ex-fiancé of Katrina. Then, Moloch transformed Abraham into the Horseman of Death after promising him to give him Katrina as his price, which was one of the main reasons of Katrina’s imprisonment in Purgatory. However, Moloch never takes the promise seriously. In the Modern era, after Crane, Abbie and Irving captured and imprisoned the Headless Horseman, Moloch forced Andy Brooks to hide the Thracian Phiale, which the Hessians burgled from Jesse Adams, inside Brooks’ body. While the Headless Horseman and Brooks was both in captive, Moloch ordered at least seven Hessian troops to blow up the Sleepy Hollow West Power Grid, causing a massive blackout and shut down the UV lights that weakened the Death in process. With the lights shut down, the Headless Horseman regained his power. After that, Moloch forced Brooks to take out the Phiale and then broke the hex of the cell. This unleashed several demon troops, as well as making the Horseman broke free and escaped unharmed.
 * "Sanctuary": In the past, Moloch sent the Tree Monster to the Fredericks Manor, the sanctuary where a pregnant Katrina hid as she gave the birth of her son. Katrina fled safely with her friends’ help. However, due to the protection hex of the manor had broken since Jeremy Crane’s birth, the Fredericks Manor now is no longer a safe place but just a haunted house and a center of dark arts controlled by first tree monster and then Jeremy Crane.
 * "The Golem": At the Christmas Eve, Moloch summons Ichabod Crane to Purgatory, and then he prophesizes the Horseman of War’s arrival before threatening Crane to bring Abbie Mills’ soul to him. This reveals the reason that Moloch forbids the Horseman of Death to kill Crane.
 * "The Indispensible Man": Moloch turns Andy into a mindless demon. He also plans to let Ichabod finds the map that Washington protected, in order to make himself descend on Earth.
 * "Bad Blood": In the past, he summoned Jeremy Crane buried beneath the ground and made him the Horseman of War. In order to prevent something went wrong, he brushed off Mills sisters' memories and locked it in the Purgatory. In the present, he manipulate the two Witnesses' seperate by trapping one of them in the Purgatory as the price of saving Katrina, which later Abbie was forced to do that.
 * Season 2:
 * "This is War": Moloch summoned the demonic souls from the Purgatory and was ready for his ride as soon as the Hessians used the Ghenna Key to open the gate of the Purgatory.
 * "Root of All Evil": Lori Roberts’ last diaries implied that the demons lead by Moloch were tormenting her and hunting her daughters. Abbie said her mother fell into Moloch’s hand and so she committed suicide tragically.
 * "Go where I Send Thee…": Moloch summoned the Pied Piper from death, and so he was responsible for the Piper’s heinous curse against the Lancaster family.
 * "Weeping Lady": Moloch furiously scolds and punches Henry for making Katrina’s life in risk, for she is one of the Hellfire Shards, a chosen vessel. Henry explains that the Weeping Lady did not meant to harm Katrina and this plan is just for pleasing Moloch, yet Moloch coldly says Henry had no rights to plan or think for himself. He then states that Henry is just a soldier with only one duty - obey.
 * "Heartless": With Henry’s help, Moloch’s energy has transported into a glass bottle. He eats the human soul as energy that the Succubus collected for him to take his baby form. In order to feed Moloch, the Succubus had to attack at least four people (including Ichabod and Hawley) in one night, killing at least two.
 * "Mama": More than a decade ago, Moloch sent the ghost of Gina Lambert and let her to capture Mills sisters. The sisters’ mother, Lori Mills, were trying to protect and save her children from the demon. In the present day, in his baby form, Moloch takes some of Katrina’s power by sending her the breath of demons when Katrina hugs him without noticing the baby is in fact Moloch. With Katrina’s power, the demon grows rapidly towards his fully form.
 * "The Akeda": Moloch, who managed to take his fully form, burns down the first two white trees to bring lightings and blood hails down to the town. After burning down the third tree, he summons his demon troops to roam the earth. Later, Moloch orders Henry to capture the Witnesses and their allies as soon as possible, even knowing Henry had his Horseman armor destroyed and in a vulnerable state and will die under the Sword of Methuselah. Moloch even states that there were Horsemen before Henry and there will be new Horsemen after him. After Henry captures Ichabod, Abbie, Katrina and Jenny, Moloch orders Henry to destroy Katrina and burn down the fourth tree, even knowing he WILL break his promise to Abraham of bringing Katrina to him. He coldly reveals that both Henry and Abraham are meaningless to him. Moloch’s words make Henry to see the demon’s true nature, and soon Henry stabs Moloch to death with the Sword of Methuselah. Forcing Henry to fight to his death and slaying Katrina without concerning Abraham is the WORST atrocity Moloch had ever committed, thus pushing him inside a deep dark hole without salvation once and for all.
 * "Posthumous": Moloch was possibly binded himself to the whole Purgatory, for his death triggered the Purgatory's turbulance, causing numerous evil spirits inside it escaped - including demons who were planning to unleash perhaps another Demon King for them to serve, the angel Orion who demanded genocide and almost suceeded, and Solomon Kent who is the key influence to Katrina's fall from grace. Then, even after Moloch's demise, the lives of millions of people around the world is still now at stake.
 * Headless Horseman: He steals a white horse as his new ride and kills the horse’s former owner, yet his first action to cross MEH is which he brutally chops down Sheriff Corbin’s head right after that. After having himself and Crane’s blood tie destroyed by Henry, the Headless Horseman was free to slaughter and then he immediately beheaded 4 Freemasonry leaders of Sleepy Hollow.
 * In "Tempus Fugit", he and a darkened Katrina Crane who travelled to the past planned to destroy Ichabod. The Horseman beheaded Benjamin Franklin and caused Abbie in the jail once again.
 * Jeremy Crane: After he reveals his identity as both the Horseman of War and Jeremy Crane, Henry hands Katrina to the Headless Horseman and buries Ichabod in the coffin where he laid for two centuries. Later, he claims Frank Irving's soul.
 * Sir Banastre Tarleton: He is a sadistic and twisted torturer who is fond of hanging and killing people (espeacially if the implication is there a traitor) without any mercy and regret. Furthermore, he secretly stalked Ichabod Crane and then brutally crossed the MEH when shot down Arthur Bernard, who Ichabod just spared, to die. Then, he angrily regards Ichabod as a traitor just before his transformation to his real demonic form, making all of his words against treachery became some sort of ironies.
 * Ancitif: While possessing Luke, Ancitif lets Devon brushing off all of the salts that Father Boland spread in front of the door and then kills Devon by snapping his neck. After taking control of Macey Irving, Ancitif beats Luke unconscious and leaves him to die. One vital thing is, both Luke and Devon were Ancitif’s former vessels, and yet Ancitif mercilessly attacked them both as soon as they were useless for him.
 * Pied Piper: The Piper made deals with the devil and slaughtered many people in brutal ways. For revenging Daniel Lancaster’s betrayal, the Piper kidnapped Lancaster children when they had their ten-year-old birthday by luring them into his lair using his magic flute. He froze or starved the children to death and used their bones to make his new flute. However, what makes the Piper a heinous complete monster is the sadistic choice he gave to Lancaster parents—if the kidnapped child survived or saved by someone else, other children in the family would fall ill and die in one day.
 * Mary Wells: After being returned from death as the Weeping Lady, she drowned Caroline from the jealousy of her friendship with Ichabod. She later attacked Abbie and nearly killed her. Then, Mary attacked Katrina after learning she is still alive and well.
 * Gina Lambert: In her human life, Lambert drove 51 patients to suicide and was executed. After becoming a ghost by Moloch, she hunted down Mills sisters under her master’s orders. Soon after, she let Lori Roberts takes two mental pills and drove her suicide. Soon, she plans a serial suicide among the patients of the Tarrytown psych.
 * Orion: He triggered the Mt. Vesuvius' eruption and destroyed Pompeii. He was also the mastermind of many disasters. He wants to purge the sin of humanity so he starts his genocide again and again.
 * Katrina Crane: During her plot in a fit of rage to kill Ichabod for revenge, Katrina killed at least two people to ensure her plan secure, and she is also responsible for Franklin's premature death. After her failure, she attempted to strangle Abbie to her death.
 * Conquest: He was responsible for the deathly plague of the lost colony of Roanoke. In present day, in order to free himself, the Horseman made the ghost of an infected child from the colony running into Sleepy Hollow, bringing plague to the town.

Star Wars literature

 * Lumiya: She turned Jacen Solo on the Dark Side and trained him as Darth Caedus.
 * Darth Caedus: He turned on the Dark side and murdered his aunt Mara Jade Skywalker. In an interesting fact, Caedus' means to crossed Moral Event Horizon was mirrored his composite Kylo Ren's own crossing that involved turned to the Dark Side and murder of one's own family member, though in Ren's case, he killed his father (Han Solo) instead.
 * Thrawn: During his military campaigns and conquered half of the galaxy and committed countless genocides.
 * Yuuzhan Vong: They conquered half of the galaxy and deformed many planets like Curuscant or destroyed like Ithor, killing 365 trillion sentient beings and devastated 20 planets.
 * Shimrra Jamaane: He was the Supreme Overlord who lead the war, which resulting him crosses MEH.
 * Onimi: He manipulated king of Yuuzhan Vong to lead a war with the galaxy, which kickstarted the king's own crossing.

Shakespeare's works

 * Iago (Othello): Convincing Othello that his wife Desdemona was cheating on him behind his back, thus convincing him to kill her.
 * Lady Macbeth: She convinced her husband to kill king Duncan.
 * Macbeth: Crosses it when he committed a regicide of King Duncan to take his place.

Harry Potter literature

 * Lord Voldemort: It is said he was evil from the start, as J. K. Rowling has said before the Deathly Hallows came out, and that he was the only character who had no chance of redemption (despite Umbridge, Bellatrix, Greyback, Wormtail, and Crabbe (Goyle in the film), also crossing the Moral Event Horizon in their respective cases that can be seen below). In Half-Blood Prince, it is explained that the reason he turned to the dark side (or rather already there by the time of his birth) was due to his lack of love, something that his mother had not given to him before her death (even his conception was a result of a love potion or imperius curse, which can only imitate love). This practically made him live on a cursed life as a horrifying abomination/monster whose nature was the complete opposite of Harry's in some ways (for instance, Harry's mother-Lily-shielded Harry before her demise. Voldemort's mother, Merope, chose to die rather than raise him herself (although Merope may not have had a choice or supposedly had a chance to do otherwise, as she died a mere hour after giving birth to Voldemort). His known act of MEH crossings since his young age are:
 * Using his newfound magic to tortured 2 children in a cave and kill somebody's pet rabbit at a young age.
 * Creating his Horcruxes out of murders where when he created 3 of them, he framed those who are related with both his victims and objects that he converted to hide his tracks (namely Hagrid, Morfin, and the house-elf Hokey).
 * Murdered Harry Potter's parents.
 * Had Wormtail kill Cedric.
 * Wiping out unspecified numbers of innocent people to create an army of Inferi out of them.
 * Dolores Umbridge: Crosses it by sending Muggle Borns to Azkaban and threatening them with the Dementor's Kiss if they resist. It may have been before that, when she sicced 2 Dementors on Harry and his muggle cousin Dudley Dursley, forced him to write lines with a Blood Quill, attacked Hedwig for his mail, threatened to use Veritaserum on him, and threatened to use the Cruciatus Curse on him.
 * Peter Pettigrew: Crosses it by betraying James, Lily, and Harry Potter to Lord Voldemort and subsequently killing twelve Muggles at once via blasting curse and framing Sirius Black for these crimes immediately after betraying the Order of Phoenix. He crosses this again by killing Cedric and helping Lord Voldemort return to power. He did those things out of fear rather than loyalty to Voldemort, but these acts still make him despicable to the point where he can't be redeemed even though he does show a small amount of mercy when he remembers the life debt he owes Harry Potter.
 * Bellatrix Lestrange: Crosses it by torturing Neville's parents into insanity and killing Sirius only moments before his innocence was proven. She arguably became a Complete Monster by brutally torturing Hermione (which proved to be a fatal mistake as it led Hermione to steal a strand of her hair to use her appearance to infiltrate Gringgots Bank) and killing Dobby. She also tried to kill Ginny with the killing curse during the Battle of Hogwarts, which failed and led to her downfall at hands of Molly.
 * Fenrir Greyback: He was immediately established as a dark character when he is introduced in the series. He could have first crossed it when he bit Remus Lupin or more likely the first time he bit or killed a child. He definitely crossed it when he threatened to kill and eat Hermione Granger when she was being tortured by Bellatrix.
 * Vincent Crabbe: Tries to kill Hermione with Avada Kedavra in Deathly Hallows (which misses and incites Ron's fury in process), and later tries to incinerate the trio with Fiendfyre, which ironically ends up killing only him and even helps the trio by destroying the Horcrux they were looking for at the time.
 * Barty Crouch Jr.: He crosses it by taking part of the torture of Neville's parents, although it was never officially confirmed that he was involved it was most likely that he was since he was associated with the Death Eaters at the time (however, in the movie, it was confirmed that he was involved). He crosses it again by torturing spider in front of Neville, reminding him of his parents suffering, and then crosses it by killing his father. Also, he tries to kill Harry Potter after his escape from graveyard.
 * Gilderoy Lockhart: Tries to erase Harry and Ron's memories while they're in the Chamber of Secrets, which would have prevented them from rescuing Ginny and getting out of the Chamber alive. Fortunately, this backfires due to him used Ron's damaged wand to do so and ironically erased his own memory.
 * Lucius Malfoy: He treated his house elf Dobby with extreme malice and cruelty. He also plants Tom Riddle's Diary in Ginny's book bag, intending for it to work dark magic through her and revive Voldemort. In the movie, he even tries to kill Harry Potter, but is fortunately stopped by Dobby.
 * Marvolo Gaunt: Mistreated his daughter Merope as well as mercilessly attacking aurors, whom attempted to arrest them for an attack on the Riddle family.
 * Morphin Gaunt: Attacked Tom Riddle Sr. by covering him in hives remorselessly just because his sister, Merope, was in love with Tom. He also attacked Bob Ogden and the other aurors who were attempting to arrest him.

Hunger Games

 * President Coriolanus Snow: President Snow is responsible for a series of atrocities throughout the majority of the Hunger Games series. The list is quite long, but he goes so far as to force the children of Panem to participate in the Hunger Games, murder almost all of Katniss's friends and family, and turn Peeta against her. Snow even makes it clear to Katniss that he will take away the people she loves. He also kills Cinna for making a Mockingjay costume.
 * President Alma Coin: Having Prim and many other children killed and trying to start a new Hunger Games.
 * Cato: Killing other careers when he finds them no longer useful.

Twilight

 * Aro: In his backstory, he had his sister killed.
 * Victoria: Creates an entire army of vampires for the soul purpose of killing Bella.

Hercule Poroit

 * Franklin Clarke: Framing Alexander Bonaparte Cust for his serial murder and attempted to got away with money.
 * Stephen Norton: He is a social predator who toys with people's fears, nudging them towards committing murder, while technically never breaking the law himself.
 * Micheal Garfield: He attempted to kill Miranda Butler.
 * Big Four: In original stories of Agatha Christie, they were members of a conspiracy organization in order to range war upon the world. They committed terrorist attack and murders, and they even set up a evil plot to destroy Poirot once and for all. No. 4 (Claud Darrell) set an explosion, which knocked down Hastings and killed Poirot (yet Poirot was later revealed to be survived).
 * However, in the TV series, the whole insane plot was solely set by No.4, Claud Darrell (real name whose real name is Albert Whalley, and whose most prominent disguise in the adaptation is that of Paynter's physician, Dr Quentin), while the rest three "members" were all pacifists under Darrell's incrimination and brainwashing. Darrell is a a brilliant but insane character actor who orchestrates the entire Big Four setup, feeding the press with sensational clues and threatening letters and killing his victims to implicate the Peace Party members (whom he then kidnaps and drugs with immobilizing Gelsemine) thus validating the organisation's existence. His motive in doing all of this is to attract the admiration of Flossie Monro, who becomes an unrequited lover whom he showers with anonymous gifts and cards expressing his love for her. It transpires that Flossie told him he wasn't good enough for her in the past, and the mad scheme is an attempt to make himself the international celebrity he believes she desires.

Stephen King

 * Randall Flagg: His attempts to plunge the world into chaos qualifies. In The Stand he plans to destroy the town of Boulder so his empire in Las Vegas can thrive. In Eye of the Dragon, he kills a king and traumatizes his heir into making him the adviser.
 * Chris Hargensen: In retaliation for her own humiliation, she douses Carrie White in pig's blood and kills her prom king, which results in the town's destruction and hundreds of deaths including her own. Her action turned her into a mass-murderer.
 * Carrie White: In an act of vengence, Carrie locks everyone inside the auditorium and turns on the sprinkler system to wet everyone and ruin their good prom outfits and nice hairdos. What seems to be just innocent fun to Carrie, wetting eveyone, the sprinklers water gets to close to all the electrical cords on the stage. Carrie looks in through the windows of the gymnasium doors and smiles as she sees everyone inside panicking as sparks fly everywhere and people are getting electrocuted one by one as the basketball ball court begins to flood, leaving no one safe from being electrified. Carrie even laughs when one female student is electrocuted and her body moves like a crazed puppet as volts of electricity dance through her body. Students are still desperately trying to open the doors and even looking back at Carrie through the thick glass. As the school building quickly catches fire and spreads. Even so, she didn't crossed this out of malice, but rather provoked by Chris Hargensen to do so.
 * Henry Bowers: Crossed when he kills Mike Halon's dog.
 * Jim Rennie: Amidst his ruthless attempts to control his town, while he was continuously making meth, he sets up a large explosion that destroys said town.
 * Andre Linoge: Stealing Ralph Anderson, Sheriff Mike Anderson's youngest son to be his only heir to his dark magical powers and his vast knowledge of history.
 * The Crimson King: While he is already evil and insane, he arguably crossed it in Black House when he has a serial killer murder children that had the potential to serve as "Breakers". In Insomnia, he masterminds an attempted terror attack on the Derry Civic Center to kill one person, even knowing 2000 people will be killed in the crossfire. Although the attack failed, 70 people were still killed. *Norman Daniels: Crosses it with his horrific treatment of his wife Rose, such as making her miscarry and breaking her nose because she accidentally spilled tea on him.
 * Annie Wilkes: Breaking Paul Sheldon's legs and murdering a police officer. Earlier, it was shown in a scrapbook that she killed over 30 patients as a nurse, including healthy babies.
 * Margaret White: She had been abusing her for years, but she finally crosses it when she attempts to murder her daughter Carrie. She manages to stab her and the wound kills her soon afterwards.
 * Warden Samuel Norton: In the film, he has Tommy murdered for agreeing to testify in court which would give Andy DuFresne a chance to be freed from prison, so Andy can keep doing his money laundering (though in the book, he had Tommy transferred to another prison to keep him quiet).
 * Percy Wetmore: Rigging an execution by giving a prisoner a dry sponge on the electric chair to get him roasted alive, which humiliates and irritates Paul Edgecomb and the other officers.
 * It: Kills Bill Denborough's younger brother, Georgie, one of It's countless victims.
 * Upson Pratt: He crossed it when he enjoys at driving a business rival to suicide.
 * Nathan Grantham: He crosses it by having Bedlia's fiancé Yarbro, her chance for happiness away from him, killed so he could keep her under his thumb.
 * Atropos: As he took on the form of a young girl whose lifeline he had recently cut.

Hannibal

 * Vladis Grutas: Crossed it when cannibalizing Mischa, which is his worst act because it caused Hannibal Lecter's eternal pain throughout his life, even after Hannibal killed Grutas.
 * Mason Verger: Crossed it when raping his sister Margot.
 * Francis Dolarhyde: Crossed it when burning Freddy Lounds alive.

Animorphs

 * Esplin 9466: Famously killed Elfangor and led Yeerk invade countless planets and enslave it's inhabitants.
 * 9466 Lesser|Esplin 9466 Lesser]: In retaliation of having his twin brother (who became Visser Three) banished him for his unhealthy power hunger that warned by his actions in ascended his lowly host Joe Bob Fernestre into a billionaire, household name, and a vast information network that very important for Yeerk Empire's invasion, he uses his created Internet Service Provider Web Access America, as means to hunt down random Controllers so he could killed and devour Yeerk inside them via his host's digestive system as means to sustain himself.
 * David: Silently murdered Saddler, Jake and Rachel's cousin in cold blood so he could use his his DNA to disguised as the latter simply to regain his crippled normal life. This also reveals that his statement where he won't kill any humans was a mere taunt to Animorphs. He even goes so far in killing nothlit Animorph Tobias(whom used to be human but has break the law in morphing that resulting having body of red-tailed hawk) to mark his fall from grace, though it's turned out that he has unknowingly killed a random red-talied hawk whilst the real Tobias was lost his track on him.

Others

 * Fernand Mondego (The Count of Monte Cristo): out of his love rivalry and envy, Fernand crossed the Moral Event Horizon, when he betrayed Edmond Dantes and framed him in treachery, what resulted in losing 14 years of his life in the worst prison in France.
 * Livia of Robert Graves' I Claudius can justify every one of her murders until she is finally forced to kill her husband Augustus. After Augustus' murder Livia stops putting on airs of misunderstood nobility and just views herself as an irredeemable monster.
 * Assef: Beats up and rapes Hassan in The Kite Runner.
 * Lister's Other Self: Shoots Lister's groin with a radiation gun, turning him sterile and thus unable to restore the human race.
 * Golo'Mekk vas Usela: He sold his own people to the Collectors and decided to spy for Cerberus, he was also beating a small human girl.
 * Count Olaf: He abused the Baudelaire orphans, tried to kill them on occasion, and hunted them and killed their guardians to steal their inheritance.
 * Shruikan and Galbatorix: Killed countless dragons and riders, nearly put an end of age of dragon riders.
 * Sgorr: Kidnapped and killed a human baby believing he could gain humanity's power, killed Rannoch's father, killed countless Deer and other animals who opposes him.
 * Mr. Hyde: Hyde's truly evil nature first makes itself apparent when he trampled a small child who had bumped into him in the street. About a year after that, something worse occured. Hyde, without provocation, savagely beat an old man named Sir Danvers Carew to death.
 * Frankenstein's Monster: The Monster sets fire to the cottage and determines to seek his revenge on Frankenstein. The monster also ends up killing Frankenstiein's bride and best friend.
 * Dracula: He demonstrates his malicious and selfish nature by even killing his servant Renfield, who tried to protect Wilhelmina "Mina" Murray out of gratitude for her kindness.