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Abraham Simpson: "Take the art if you want, just don't hurt the boy!"
Mr. Burns: "Oh, I'd rather do both!"
The Simpsons, "Curse of the Flying Hellfish"

  • The Simpsons has "Curse of the Flying Hellfish", where it's revealed that Mr. Burns and Abraham Simpson are the last two surviving members of their unit from World War II, and that the last surviving member will get a case full of old paintings stolen from German homes during the war. When Burns tries to have Abraham killed, Bart convinces Abraham to get the case before Burns can take it for himself. When they actually arrive at the location of the case, Burns shows up too and takes the paintings at gunpoint. When Bart calls Burns a coward and an embarrassment to the Flying Hellfish name, Burns points the gun at Bart's head. Abraham says Burns can take the paintings so long as he does not hurt the boy. Burns says he would rather do both, and then kicks Bart into the empty case hard enough to send the case falling into the water, and then boats away saying "So long, Sarge! See you at the reunion in November!". In other words, Burns attempts to drown a child (even though he could have taken the art without doing so) for no apparent reason other than that the child insulted him. It's thus satisfying as hell when Abraham corners Burns and causes him to have a Villainous Breakdown...
    • Also, in an earlier The Simpsons episode, "The Crepes of Wrath", Bart is treated like a slave by two nasty winemakers in France. At first, this is amusing as we see Bart get what's coming to him for his brattiness. However, it stops being funny when you see Bart sleeping with nothing more than a sack after reading a letter from his mother as the abuse he is suffering begins to sink in. When the winemakers finally force Bart to drink wine laced with antifreeze, putting him in real danger of being killed or blinded, the louts sail over the MEH and all your sympathy goes to the boy, which makes his eventual escape and revenge all so sweet.
    • Sideshow Bob has tried to kill Bart in all of his appearances since "Cape Feare", but he finally crosses the line when he decides to get people to hate Bart while he's on trial, fake his death and, with help from his whole family, burn Bart alive in a coffin being pushed into a furnace. Fortunately, he is caught and, along with the rest of his family, is sentenced to 87 years in prison.
      • It can be argued that Bob had already crossed it in his second appearance. While him framing Krusty the Clown for armed robbery can be justified as him finally having enough of being Krusty's perennial punching bag as well as the TV clown's lowbrow humor, his second appearance has him use Aunt Selma as a "get-out-of-jail" ticket and then cutting off the loose end by murdering her on their honeymoon. Unlike Krusty, Selma hadn't done a single thing wrong to him and was just a lonely, if abrasive, woman. And this was before he tried to kill Bart, who he at least had a reason to hold a grudge against.
    • The entire town of Springfield (except for Homer, Marge, Lisa, Maggie, Grampa and Milhouse) crosses it in "The Boys of Bummer" when they drive Bart to attempt suicide by jumping off a water tower - simply because he cost the Springfield Isotots the Little League World Series by missing a flyball. The fact that, other than Marge verbally tearing them a new one, they ultimately get off scot-free for their deplorable actions only makes it worse.
      • Joe LaBoot and Chief Wiggum are especially nasty; the former for encouraging everyone in town to push Bart over the Despair Event Horizon when he finds out who he is, and the latter for goading Bart into jumping off the water tower.
    • The pre-school teacher's treatment of Bart, as seen in "Lisa's Sax". THIS IS THE REASON why Bart is Bart today. What makes it worse is that Bart was just five years old and her actions made Bart actually consider suicide. Until the aforementioned "Boys of Bummer", this was probably the worst line-crossing moment in the series.
  • South Park: Cartman went over it with "the chili incident" from "Scott Tenorman Must Die", as part of his Evil Plan against Scott Tenorman. He's done lots of evil things since, varying in their badness, but this was pretty much where most viewers decided that it was no longer in-character for him to perform an act of selflessness, and many others decided that he is and always will be a complete and utter sociopath.
    • An example of crossing the horizon without being a Complete Monster is Butters' parents in "Jared Has Aides". After they both beat their son at the same time (and from the sounds of it, the event was pretty savage), it was generally agreed that they are, while not certifiably evil, not good parents. This opinion didn't change even after the episode "My Future Self And Me" when they promised never to beat him again.
  • Danny Phantom played it oddly straight with Danny's alternate future. The whole "Dark Danny creation" scene was flat-out Nightmare Fuel and it even horrified Vlad, which really says something. Case in point, Dark Danny's first appearance where he kills multiple people on screen. Ax Crazy, indeed.
  • Batman Beyond: The Return of the Joker gives the Clown Prince of Crime a rather infamous line-crossing moment: torturing Tim Drake/Robin to insanity and turning him into "Lil' Joker".
    • Even for the Joker, the events of Return of the Joker was extreme. He was already dangerous and psychopathic, but the very nature of how he did it turned him into someone that had to be destroyed as far as DCAU is concerned. Not even Harley Quinn gets a get-out-free card after helping with that. Although she survives somehow anyways.
      • Even Mark Hamill, who had been voicing the Joker for years at this point, felt uncomfortable with the role this time due to scenes like this.
        • Long before that, there was his serial murder spree (complete with victim photos) using laughing gas in one of the earlier Batman: The Animated Series episodes.
    • The Batman has their version of the Joker cross the line when he tries to fling his newly-acquired sidekick into a vat of acid in an attempt to turn him into Joker's mini-me, and admitting that since this acid's properties might be different than the one he fell into, it'll probably just kill him.
  • In Season 4 of Winx Club, Ogron, the leader of the Wizards of the Black Circle, recently got to this dreaded point of no return. After the Wizards pull their I Surrender, Suckers plan on the Earth fairies, Ogron tears open a portal to a nightmarish dimension to imprison all the fairies there. Layla's boyfriend Nabu does an Heroic Sacrifice to close the dimensional gap, but loses his life in the process... and when the Winx try to use the Gift of Life to bring Nabu back, Ogron snatches it and casually casts it away, laughing all the while. This single act caused the distraught Layla to finally snap and join forces with Nebula and the Fairies of Revenge, and marked the point where the Wizards of the Black Circle sunk to a low no other Winx Club villain has ever reached before or since.
    • The Trix also cross the line several times. Darcy crosses it when she attempts to murder Musa for liking the same guy (who incidentally, Darcy didn't really love but at best viewed him as a boy toy), Icy crosses it when she tries to murder Bloom's parents in a twisted Batman Gambit designed to weaken her (which works) before cruelly revealing her true origins and joining her sister in a needless No-Holds-Barred Beatdown on Bloom before taking her powers, and Stormy crosses it when she tries to murder Musa's father just because Musa beat her with a raindance.
  • Teenage Mutant Ninja Turtles
    • While the Shredder has always been the closest thing Teenage Mutant Ninja Turtles (2003) has to a Complete Monster, his personal Moral Event Horizon comes in the episode "Mission of Gravity", when he orders his lieutenants to steal the Triceraton engine holding the city of Beijing aloft miles above the earth, despite the fact that doing so would naturally doom the millions trapped within it. It was possible to remove the engine without killing anyone, but he didn't care.
    • In an example of crossing the Moral Event Horizon without becoming a Complete Monster, when Leonardo saves Karai from falling her to her death, she stabs him from behind with his own katana when he would have let her go in the spaceship anyway. This is one of the things that leads him to tell her she is just as bad as the Shredder. It can be argued that every decent thing she did after that was just self-preservation.
    • The original series had Shredder cross it by blowing up the Channel Six building. He earlier exposed April to the lethal fumes of the Doku plant.
    • In the Nickelodeon series, a few villains have pulled it off:
      • Newtralizer crosses this by engaging in a speciesist murder spree against innocent Utroms, stealing New York's electricity and disintegrating Michelangelo.
      • Shredder has several, but his most definitive one is murdering Splinter in cold blood.
  • Phineas and Ferb
  • While very rare on Kim Possible, it could be said that Drakken touched upon it when he created a synthodrone to mess with Kim's feelings.
    • Monkey Fist played it even straighter in the fourth season. Attempting to murder and/or kidnap a child is bad enough, but he made a Deal with the Devil, or rather, a demonic monkey being in order to command it. Some could say that his Taken for Granite death was well deserved.
  • In the first season finale of Avatar: The Last Airbender, Admiral Zhao crosses this when he kills the Moon Spirit, purely to spite Iroh and Aang. It hadn't even done anything to him: he simply wanted to make a name for himself so that he would be remembered by history forever, but as Iroh told him "History isn't always kind to its subjects". Iroh is ultimately proven right, as the Ocean Spirit goes apeshit and drags Zhao off to the Spirit World where he'll suffer for all of eternity.
    • It's made worse by the fact that Zhao hesitates when Iroh tells him to let the spirit go, and then he does let it go... only to then kill it anyway!
    • Azula shooting Aang in the back with lightning and almost killing him in the season 2 finale is either her Moral Event Horizon, her Moment of Awesome or both. On the one hand, she'd be stupid not to do it, since this is an important battle in a war and all. On the other hand, the sadistic pleasure she clearly took in it was rather unnecessary. But then again, it IS Azula.
    • Fire Lord Ozai started at this and just kept running. After his son disrespected one of his generals in the war room, he burned part of his face off and sent him on a Snipe Hunt. When Zuko mouthed off to him years later, he tried to kill him with lightning. Still, villains have been redeemed from worse. What truly defines him as a Complete Monster is his utter excitement at carrying out his plan in the finale, which is to quell the rebellion in the Earth Kingdom by burning the entire continent to the ground.
      • He gets one of these moments earlier in the finale, too. Azula had been completely loyal to him, and even helped him think up his current plan by suggesting burning the Earth Kingdom land to end a revolt (which he naturally expanded into a Kill'Em All deal.) He then rewards her by promoting her to Fire Lord... right before promoting himself to Phoenix King, rendering the position of Fire Lord entirely meaningless. It's entirely clear that he intended this to be an as-cruel-as-possible You Have Outlived Your Usefulness. She gets the position she's always wanted... and is rendered completely impotent for it.
    • Moral Event Horizon crossing seems to have been a family trait since Sozin's day: Sozin stabbed his best friend Roku in the back (though at least he seems to slightly regret it in the end) and ordered the annihilation of the Air Nomads, and Azulon would only allow Ozai to become the heir if Ozai killed his only son Zuko, as "punishment" for Ozai mocking the death of Iroh's son. Zuko could have easily become just like that if it weren't for the guidance of Iroh.
    • And let's not forget Long Feng, the Earth Kingdom's Evil Chancellor, who brainwashes and then KILLS Jet, a teenage boy, in cold blood.
    • Hama has every reason to be sympathetic: she was stolen from her tribe, kept locked up in a prison that took every precaution to prevent her from bending, and kept there for decades. In fact, she uses this information to garner Katara's sympathy, then reveals that she escaped by bending the blood in the bodies of the guards, and is now using this same power to herd innocent civilians to a mountain where she keeps them prisoner out of blind revenge. And then she tries to forcibly teach Katara the technique, and sends her into an Heroic BSOD by using her bloodbending power to manipulate Aang and Sokka into fighting a panicking Katara. She serves as a reminder that even the most innocent people in a war can become no better than those who persecute them if pushed far enough.
    • In Sequel Series The Legend of Korra episode "When Extremes Meet", Councilman Tarrlok crosses it when he captures civilian non-benders on Equalist suspicions, arrests the new Team Avatar for trying to help them, and to top all off, bloodbends Korra and has her exiled from Republic City to a mountain retreat where he locks her up in a metal box, hoping she'll never be found.
    • The first Big Bad, Amon, crosses it when he threatens to take away the bending of Tenzin and his children, thus making airbenders extinct all over again.
    • Yakone did it when he bloodbended an entire courtroom of people, and then afterwards attempted to use his bloodbending to snap Avatar Aang's neck, slowly and painfully, all with sadistic joy. If this didn't put him over the line, then the abuse of his two young sons (including ordering them to bloodbend each other and preparing to assault the younger son when he refuses) definitely did.
    • Hiroshi Sato comes to not only reject his own daughter due to his hatred of the benders she's siding with, he actually tries to kill her for it! Needless to say, Bolin is quite right to call him a "terrible father", something Asami sadly agrees with.
    • In Beginnings, we meet Vaatu, spirit of chaos and all around God Of Evil. His moment is when he corrupts Wan's spirit friends into dark spirits and causes a fight between them and Wan's human friends. Wan tries to stop the two forces, but he isn't a full Avatar yet and the strain knocks him out. When he comes to, he finds the valley in flames and Vaatu gloating about how all of Wan's human friends had been completely slaughtered.
    • Chief Unalaq, the second Big Bad, crossed it at lightning speed when he threatened to destroy the soul of Jinora, who's just a pre-teen girl...and then very nearly did it. And this is before we learn that his plan is to merge with Vaatu to become a Dark Avatar who can destroy the entire world, cast it into darkness, and rule over it as the spiritual ruler of everything that exists!
      • Think that's not bad enough? How 'bout killing the Avatar spirit itself, breaking all of Korra's connections to her past lives permanently? Followed by trying to completely decimate Republic City and kill everyone?
    • Zaheer, the third Big Bad, crosses it in the season finale by giving Korra mercury poisoning so that she can go into the Avatar State and be killed by him and his cohorts, which would end the Avatar cycle forever.
    • Kuvira, the final Big Bad, soared over it when she gave the order to have Zhu Li, who was The Mole in her imperial army dropped in an evacuated town that she was going to have blown up by her spirit-charged superweapon as a test drive. She then proceeds to graft said super weapon to a giant mech suit and threaten Republic City with its power as a show of force so that the entire world would submit to the Earth Empire. And she shows just how dedicated she is to her cause when she risks the life of her fiance, Baatar Beifong Jr., to have a shot at eliminating her enemies.
      • Baatar Jr., meanwhile, crossed the line when he ordered to have his mother, father and brothers all locked up when they refused to bow before Kuvira. He's also the one who actually built the super weapon.
  • Scooby Doo Mystery Inc, surprisingly, had several moments where villains crossed the line into pure evil territory:
    • For Mr. E, or his "associate" Ed Machine (if it was his idea), the Alice May plot, which involved terrorizing, kidnapping and imprisoning an innocent young man for several days, all just to get an old yearbook to the gang.
      • E himself officially crosses it in Season Two when he attempts to have the gang blown up with a bomb in the episode "Scare Bear". Fortunately, he ends his life (in the old reality) coming back from over it via a Heroic Sacrifice.
    • For Mayor Jones, asking the kids to come to the Cicada Festival; he says he has a plan to protect them. He actually wants photos of them being overwhelmed by swarms of bugs for tourism purposes. Consider that one of said kids is his own son.
      • And he gets worse: How about kidnapping a baby from people he knew - people he forced to leave town none the less - and fed him lie after lie as he grew up. Oh, and he's the Freak of Crystal Cove, and thus is the cause of EVERY SINGLE THING that happened to the original and current Mystery Inc.
    • Pericles gets a couple in the finale too. Besides helping Mayor Jones ruin his friends lives for the sake of the treasure, he murders Ed Machine, Mr. E's assistant. Of course, he actually tops himself next season when he murders Cassidy Williams.
      • In the last half of the series, he keeps going and going AND GOING right over the Horizon. Unleashing the horrible herd on Crystal Cove to devour everyone and everything, abusing Ricky to the point of threatening his life, leveling the entire town to the ground in order to force it's citizens into slave labor for him, ordering for every man, woman, and child of the town to be massacred by his robots just to keep them quiet after they'd served their purpose, having his robot gun down Hot Dog Water, a teenage girl, in cold blood, and willingly accepting the Nibiru Entity inside of him so that he can destroy and dominate the world - there were no lengths this psycho parrot would NOT go to in order to get what he wanted!
    • Fred's real parents, Brad and Judy, cross it when they fire a missile at a helicopter that the gang, their son included, are on in an attempt to kill them. And then they rat out Mr. E to Pericles. And then they get plastic surgery so that Brad looks like his own son while Judy looks like an older version of her son's girlfriend as part of a scheme to Mind Rape their son into revealing to them the planispheric disc's location. And if any hope for them to come back over from this remained, they assist Pericles in murdering Hot Dog Water, with no remorse whatsoever. Thank goodness the Brad and Judy of the new reality aren't nearly as depraved.
    • Not only does the Nibiru Entity spend the last episode killing everyone in Crystal Cove as he brings about the apocalypse, but as the one behind the curse, he is the literal black hole that causes the Moral Event Horizon. All the above characters' moments? They can all be absolved because this bastard is the thing that drove them to it!
    • Of course, all of these MEH crossings ultimately ceased to exist in the end.
  • Disney's The Legend of Tarzan has Professor Philander, rival and Evil Counterpart to Professor Porter who has the same goofiness and is generally a Harmless Villain most of the time, commit a downright irredeemable act when he cuts a rope where Tarzan's hanging on, sending him to fall to his apparent death, and then rather then letting his rival check on his son-in-law to tend to his wounds, he orders to have him thrown overboard the boat they're on into the sea. Just to spite Porter.
    • Lt. Colonel Staquait crossed it by ordering Hugo and Hooft to burn a village full of mostly innocent women and children, an order the two men refused to carry out.
  • Dr. Rockso, hitherto one of the most popular characters in Metalocalypse, crossed this when he stole the Christmas presents Toki got for everyone, hocked them for cocaine money, then received a handjob on live television while bragging about his drug addiction, and getting Karma Houdinied because Toki experienced Diabolus Ex Machina before he could beat up Dr. Rockso.
  • At the end of the second season of Re Boot, Megabyte and Hexadecimal team up with Bob to stop the Web Creature invasion. However, near the end of the episode, Megabyte launches Bob into the Web and soon after takes over Mainframe. There was no turning back for him after this.
  • The Ed, Edd 'n' Eddy series, for the last few minutes of it, Eddy's brother crossed this when he began to mercilessly beat the shit out of his little brother, Eddy, and freely admit he's always done this to him.
  • Some - if not all - of the many things that the Justice Lords (counterparts of the Justice League) did in A Better World. Lord Green Lantern, when attacking League Lantern, attempted to slit League Lantern's throat for his first move. Not trying to disarm him or to knock him out. He chose to go immediately for the kill. From the DVD commentary, the writers did that on purpose so that it showed that the Justice Lords, while having good intentions, ultimately are truly villains who deserve to be defeated.
    • In the same episode, Lord Superman had Flash by the neck with Flash trying to appeal to any remaining good in him. Also, keep in mind that the Flash in their world had been killed and his death was one of the main reasons why they all became such cynical Knight Templars. However, Lord Superman coolly told him that "one less Flash in the multiverse wouldn't hurt", that this universe's Flash's death was just another means to an end. This contrasts him with the more-redeemable Lord Batman, who is visibly horrified when he thinks Flash's heart has stopped.
    • A minor villain named John Dee/Dr. Destiny crossed it in the episode "Only A Dream", where he "operated" on his wife in her dreams, torturing her until she died from a fear-induced heart attack, shortly after he had found out that she was planning to leave him for another man.
    • Orm the Ocean Master tried to kill his brother's infant son. His brother did not take it well. At all.
  • Vilgax in Ben 10, after getting a valuable crystal, murders the entire planet for no reason. They weren't doing any harm to him, he fired on the planet for no reason other than to test just how powerful the crystal is, and shows no regrets.
    • Kevin 11, in his debut episode, comes pretty close when he attempted to cause trains filled with innocent people to crash just so he could take their money, but in the sequel series, he ultimately manages to be redeemed. However, the Alternate Timeline episode "Ken 10" reveals that he would have only gotten worse in the future if he hadn't changed. As Kevin 11,000, he attempts to have Ken, Ben 10,000's 10-year-old son, and even his own son killed. For FUN.
    • Ghostfreak crossed it when he possessed Gwen and threatened to make her jump off a building to her death if Ben and Grandpa Max didn't surrender to him. And he did it with a Slasher Smile!
      • He later wanted to plunge Earth into darkness, the result of which is shown to be horrifying mutations of all living things, which is just a side effect of his plan that he didn't even care about.
    • In Ultimate Alien, Aggregor did this onscreen by murdering five innocent aliens in cold blood. However, he could be considered to have already crossed it when he came up with a plan ending with him murdering a newborn.
    • Defying Villain Decay, Zombozo crosses this by forcing Ben's mother to walk a tightrope and then lighting it on fire underneath her, intent on ether burning her alive or sending her falling to her death. This pushes Gwen so far that she assumes her One-Winged Angel form and scares the living crap out of him.
    • Colonel Rozum imprisoning 775 aliens in a horrible underground prison for over five decades, many of whom likely did nothing wrong. Prisoner 775, for example, was exiled to Earth by an alien tyrant who he was trying to save his planet from. He told Rozum this multiple times and they didn't listen. The only thing keeping this guy from being a Complete Monster is his love for his family.
      • Prisoner 775 himself has one. Once he escapes, he intends to exact his revenge against Rozum. A viewer might not condone it, but could certainly understand his reasoning for revenge against just Rozum. Problem is, 775's targets expand to Rozum's whole family. They had absolutely nothing to do with his captivity, and he knows it. He just wants to kill them to make Rozum suffer. This may have been an intentional crossing of this on his part, as in the end he attempts Suicide by Cop, so he may have just wanted to do something that would force Ben to kill him and end his suffering along with getting his vengeance.
    • Charmcaster sacrificing thousands of souls, even killing Ben, Gwen and Kevin, in order to make a Deal with the Devil that will resurrect her dead father. Though to be fair, she does have a My God, What Have I Done? and go into a Villainous BSOD when he calls her out on it, and since this is a series where alien Nazis like the Highbreed can be forgiven...
      • Word of God comments made online actually seem to indicate that this act is, in fact, an INVERSION of the Moral Event Horizon. Instead of being the point where Charmcaster crosses the line into irredeemably evil, her realization of how wrong it was due to her father's words has pushed her completely AWAY from evil, and she is thus now a True Neutral character rather than still a villain. The real Moral Event Horizon here is Diagon, seeing how he's not only responsible for the above action, but it's implied that he's responsible for Charmcaster being corrupted to start with.
    • Captain Nemesis crosses the line in "To Catch a Falling Star" by becoming the first successful hands-on murderer in the series. He kills several people, including a random motorist just to steal his car. Even his Pet the Dog moment at the very end doesn't bring him back across the line.
  • In Captain Planet and the Planeteers, Verminous Skumm crosses the line in almost every episode he appears. His most infamous moments are in episodes "Mind Pollution" and "A Formula For Hate". In the former, he hands out mind-affecting drugs to teenagers, which actually leads to the death of Linka's cousin, who died of a fatal overdose. He did it just for the joy of ruining the lives of the kids and those close to them. In the latter, he harassed a HIV-positive teenager and spread lies about AIDS because the kid was an easy target, planning to use the naivety about AIDS of the townspeople to spread a hatred disease that would get him closer to take over the world.
    • Dr. Blight crossed the line in episode "A Good Bomb is Hard to Find", where she and her future self went back in time to World War II and decided to sell nuclear bombs to HITLER. The Planeteers even say that this is low, even for Blight.
    • Zarm is one nasty work himself for two words: Scorched Earth.
  • In Codename: Kids Next Door, Father attempting to bake a dozen or so children from a tube race into a cake for the Delightful Children. If that didn't put him over the line, then he was already over it due to what he did to Sector Z, who are now permanently brainwashed into being the Delightful Children From Down The Lane.
    • And he's a saint compared to his dad, Grandfather, a vile bastard who wants to transform kids and adults alike all over the world into "senior citi-zombies" and forcing them to labor at factories to make tapioca pudding solely for his own consumption. What sends him over the line is his brutal abuse towards his sons, trying to murder Numbuh Zero (his favourite child, no less) and turning Father into the screwed-up person he is, essentially making Grandfather the being responsible for all the crap that happens in the series. If this doesn't make Grandfather a Complete Monster, nothing else will.
    • Nurse Claiborne was always nastier than the other villains in the series, but she really crosses the line by trying to kill Numbuhs 3 and 5 in cold blood during her second appearance. She tries to shred Numbuh 3 into breakfast cereal, and clearly enjoys it.
    • Chester trying to feed Numbuh 3 to a family of sharks in only his second appearance. To say nothing of his Mind Rape of Numbuh 1, or giving kids Moosebumps just so he can profit off of treating them.
  • As of the second episode of the second season, Archer has implanted a faulty Russian Mind Control chip into the head of Len Trexler, head of ODIN. Even Archer himself feels bad about it, if it has any permanent damaging side effects.
  • Murdoc constantly teetered on the line between Jerkass and Complete Monster, but he finally crossed it when he kidnapped and imprisoned 2D. It wouldn't be quite so bad if not for all the horrific undertones of the drugging, incarceration and physical abuse. Granted, 2D was never the bravest or keenest individual, but he was always pretty harmless. Murdoc's brutality and the constant isolation have all but broken the singer, and it's around that point that Murdoc bridged the Moral Event Horizon.
  • Clay Puppington crossed the line in "Nature: Part 2" the moment he shot Orel, his own son, in the leg. How does he feel about it? No regret. Even if there are two episodes showing of how did he become the bad father to be, there is no sympathy for him now.
  • X-Men: Evolution had one for most of the villains:
    • Avalanche tried to kill Kitty in their first episode after an episode of emotional manipulation, and possibly killed hundreds of students when he destroyed the school. It took a whole season, if not more, to have him portrayed in a somewhat more sympathetic way;
    • Pietro had his when he had a train derailed for the purpose of pretending to save people, and upon finding out that if they fail hundreds will die, including himself, he runs away and leaves those trapped, and potentially the entire town, to die. And keep in mind that he knew his Brotherhood friends and his sister were there, and he left them there anyway.
    • Magneto crossed it when he had his own daughter Wanda Mind Raped, just so she'd stay away from him. Said Mind Rape took place via replacing her memories of him abandoning her in a mental institution, which is what made her become a Dark Magical Girl in the first place, into loving memories that made her forget his abuse;
    • Mystique when she tried to kill the New Recruits, for literally no reason other than them being unable to fight Magneto. And she did it again via kidnapping Scott, stealing his his ruby quartz glasses, and leaving him stranded in the middle of nowhere
    • Apocalypse's was the plot of the finale: to turn everyone into mutants, knowing that most would die in the process due to the nature of it, but not caring because "only the strong should survive".
  • In My Little Pony Friendship Is Magic
    • Discord nearly crossed this in "The Return of Harmony" by corrupting the Mane 6 into his lackeys and bringing chaos throughout the land. In "Keep Calm and Flutter On", Discord claims that he was acting out in self-defense and did so with such glee only because he was Chaotic Evil, so Fluttershy becomes his Morality Pet. In "Twilight's Kingdom", Discord actually touches the line by betraying the ponies, including Fluttershy, in favor of Lord Tirek, but because he gets betrayed by Tirek afterwards and feels remorseful for what he did, he makes a true Heel Face Turn, bringing him back over from the MEH.
    • Imposter Princess Cadence/Queen Chrysalis crossed this by leaving Twilight trapped in the caves under Canterlot, caves that were long forgotten so nopony would ever find her. Then taunting her with that fact! And then it's revealed she did the exact same thing with the real Cadence.
      • And this after letting an already-broken and regretful Twilight think all is forgiven.
    • Lord Tirek crossed it in "Twilight's Kingdom" by sucking the magic out of everypony in Equestria, banishing the Alicorn princesses to Tartarus, and betraying Discord by sucking out his magic once he was sure he'd earned his complete trust. Which is after he'd made a false gesture of friendship by giving Discord a pendant that had previously belonged to Tirek's own brother Scorpan, whom he deems as worthless as the pendant and the concept of friendship itself.
  • In WITCH, you have a number of villains, but one who could easily stand out as crossing the line is Nerissa. Where Prince Phobos was already a Smug Snake, Nerissa started out as a normal woman, no, Guardian. But, she got a little too attached to the Heart of Candracar and was forced to hand it over to her dear friend Cassidy. When Cassidy refused to return it, Nerissa struck her down in a fit of anger. She would spend the next generation plotting Phobos' downfall so she can take over, armed with as many Hearts as possible, going on a dog-kicking spree "for the good of the universe".
  • In Transformers Prime, Megatron almost kills Raf and then gloats about it. He was only attacking Bumblebee at first and may not have known Raf was there, but when he found out what he'd really done, his reaction takes away any fragment of good left in him.
    • An earlier episode has Arcee avert this. She ends up having Starscream on the ground begging for mercy after a fight and then prepares to murder Starscream as an act of vengeance. However, when she sees that Bumblebee is seeing this, she realizes her mistake and lets Starscream go.
  • In the third season of Jem, Eric Raymond crossed it when he destroyed the master tapes to the music of Jacqui Benton, Jerrica's mother.[1] Keep in mind that instead of meeting either Eric's demands (either one million dollars for the tapes or controlling interest in Starlight Music), Jerrica asked that Eric just return them, hoping that there was still some shred of humanity left in him...
  • In Star Wars: The Clone Wars, a Zygerrian slaver wants to make sure Obi-Wan obeys his every command, and he does so by dropping some Togrutan prisoners down a bottomless gorge.
  • Futurama: Zapp Brannigan is a grade-A Jerkass, putting himself above others and commanding suicide missions. However, some may argue that he crossed the line in The Beast With a Billion Backs. Kif dies as a result of trying to go against the Dimensional portal Yivo. After hiding in a shack with Amy and Leela, Zapp begins "reminiscing" about Kif. Zapp then SLEEPS WITH AMY. So, yeah, the jerk literally used a widow's husband's death... to get laid.
    • If he didn't cross it then, Zapp definitely crossed it in "In Gadda Da Leela". Leela and Zapp crash on an unknown planet, alone and without supplies. Leela is trapped under a fallen tree, and delirious from lack of water, and the Earth has apparently been destroyed. Throughout the episode, Zapp appears to be helping Leela get better and displaying genuine Pet the Dog behavior towards her. And then we find out they're actually still on Earth and Zapp has not only been using their current predicament for an Adam and Eve Plot-style seduction, but placed the hazards there in the first place so that he'd have a better shot at sleeping with Leela again! The writers themselves seem to know that what Zapp did was unforgivable since they originally planned for Zapp to get off scot-free, but changed it to Leela punishing him in a rather fitting manner.
  • In Thundercats 2011, the act that cements Mumm-Ra's evil happened in the backstory when, on the behest of the Ancient Spirits of Evil, he destroyed the Plundarr star system which was inhabited by billions to create the metal needed to forge the Sword of Plundarr. It even acted as one in-universe. This heinous act convinced Leo that Mumm-Ra was not the visionary bringer of order to the universe that Leo thought he was but a monster that needed to be stopped.
  • In Adventure Time, the Earl of Lemongrab definitely crossed it in "Too Old". He constantly abuses his clone physically and verbally, attaches shock collars to all of their 'sons' and forces them to entertain him after he becomes a Fat Bastard, and mercilessly eats his twin (again) before ordering their boys to kill Princess Bubblegum, Finn (who's too distracted by his relationship blues to care) and Lemonhope.
    • The Lich crossed it when he killed Billy and Prismo, both of which were done during attempts to end all life in the universe For the Evulz.
  • Courage the Cowardly Dog featured Mad Dog abusing Bunny to the point where he buries her up to her neck in dirt when she tried to escape, and then later trying to drive her and Courage down with his car.
    • Just anything Katz did qualifies as putting him over the horizon.
    • The insane vet who sent Courage's parents to space was well over this too.
    • Eustace was always a Jerkass to begin with, but he crossed it when he gathered up the villains to kill that "stupid dog"... in a dodgeball game!
  • Recess: In the episode "Biggest Trouble Ever", the Recess Gang accidentally breaks the statue of Thaddeus T. Third III, the namesake of Third Street School. For this, they get in trouble not just with the school, but with the entire town, getting labeled "The Destructive Six" and made to work menial jobs by Ms. Finster as a punishment. This seems like just being made to face consequences for their careless actions, but it goes way too far when Mayor Fitzhugh and the City Council decide to send the gang to six separate schools, despite the fact that their crime was an accident and they were genuinely remorseful for having done it! This shocks everybody, as even Prickley and Finster think that this punishment is crossing a line. Luckily, Thaddeus T. Third V (grandson of Thaddeus T. Third III) calls him out on this, even revealing that not only have kids been playing on the statue of his grandfather for ages, but Fitzhugh himself had intentionally tried to break the statue when he was a child! Most of the antagonists in this series are jerks, but Fitzhugh's hypocrisy here was very notable.
    • Dr. Benedict's plan in The Movie involved moving the sun away to have "no more summer". Not only would this suck for kids and grownups everywhere who want summer vacation, but it would've nearly killed all life due to extreme freezing conditions if the sun was rotated far enough!
    • Dr. Slicer, the Nazi replacement principal in "Prickley's Leaving", was already cruel and heartless, but when he demanded the cannon to be functional, he showed his darkest side.
  • Sonic Boom: Shadow proves himself a massive threat no better than Lyric in the second-season finale, where he plots to destroy the entire universe out of a slight against him.
  • Arthur:
    • While the title character's annoying little sister D.W. has always been somewhat of a Jerkass to him, to the point of making an insensitive remark at his expense when his dog Pal got sick, the Season 4 episode "Arthur's Big Hit" has her come dangerously close to being an outright sociopathic Enfante Terrible. At the beginning of the episode, Arthur is trying to build a model airplane throughout the week while D.W. constantly harasses him and he repeatedly tells her not to touch it, but D.W., of course, ignores his warnings, plays with the airplane anyway, and breaks it when she tries to make it fly by throwing it out of his window. That was already bad enough, but her Moral Event Horizon comes in when Arthur confronts her about breaking the plane, and instead of apologizing for what she did, she blames Arthur for building a plane that can't fly, leading Arthur to lose his temper with her and punch her straight in the arm. Afterwards, D.W. goes crying to their parents that Arthur hit her and they punish him with no TV for a week [2], and at school, his friends also ostracize him for hitting his little sister. Later, Binky Barnes is dared to hit Arthur by the other Tough Customers, and even at the end of the episode and after receiving her implied punishment, D.W. still shows a complete Lack of Empathy not only for breaking something Arthur worked on for weeks, still blaming him for building the plane wrong, but also for indirectly causing him to be hit by a bully much bigger and stronger than himself. While getting Arthur hit admittedly wasn't her intention, the fact that she didn't show any empathy for him when it did end up happening indirectly because of her own actions is understandably considered by the viewers to be just downright vile and unforgivable, and the pure evil she shows here renders any good acts she did in any episode before this one meaningless and makes any ones she does in any episode after this one come off as out-of character compared to it. And no, the fact that she's only four years old is definitely not an excuse.
    • Supreme Dog crossed it in the only episode he appeared in, "To Eat or Not to Eat", by distributing Big Boss Bars, which were explicitly said to contain life-threatening ingredients, to children just to make a profit for himself. Fittingly and thankfully, he goes to jail for it at the end of the episode and the Big Boss Bars are permanently recalled from sale.

Notes

  1. Jacqui had died in a plane crash, and they were (at that moment) the only known copies
  2. It is implied that they do punish D.W. for breaking the plane as well, but it's not shown to the audience.
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