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"No one in their right minds would ever confuse Peter and Lois Griffin for Good Parents. But in [Go, Stewie, Go!], they are borderline criminal.
—The Parents Television Council

You think Cartoonish Supervillainy is nothing to worry about? Think again.


Shows with their own pages


  • American Dad!:
    • Roger the alien among us has always been somewhat amoral and sociopathic, but the behavior has been flanderized to an unsettling degree in later seasons. He may have finally crossed the line in the season 8 premiere. He becomes obsessed with Hayley, an obsession which culminates first in his shooting and injuring her then kidnapping her. He takes her to an abandoned warehouse, ties her arms & legs to the posts of an old bed and tells her he PLANS TO SKIN HER ALIVE AND WEAR THE SKIN in order to "be closer" to her. After menacing the struggling Hayley by laying out the various tools he plans to use in front of her, Roger is interrupted by Hayley's husband, Jeff Fisher who finally gets him to listen to reason. Just when it looks like everything is going to be okay, Roger takes Jeff into the bathroom, SKINS HIM ALIVE AND COMES OUT WEARING HIS SKIN thinking it will make Hayley love him as much as she loves Jeff. The episode ends with Roger realizing he's no longer obsessed with the now-horrified Hayley and shows Jeff is still alive and will be getting his skin back, but it's still going to be difficult to erase such a terrifying episode. How would Jeff & Hayley be able to live under the same roof with him ever again?
      • Roger may have crossed it earlier in "Virtual In-Stanity", where he kills five teenagers and brutally hits each with a limousine that he stole, simply because they didn't pay for their trip. What makes it more convincing that he crossed the MEH at this episode was that he neglected a bunch of puppies, destroyed an entire plane with people inside during his revenge streak, killed an innocent flight attendent by taking her parachute for the sake of having blood rush, and stating that has killed teenagers for not paying their fare to him the week before.
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    • Barry, when he is not medicated, crosses this in "With Friends Like Steve's", which takes advantage of the family of Steve and earns the trust of Stan, then he blames Steve for making atrocities for them to go away to a correctional, then tries to kill Stan.
    • Stevearino, Steve's Evil Knock Off is probably the most evil character in the series, to the point where the show doesn't even try to portray his actions as Crossing the Line Twice. His atrocities are not justified and are played very seriously, and include, but are not limited to, the following: Murdered and tortured multiple cats, tried to take over the original Steve's life by kidnapping and stuffing him in a small cage, planning to kill him later, and nearly killed both Stan and Francine when they finally figured out what was going on.
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    • One-time characters Nick and Cassandra, Francine's biological parents, either do this by abandoning her as a baby because babies can't ride first class, or when they wouldn't save Stan from being trapped under a wooden beam in his burning house because they didn't want to become a liability.
    • Emperor Zing, another one time character has crossed this in the only episode he appears in. He humiliated numerous alien slaves in public by showing them memories of the rough patches they went through with their loved ones in public just for the sake of propaganda and deceiving the public while calling the whole ordeal a test and then removing the "tools for love" from such aliens who challenged his belief that love does not exist and he did that test on Jeff. He also forced the Majestic to only show the bad memories of the people who took the "test" and threatened to blow The Majestic into space if he disobeyed and showed the good memories. It is also implied that he tried to kill Roger by sending him to Earth to be a crash test dummy just because Roger cheated on Zing with another man, which could mean that Zing crossed the MEH long before his début.
    • Stan crosses it when he tries to "unclone" a couple of cloned teenage girls that Steve created by killing them so he would not lose his job. He kills one such girl who tried to run away from him, which shocked Francine with Stan telling her not to judge him since she was just a clone. Stan later states in a later episode that he only kills for the sake of protecting others but when he killed that clone, he blatantly committed an act of murder.
      • Stan may have crossed it in an earlier episode but fans have a hard time agreeing on when he crossed it. Such examples include framing Francine for a murder his boss committed just to prevent her from saying "I told you so" to him, kidnapping Greg and Terry's newborn baby out of homophobia and attempting to take her to Nebraska, and then there was this episode where he tries to get an atheist friend of his to become a Christian by intentionally making his life more difficult through getting him into a near death experience, brainwashing his wife into becoming a lesbian resulting in leaving him and taking away his kids, and ruining his business which causes that friend to attempt suicide and end up becoming a Satanist. There was also that scene where Stan kills a co worker of his just because that co worker accidentally caused Francine's face to get ruined in a microwave room.
    • Steve crosses it in the episode where he tries to get revenge on a trio of girls including Lisa Silverman for humiliating Debbie in a school election. It comes when Steve intentionally gives Lisa an STD by stealing her teddy bear, giving it to a hooker to mess around with, and then returning the soiled bear to Lisa while she was sleeping.
  • In American Dragon: Jake Long the Huntsman is presented as evil and devoured by his hate for magical creatures in general and dragons in particular, but he still has a somewhat soft spot for Huntsgirl/Rose. Then we learn he kidnapped her from her parents minutes after she was born. But that's not his MEH; after all he WAS a good Parental Substitute to Rose and gave her a solid set of morals, aside for that hate for dragons she later overcame. No, his MEH is when he finds out of Rose's Heel–Face Turn and reveals he knows where her parents are and threatens to kill them if she doesn't lead him to the Aztec Skulls in the hands of the dragons and fights for him while he activates them. Thankfully, this directly leads to the destruction of the whole Huntsclan at Rose's hands.
  • Walter Wolf, Slappy Squirrel's nemesis in Animaniacs, sinks to the ultimate low in "Rest In Pieces" by faking his own death in order to turn everyone against her, including her nephew!
  • 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 and possibly his father. Even Archer himself feels bad about it, if it has any permanent damaging side effects.
    • Barry's Moral Event Horizon was probably murdering Jakov, another candidate for Archer's father.
    • Major Jakov's Moral Event Horizon probably came in "Dial M For Mother", when he brainwashes Archer to turn him against Malory.
    • Malory crosses the Moral Event Horizon in Season 2 and 3 flashbacks to Sterling's childhood: she got him drunk and taught him to gamble so she could steal his Halloween candy, and berates him for being unable to hold his liquor. She bought him a bike for his birthday, then stole it and punished him for losing it, without even telling him what she'd done.
  • In the Redhill story from Animated Tales of the World , the Adviser crosses this when he orders the guards to kill Nadine and his grandmother, even though he had already successfully convinced the Rajah that he shouldn't take advice from a young boy such as Nadine.
  • Red Skull from The Avengers: Earth's Mightiest Heroes! crosses this in season 2 where we find out that he captured and brainwashed Bucky and turned him into Winter Soldier, an emotionless killing machine and made him commit several atrocities, and did same to Doc Samson and The Falcon. Skull also infected the entire New York city with his Dust of Death, which might have possible killed many innocent civilians, just to discredit Avengers and kill Captain America, while being under guise of "Dell Rusk", the secretary of US defense.
  • Bandolero
    • Don Rodrigo crosses this at the very beginning of the series, ordering to burn Bandolero's house and killing his father in the fire. He just gets worse by the end of the series, betraying the Governor, abusing Maria, killing Don Candido, Bandolero's Parental Substitute after he tries to defend her and abusing his authority shooting his general Jeremias in the arm after he refuses to kill Bandolero.
  • Batman: The Animated Series:
    • The Joker's serial murder spree (complete with victim photos) using laughing gas in one of the earlier episodes.
    • Roland Daggett crosses this when he tries to blow up Crime Alley, knowing fully well that there are people that live there. It was also shown some of the residents are children. Daggett's actions would have resulted in several people dying and he would have no problem or remorse to indirectly murder them for his own gain.
    • Daggett's most famous victim, Matt Hagen aka Clayface, crosses it in "Growing Pains" when he reabsorbs his own "daughter" Annie, a broken-off piece of himself that had gained sentience and her own set of morals, back into himself then laughing it off. Seriously, it's at that moment Hagen stops being a Tragic Villain and becomes as monstrous as Daggett himself.
    • The episode "Showdown" is about Arkady Duvall who has already crossed it according to Jonah Hex who has tracked him across twelve states "on account of what he had done to a girl back east" and as if that wasn't enough a barmaid at the beginning of the story tells Hex "He hurt one of my girls real bad." They don't go into detail, but he at the very least violently assaulted them. When the man appears in person, he's whipping one of Ra's workman for slacking, when all the guy was doing was trying to pick up something he'd dropped. When Hex is caught spying on them, Duvall orders the workers to lower him head first into a vat of molten lead, sealing him as a murderer along with abuser.
    • The Sewer King crosses the line by kidnaping children to use as slave labor and steal things from him. He trained them to be severely photophobic and afraid of adults. He also scares them with his trained crocodiles and makes it forbidden for the children to make a sound, punishing them by shoving them into a tiny little room with bright lights without food or water for hours - and sometimes, he does it on a whim, even to a kid who managed not to utter a peep despite the extreme scare tactics. In the Animated Series, the Sewer King was one of the few villains Batman had seriously considered killing on the spot, and that's saying quite a lot.
    • Ferris Boyle starts crossing this line when he interrupts Victor Fries's cryogenic experiment that can save Nora's life, even though Victor warns it could kill her. But when does he permanently cross it? By kicking Victor into a collection of chemicals that started his transformation into Mr. Freeze and leaving him and his wife to die. Even Batman is horrified at what the newly named Humanitarian of the Year did and leaves him encased in the iceberg instead of breaking him out with the coldly delivered line "Good night...Humanitarian."
  • Batman Beyond: Return of the Joker gives the Clown Prince of Crime a rather infamous line-crossing moment: he kidnapped Robin, tortured and mind raped him for three weeks, mutilated him, "fixed" him up as Joker Jr., and invited Batman over to see his work in detail (which included home video of the boy's torture labeled as "Our Family Memories"). He then reveals that he's learned Batman's secret identity, mocks him for it (and for not having the balls to kill him after all this), and knifes him before he tosses "J.J." a spear gun to finish him off with. Also worth mentioning that this particular MEH crossing was the former page picture.
  • 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.
    • Ghostfreak wanted to plunge Earth into darkness, the result of which is shown to be horrifying mutations of all living things. That was just a side effect of his plan that he didn't even care about.
    • Kevin 11,000, the future version of Kevin as an adult, crosses the line when he decides the best way to take revenge on Ben is to kill Ben's 10-year old son. And when Kevin's own son tries to stop him, he literally throws him aside and shows that he doesn't care about him at all, and then seems perfectly fine trying to kill him too when he fights back.
    • Zombozo gets his by kidnapping a 10 year old girl and draining her of her energy until she's nothing but a shrivaled husk of her former self, speaking of it so lightly that it's implied it's not the first time.
    • 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 tight rope and then lighting it on fire underneath her, intent on either 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 good thing about this guy 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 irredeemability, 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.
    • 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 Omniverse, Malware crosses the Event Horizon when he destroys his own homeworld, Galvan B, in the finale.
    • Years after he crossed it in the original series, Vilgax undergoes Character Rerailment in Omniverse in And Then There Were None, where he unleashes a bomb that erases all timelines save for the one he's in now, where its version of Ben Tennyson doesn't have an Omnitrix. Essentially, he's wiped out entire worlds, wiped out a number of lives too great to count, including his own allies, even erasing the main timeline's Ben Tennyson from existence, all to exist in a world where he can easily overcome a Ben Tennyson who can't fight back and rule unopposed.
  • While most of the antagonists in The Boondocks are just irresponsible, greedy, or selfish Jerkasses, there are moments where some had crossed the line
    • Lamilton Taeshawn is not exactly a child you want to babysit, but he crosses the line when he outright threatens to shoot Riley simply because he doesn't want to hang out with him.
      • Others thought he crossed it when he killed a dog that was chained up and couldn't reach him.
    • Ed Wuncler Sr. pretty much kicks dogs left and right, but his most heinous crimes include:
      • Tricking Jasmine into slave labor in her own lemonade stand with false promises of a pony so that when people start protesting, he can make a killing off "cruelty-free lemonade" and stick Jasmine with a $300 bill, as all the money she made was not enough to cover the expenses of professionalizing the stand at Wuncler's request. Wuncler even goes so far as to blame Jasmine for the failure of the stand!
      • Giving Granddad his own soul food restaurant, knowing the food is so unhealthy and addictive, the resulting crime rates would devalue neighboring Meadowlark Park enough for him to purchase and develop it cheap.
      • Having his grandson and his best friend set bombs in a building just to kill ONE man so that can play him up as a national hero and sell loads of merchandise.
      • Most damning of all is that all his evil acts are for the sole purpose of money, despite being rich enough to have connections to the president.
    • Wuncler's son is as bad as his father; when Robert was in his debt, he has Robert sell himself and his family into slavery and has them live and work in a realistic slave themed theme park, along with the others in his debt.
      • Uncle Ruckus crosses the point of no return by taking part in running said realistic slave themed theme park, whipping Robert (the closest thing to a friend he has ever had) and taking sadistic delight in their torment. He shows extreme glee when Huey is about to have his foot chopped off.
  • The Batman: Joker's torture of thugs is certainly crossing this, plus what he did to Ethan. And Tony Zucco crosses it in the first ten minutes of his appearance by killing Dick Grayson's parents (before he became Robin) just because Mr. Grayson called the cops when Zucco got a bit threatening.
  • Captain Planet and the Planeteers:
    • Verminous Skumm crosses the line in almost every episode he appears, but the most infamous moments are in episodes "Mind Pollution" and "A Formula For Hate": in the former, Skumm hands out a mind-affecting drug called "Bliss" to teenagers, deliberately causing them to go insane just for the joy of ruining their lives and those of their friends and families. He even temporarily has Linka, one of the Planeteers, turned into a drug-addicted lunatic by her own cousin Boris, who had also become a drug-addicted lunatic and eventually dies from a fatal overdose of the drug, thus making Skumm indirectly responsible for Boris' death. And in the latter, he harassed an HIV positive teenager by spreading lies about HIV/AIDS because the kid was an easy target for him to use along with the naivety of the townspeople about HIV/AIDS to spread hatred and take over the world. Almost every episode featuring Skumm has him crossing the MEH, but these two episodes are his most infamous Moral Event Horizon moments.
    • Dr. Blight crosses 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 (sure he was Captain Ersatz and was only referred as "The Fuhrer", but it was obvious who he was supposed to be). The Planeteers even say that this is low, even for Blight.
    • Zarm is one nasty work himself for two words: scorched earth.
  • In 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.
    • Another candidate for this trope comes in "A Rodent Like This", Cleveland gets heavily attached to a rat and raises it as a pet. The rat winds up biting Donna and when it's confirmed the rat has rabies, Cleveland decides (at first) to not have the rat killed to test it for rabies, which basically meant he would rather let his wife die than to kill his beloved "pet". Luckily, Donna strong-arms Cleveland into agreeing with her and the doctor.
  • Codename: Kids Next Door:
    • Grandfather was also the one who's responsible of making Father who he is. He somehow traumatized his own son into being scared of broccoli.
    • While most of the villains are willing to hurt or even outright kill children, Nurse Claiborne tries to kill Numbuhs Three and Five in cold blood! She is notable for being one of the few villains actually referred to In-Universe as insane, in a show where all the villains would be regarded as sociopaths in a Real Life setting.
    • Chester trying to feed kids to sharks. Specifically, sharks that can drive cars.
    • Father himself crossed it when he brainwashed Sector Z into The Delightful Children from Down the Lane.
  • Though he isn't nearly as bad as the Devil in The Bible, The Red Guy crosses this in Part-Time Job, an episode in which Chicken was looking for employment and worked for him. The only catch was him being stripped of his feathers and almost being cooked alive in one of The Red Guy's schemes.
  • Danny Phantom played it oddly straight with Danny's alternate future. The whole "Dark Danny creation" scene was horrific and it horrified even Vlad, which really says something. Also see Dark Danny's first appearance where he apparently kills multiple people on screen. Ax-Crazy, indeed.
  • While the villains of Darkwing Duck are often Laughably Evil, Negaduck crossed this in "Just Us Justice Ducks." When the heroes surrounded him, Negaduck threatens to throw a switch that would kill everyone, including himself. And even after the heroes back down, Negaduck decides to do it anyway out of pure spite.
  • Flintheart Glomgold and the Beagle Boys in DuckTales (1987) were Obviously Evil from the start with their card carrying and cartoon-ish villainy. But they've finally crossed it in the Grand Finale when they've turned Huey, Dewey, and Louie into golden statues. Luckily, it soon bites them in the ass when they suffer the same fate.
  • Near the end of the Ed, Edd n Eddy series, Eddy's Brother crossed this within seconds of making his first appearance when he began to mercilessly beat the shit out of Eddy, and freely admits he's always done this to him.
  • The Fairly Oddparents movie "Wishology" has the Lead Eliminator trying to kill Timmy is bad enough. But when he became the Destructinator, he plans to destroy the world in a Earth-Shattering Kaboom.
    • The Pixies crossed this in "School's Out: The Musical" with the revealed they'd kidnapped a child and raised him for his entire life as their own personal Tyke-Bomb to try and take over Fairy World and the Earth.
    • The Anti-Fairies crossed this (and if "School's Out" wasn't their's, this certainly is for the Pixies) by using Poof as a weapon to destroy Fairy World for revenge, then choosing to destroy the Earth For the Evulz.
    • The whole gambit Norm pulled in "Fairy Idol". He was already a Jerkass Genie, but the way he ruins Timmy's and Chester's lives is just terrible.
    • Remy Buxaplenty was originally a Villainy-Free Villain who was merely jealous of Timmy's Fairies and happiness, and while he might do an underhanded tactic here and there, like when he tricked Timmy by faking friendship so his life would be too perfect and his fairies would leave him, he never resorted to violence. He went from sympathetic Lonely Rich Kid to full-on Card-Carrying Villain as of "Operation F.U.N." where he, Juandisimo and Chief Shallow Grave put Timmy and his friends through Training from Hell, running them absolutely ragged and cutting Timmy off from his fairies by having them confiscated in goldfish form. The MOH crossing really comes in when he traps them under a butterfly net, which renders them powerless with a missile ready to obliterate them. He was willing to KILL Cosmo and Wanda!
  • In the Forest Friends episode "Bush School", Anthony's father Mark crosses this when he tries to start a forest fire.
  • In Berry's second and last appearance in Foster's Home for Imaginary Friends, she ties up a family and tries to KILL Mac.
  • 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, then sleeps with Amy. So, yeah, the jerk used a widow's husband's death.... to get laid.
    • If he didn't cross it then, Zapp definitely crossed it in "In-A-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. Through the episode, Zapp appears to be helping Leela get better. Then we find out that the planet they crashed on is Earth, and Zapp has not only been using their current predicament for an Adam and Eve Plot-style seduction, but placed the hazards there 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: they originally planned for Zapp to get off scott-free, but changed it to Leela punishing him in a rather fitting manner.
    • His first appearance in the series, Love's Labors Lost in Space, had him describe his "heroic" victory against a rampaging army of Kill-bots: He knew each Kill-bot had a preset kill-limit, so he just sent wave after wave of his own soldiers to die at their hands until every one of the robots had reached its limit and shut down.
    • Bender crosses it in " A Pharaoh To Remember" when he makes the decision to become the next pharaoh of Osiris 4 after its previous pharaoh dies in an accident. He then proceeds to make all the slaves of Osiris 4 take on the grueling task of building him an oversized statue with a flamethrower in a mouth that constantly screams "remember me" as Bender desired to be a remembered figure. His actions in that episode even had him treat Fry and Leela like slaves.
    • Richard Nixon's Head crosses it in "Crimes Of The Hot" when he attempts to commit genocide on all the robots of Earth by tricking them into attending a party on the Galapagos Islands so he could exterminate them all there. His reason for doing this was to provide a quick solution to the global warming problem but his actions are considered to be an act of genocide and racism and it can be considered a hate crime.
    • Ogden Wernstrom also crosses it in the same episode for helping Nixon attempt the genocide on the robots.
    • Most of the citizens of Earth cross it in " A Taste Of Freedom" when they decide to form a mob against Zoidberg and call for his death just because he ate a flag out of patriotism and euphoria for Earth, which forced Zoidberg to seek asylum in the decapodian embassy to avoid getting lynched. Nixon and even Earth's supreme Court joined in on this.
    • Yivo crosses it when in "The Beast With a Billion Backs", shklee decide to mate with everyone in universe gamma and make all of them "love the tentacle", which is to say that Yivo forced Shkler tentacles into everyone's necks and did that to everyone except Leela. Given the context of the situation, Yivo technically raped almost everyone in the universe. All of the people who got tentacles got very angry when they found out but their anger against Yivo quickly disappeared.
  • G.I. Joe: Renegades has several of its main baddies crossing this:
    • Cobra Commander's exact crossing is hard to pin down, but his general complete disregard for any innocent life lost in the process of any of his schemes makes him a pretty unambiguous monster.
    • Cobra as a whole crosses this in "The Anaconda Strain" where its revealed that they plan to release a disease they have made into populations and then charge high prices for the cure that Cobra also made.
    • Baroness crosses this in "Going Underground". When the Mook operating Cobra's underground tunneler protests that if they keep going at the speed the drill is going at, they will cause untold damage via seismic activity, what is Baroness' response? To electrocute him and then "thank" him for his "misplaced concern", wearing a Psychotic Smirk the whole time. Then she takes up control of the drill herself.
    • Mindbender crosses this in the episode "The Anomaly" when, after Tunnel Rat points out that, if the Bio-Vipers he rigged to self-destruct do blow up, the explosion they cause from igniting all of the flammable materials in the sewer will blow up all of Brooklyn. This is Mindbender's response:
  • Gravity Falls:
    • Gideon started out as a stalker who manipulated Mabel into being in a relationship with him, even though she likes him more as a little sister. Then he tries to cut Dipper in half with lamb shears when he tries to interfere on Mabel's behalf. In-universe, Mabel decides she wants nothing to do with Gideon after that.
    • The entire reason for the Lumberjack Ghost terrorizing the Northwest manor is because of Nathaniel's own MEH. Basically he demanded that the lumberjacks built a prestigious manor for him and in return, he "promised" to give them a grand party in return. This process cost the lives of many woodcutters and took a considerable effort to complete. And what does Nathaniel do once the building is complete? He goes back on his promise and betrays them once its over, turning away many upset builders and indirectly causing the death of a Corduroy worker who in his dying words, vows to make the Northwest family pay for what Nathaniel had done.
    • Preston Northwest was willing to let all his guests (including children and old handicaps) die at the hands of the vengeful Lumberjack Ghost that Nathaniel's selfishness had brought upon his family just to uphold his own refined image. Not to mention mentally abusing Pacifica into becoming the Alpha Bitch that she was throughout Season 1 and a good part of Season 2 through Pavlov conditioning.
    • Filbrick, even though was only shown in a flashback, is shown to be an even worse abusive dad than Preston when he kicks out Stanley not because he ruined his brother Stanford's college dream but because he cost his family the potential to get rich from Stanford's genius. As much of a Rich Bastard as Preston is shown, at least he somewhat cares about his daughter or at the very least, never disowns her for simply defying his orders.
    • When he first appeared in Season 1, Bill Cipher was interpreted as a Punch-Clock Villain who enjoys his job a bit too much. But Season 2 arrives and we see Bill for the monster he truly is. In his reappearance, he tricked Dipper into a deal to possess him and then proceeds to torture his body to the point of being hospitalized and nearly tricks Mabel into either handing over the journal to be burnt or fall down and ruined her puppet play. As if that weren't enough, he threatened to murder the same children unless Ford gives him the code to breaking the barrier keeping him and his creatures in Gravity Falls.
  • In season 3 of Jem, Eric Raymond crossed it when he destroyed the master tapes to the music of Jacqui Benton, Jerrica's mother.note  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...
    • The Misfits crossed it in "The Fan", where they cause poor Jerrica to have a *serious* mental breakdown.
    • The Stingers cross this in "That Old Houdini Magic", either when they try to con an old woman out of her money, or in the next episode when they essentially psychologically torture a girl purely for free clothes.
  • Justice League:
    • Some - if not all - of the many things that the Justice Lords (Knight Templar counterparts of the League) did in "A Better World". Lord Green Lantern attempts to kill JL Green Lantern immediately rather than disarm him or knock him out.. Also, when Lord Wonder Woman knocks League Batman down, she picks up a chunk of building rubble to finish him off. From the DVD commentary, the writers did that on purpose so that it showed that the Justice Lords while having good intentions, they ultimately are truly heroes turned 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, 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, referring to moral lines he never thought he'd cross, coolly told him that "one more won't hurt", making it clear that to this Superman, the death of a Flash from another reality 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. The true Start of Darkness is probably when Superman kills Lex Luthor, who was elected president and was responsible for Flash's death. However, it is ambiguous since Luthor was about to hit the Big Red Button, probably to start a nuclear war. Afterwards, even Batman says that Supes made the right decision.
    • Minor villain John Dee / Doctor Destiny in the episode "Only A Dream", where he "operated" on his wife in her dreams, torturing her until she died of fright, shortly after he had found out that she was planning to leave him for another man.
    • Orm, the estranged brother of Aquaman, tried to kill his brother's infant son Arthur Jr. Arthur Sr. did not take it well... At all. Primarily because aside from trying to have his own brother killed and taking control of his throne, Orm planned to lead a war against the surface-dwellers, using his own nephew as bargaining chip to ensure his sister-in-law Mera's cooperation, and not only did Orm try to ensure that Mera would never see her son again regardless... He put both his brother and said brother's infant son in a Death Trap. And the only hope Papa Wolf!Aquaman had of saving both their lives was to essentially mutilate himself! Only having time to break his right hand free before he and Arthur Jr. began to slowly plummet towards the lava of the volcano they were shackled to, Aquaman was forced to use his metal belt buckle to sever his left hand, which is later replaced with a prosthetic harpoon.
    • Project Cadmus practically made a habit of doing this, even as they claimed they only had the good of the world at heart. Abducting metahuman children and youths to rear them as super soldiers, genetically engineering metahuman super soldiers and not only not caring that the process is unstable and so the clones inevitably die after a few weeks, but seeing that as an actual bonus, creating Doomsday, cloning Supergirl and then using the clone as a Super Soldier and assassin to keep their agenda secret, attempting to nuke an island with a kryptonite-based atomic missile in the hopes of killing off Superman and Doomsday in one shot, sending a team of supervillains to steal a magical superweapon from the Justice League's headquarters, working with freaking Lex Luthor to discredit and aggravate Superman... Yeah, Villain Has a Point that the Justice League could potentially take over the world... but, on the other hand, Cadmus does a hell of a lot more actual damage to the world than the Justice League ever does.
  • Mr. Cat from Kaeloo crossed this in the episode "Let's Play Gangster Poker", where he threatened to shoot Kaeloo and Quack Quack, who are supposed to be his best friends, unless they gave him money that he tricked them into thinking they owed him (in other words, which they didn't even owe him).
  • Kim Possible
    • Monkey Fist crossed it 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.
    • Warmonga and Warhok in the Grand Finale were about to kill Kim and stuff her as a trophy back to their home.
  • Floyd and Jolene, the villainous gators on Kissyfur, usually resort to trickery and being sneaky in order to catch Kissyfur and his friends for dinner. However, they cross the line BIG time in "The Birds and the Bears" when they steal Gus's paddlecab, which Kissyfur and three of his friends took a ride on with Miss Emmy Lou's niece Donna to prove that they were "cool", and trick Gus into following them so they can lure him into quicksand to drown and die while they use the paddlecab to catch Donna and some of the other critters for dinner. As expected, they get their just desserts after Kissyfur, Beehonie, Toot, and Miss Emmy Lou free Gus from the quicksand and soon free the captured critters and retrieve the stolen paddlecab.
  • Kung Fu Panda: Legends of Awesomeness, despite being Lighter and Softer than in film, has several villains that went too far.
    • Temutai, the king of the Quidahn, enslaves children and they always die in a few years. The only thing redeeming about him is the fact that he's a man of his word.
    • Hundun crosses this by threatening to kill Po's father just to force him to fight him. This also makes things personal for Po.
    • Tong Fo counts too, wanting to destroy the Valley of Peace for no apparent reason.
    • Ke-Pa crosses it when he temporarily killed Po.
  • Disney's The Legend of Tarzan has Professor Philander, rival and Evil Counterpart to Professor Porter has the same goofiness and is generally a Harmless Villain most of the time, until he went from silly to downright irredeemable when he cuts a rope where Tarzan's hanging on, sending him to fall to his apparent death. To make matters worse, rather then letting his rival check on his son-in-law, he then plans to strand him into the sea and throw Tarzan overboard just to spite his rival.
    • Lt. Colonel Staquait crossed it by ordering Hugo and Hooft to burn a village full of mostly innocent women and children.
  • Daffy Duck crosses the MEH in the 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 yacht and attacks him for it.
  • Metalocalypse,
    • Dr. Rockso, one of the most popular characters on the show, 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.
    • Mr. Salacia crosses in the two-part season 4 finale, in which he brutally murders Roy Cornickelson, the elderly head of Dethklok's record label and one of the few completely good characters in the show.
  • 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. The shooting is effectively the point where Clay stops abusing Orel through mere neglect and misdirection and becomes actively, maliciously obsessed with destroying the boy's innocence, just so he can prove to himself that his own misery is natural and not because Clay himself is horribly twisted inside.
  • My Gym Partner's a Monkey
    • Nurse Gazelle crosses this in "The Hyena And The Mighty" when she chases Rufus Hyena trying to shave his fur off. Doesn't seem too evil? Well, Rufus was in a state of shock and depression and was busy crying his eyes out because Adam insulted him. The nurse doesn't care about Rufus' feelings or emotional well being; she outright TERRORIZES him while he's in a sad mood by chasing him with clippers just so she can make herself laugh. Also, keep in mind that Rufus is only a kid and would most likely get emotional scars from the incident. Sure, no blood was shed but the psychological trauma poor Rufus Hyena has to endure is just sickening and gut-wrenching. From the same episode Adam Lyon pretty much jumps off the slippery slope when he not only insults Rufus Hyena and doesn't care about him when Windsor explains he may be dying but near the end of the episode, Adam threatens Rufus with physical violence if he doesn't stop crying, despite Adam being the one who made the poor hyena cry in the first place. It is by far one of the most evil things Adam has done. It's a good thing karma catches up to him in the end. (Gazelle, however, gets away scot-free, but it could be argued that Adam deserved it more for starting the whole serade in the 1st place.)
    • Jake Spidermonkey crosses it in "Poop Scoop" where he tries to save the school paper by repeatedly slandering his supposed best friend Adam with false rumors of romantic involvement with various female faculty members. What's worse is despite getting what he wanted (He only uses the newspaper as TP), he continues to slander Adam For the Lulz!
  • The Powerpuff Girls:
    • Dick Hardly crossed the MEH when he kills a Buttercup clone for its Chemical X. He crossed it even further when he attempts to murder the real Girls for their own Chemical X and forcing the Professor to watch.
    • Him crossed the line in "Speed Demon" during a Bad Future where he took over Townsville, turned it into a post-apocalyptic place, and made the Townsville citizens all depressed and zombielike.
    • Mitch Mitchelson torturing and flushing Twiggy the hamster down the toilet in "Getting' Twiggy With It".
  • Phineas and Ferb:
    • The alternate Doofenshmirtz in the Movie did this as well. It was bad enough he transformed the alternate Perry into his cyborg general and took over his Tri-State Area, which left the alternate Phineas and Ferb to live a reclusive life without summer for 5 years. He even tried to feed the original Perry and the Flynn-Fletcher kids, as well as the original Doof, to a monster called a Goozim while initiating his invasion on the original Tri-State Area.
      • The alternate Doof's wife (known as the alternate Charlene) in the episode sequel did this as well, as she transformed 25 animal agents into cyborgs to serve for her family during their reign. She even planned to turn the alternate Flynn-Fletcher kids into cyborgs after tricking them into freeing her husband from prison so that they can take down the entire Resistance.
    • The Drill Sergeant Nasty in "Phineas And Ferb Get Busted" who broke both Phineas and Ferb's spirits simply because they're being creative by the way he lied to their parents and the way he treated the boys. He would've been a monster..... if he existed that is.
    • However, none of these are compared to Aloyse von Roddenstein (or Rodney for short) in Phineas And Ferb Save Summer, as he formulated an infamous plot to send the Earth into a Ice Age based on one of Doof's successful schemes, something that even Doof is horrified to learn about. After getting his fellow members of L.O.V.E.U.F.F.I.N. to capture nearly all of O.W.C.A.'s agents and sending the world to perpetual winter, Rodney became more than willing to finalize his plan for world domination that would endanger billions of lives. He even went too far by disabling the reverse switch and self-destruct button on his machine to ensure his plan would succeed, which only provokes a furious Doof to defeat him for good; even Perry personally helps Doof in foiling Rodney's plot, knowing that the cataclysm would put the entire Flynn-Fletcher family in danger as well.
  • Bluto from the Popeye cartoons crosses the line in almost every episode whenever he harms Olive Oyl after she rejects him, which includes kicking Olive off a runaway roller coaster in Abusement Park and trapping Olive in a straight jacket and then approach her menacingly in The Royal Four Flusher.
  • The Raccoons: Milton Midas ultimately crosses the line in "The One That Got Away" by having the pigs dump toxic waste into a beloved fishing hole which is a favorite among some of the Evergreen Forest's residents. And in the end, the lake became irreversibly dirty. Even the usual Big Bad Cyril Sneer is disgusted by what Milton did:
  • At the end of the second season of ReBoot, Megabyte and Hexidecimal team up with Bob to stop the Web Creature invasion. However, near the end of the episode Megabyte launches Bob into the Web and takes over Mainframe.
  • Recess: In the episode "The Biggest Trouble Ever" the Recess Gang accidentally breaks the statue of Thaddeus T. Third III, the namesake of Third Street school, thus becoming hated by the entire town. They are labeled "The Destructive Six" and are given menial jobs by Principal Prickly and Ms. Finster as punishment. It goes too far when Mayor Fitzhugh and the City Council decide to send the gang to six separate schools, despite the fact that they broke the statue by accident and were genuinely remorseful. This shocks everybody (even a shocked Prickly and Finster think that this punishment is way too extreme). Luckily, Thaddeus T. Third V (grandson of Thaddeus T. Third III) called the Mayor out on this and revealed that Fitzhugh intentionally tried to break the statue when he was a child. Most of antagonists in this series are jerks, but Fitzhugh's hypocrisy is notable.
    • Benedict's plan, if you apply Fridge Logic to it, involved moving the sun away to have "no more summer"; would've killed all life due to extreme freezing conditions.
    • Dr. Slicer was already cruel and heartless, but when he demanded the cannon to be made functional, he really showed his un-hidden dark side.
  • Regular Show:
    • Night Owl seems like your average Disc Jockey at the time, typical boorish and obnoxious behavior. However, he soared to irredeemable when he held the contest with a prize of a vintage muscle car for the last person standing on top of a huge billboard. When he discovered Mordecai, Rigby, Muscle Man, and High-Five Ghost are planning to share if they won, Night Owl not only turned them against each other, but while they were fighting, he froze them in liquid nitrogen for at least two millennium. After the gang thawed out, they found out that Night Owl had tricked them, had no intention of giving away the car, and had meant to keep the contest going forever so he'd become eternally famous! In a show where Eldritch Abominations are the norm, Night Owl makes it clear that even a normal human being can be quite monstrous if sufficiently consumed with Greed.
    • Klorgbane The Destroyer crossed when he destroyed Skips' high school prom (from way back when he was a mortal known as Walks), knocked out the principal, and got Walks' girlfriend, Mona killed in the crossfire just so he could fight the yeti.
  • Rick and Morty:
    • Rick himself crosses this at the end of the season three premiere when he (at great length) explains to Morty that all his of heroic actions throughout the episode were a calculated gambit to get Jerry and Beth divorced and allowing him to become the unchallenged family patriarch, and how Morty now has to go on all his adventures and can't do anything about it because Beth will hold him in higher regard for saving him and Summer. Assuming he's not lying about it though.
      • Rick may have crossed the MEH earlier in "Rick Potion #9", after he gives Morty a love potion that ends up causing everyone to turn into monsters. Instead of finding a cure for these people (after three failed attempts only made things worse), Rick simply takes Morty with him and abandons their dimension, moving into a replacement dimension where the problem was already solved... at the cost of said dimension's native Rick and Morty dying horribly. Rick and Morty end up seamlessly replacing their deceased counterparts who are both buried in the backyard, and Morty is left visibly traumatized by the transpired events.
    • Tammy Gueterman crosses it in "The Wedding Squanchers" when after marrying Birdperson, reveals that her relationship with him was actually a Honey Trap set up by her and the Galactic Federation in hopes of crushing Rick and his band of rebels who were fighting against the federation. Her MEH moment arrives when she murders Birdperson with a laser rifle after previously telling him to sit back down, which he refused simply because he didn't understand what Tammy was actually doing. Her actions in doing that furthermore endangered Rick's family and a bunch of innocent guests who attended the wedding. She even goes as far as to rebuild Birdperson into a cyborg in the beginning of Season 3 for her to use as a weapon.
    • King Flippy Nips crosses it when he has his own son, Scroopy Noopers, sent to Plutanamo Bay prison just because Scroopy Noopers protested against his father's actions of drilling plutonium for riches, which was hurting Pluto itself.
  • Scooby-Doo! Mystery Incorporated:
    • Mayor Jones asks the kids to come to the Cicada Festival, saying he has a plan to protect them. He actually wants photos of them being overwhelmed by swarms of bugs for tourism purposes. And he gets worse: How about kidnapping a baby from people he knew, forcing said people to leave town by threatening to hurt said baby, and feeding 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.
    • Multiple parents in episode 5, abandoning their "spookified" kids with the assurance that the government will air-drop in food. And it was entire blocks of parents.
    • Brad and Judy, Fred's real parents, willingly firing a missile at a helicopter that they know Fred is inside without any regard to his safety in "The Horrible Herd."
    • It's hard to determine with Professor Pericles, as he excels at committing horrific acts in almost all his appearances, especially toward the end of the show.
    • The Nibiru Entity gets one when, after it is freed proceeds to try and kill Scooby-Doo and take his body as his own and when Scooby manages to get free, the Entity settles for Pericles (who willingly volunteers, not knowing what it will cost him), The Entity then eats Brad and Judy (after they had pledged their servitude), then Mr. E., then the rest of the town, all for power (and you can tell it's enjoying it), and it claims it will go on to devour entire galaxies. Then again, it is the most evil Annunaki ever. As such, when Scooby strikes the final blow that destroys it forever, it is VERY satisfying to see it vainly struggle to escape its fate.
    • Of course, in the end of the series, almost none of these qualify as Moral Event Horizon crossings anymore... because '''NOW''' they never happened, thanks to the Entity's destruction erasing The Curse Of Crystal Cove from history.
  • The Secret Show saw Doctor Doctor cross the Moral Event Horizon one episode when she tricked Victor and Anita into flying towards the Sun and then attempted to leave them behind and let them burn to death.
  • SpongeBob SquarePants:
    • Mr. Krabs has always been a miserly cheapskate, but throughout the series he's became much worse and has done many cruel actions. He crosses the MEH in "One Coarse Meal" when he starts exploiting Plankton's fear of whales by dressing up as Pearl and threatening to eat him. He harasses Plankton so much that he becomes suicidal afterwards; after he finds out that Plankton is ready to commit suicide, he simply laughs at Plankton's misery.
    • Plankton brainwashing and enslaving Bikini Bottom in The Movie. In addition, he was willing to have SpongeBob and Patrick killed so they won't foil his plan, having hired a hitman to do the dirty work.
    Plankton: Evil Plan Z is way ahead of you, baby. I've already hired someone to take care of those two. He's a vicious, cold-blooded predator!
    • In the episode "Demolition Doofus", Mrs. Puff crosses it with her attempt to kill SpongeBob in a monster truck derby when she got tired of his antics, even stepping in herself when he managed to prove himself a natural at it. Not just injure him, but kill him outright!
  • Many villains in Star Wars: The Clone Wars have crossed this:
    • Cad Bane, as fairly popular as he is, still crosses the line when he tortures a guy to death, on-screen no less.
    • Zygeerian Keeper Arguss wants to make sure Obi-Wan does not try to attempt anything against him, by dropping some Togrutan prisoners down a bottomless gorge. And then later, when the Republic has arrived to liberate the surviving slaves, he sets the system to dump the slaves into the abyss, and then smashes the panel to prevent Obi-Wan from saving them.
    • Osi Sobek crosses this when he gleefully shoots a captured Clone Trooper in the face.
    • The Trandoshan Slavers, what with their capturing and hunting Jedi Padawans, as in, teenagers, for sport.
    • Pong Krell, when he cruelly tricks 501st Legion and 212th Attack Battalion Clone Troopers into killing each-other before Rex realizes that they're being duped. Worst of all, among the clones killed is Waxer.
    • Pre Vizsla crosses this when he callously murders an innocent teenage girl in front of her father and then orders his men to torch the whole village. Why did he do all of this you ask? Because that aforementioned father and his people had demanded that the Death Watch give them back those among them who they had taken as slaves
    • Darth Maul takes a running leap over this in the fourth season finale. While most would argue that Maul had already crossed it when he killed Qui-Gon, Qui-Gon is a Jedi, Maul is a Sith. Nothing personal there. What is personal, however, is murdering a bunch of innocent people, including children, just to lure Obi-Wan for the sole sake of revenge. He may have also crossed it by killing Duchess Satine in front of Obi-Wan just to utterly devastate him.
  • Super Noobs
    • Count Venamus crosses it seconds after his début appearance when he serves poisoned food infected with the virus to several virus warriors attending the new virus warriors convention and sits back to see them turn into rampaging monsters, which was eventually stopped by the Noobs. His status as an MEH crossers is set in stone when he tricks Memnock and Zenblock into opening his prison pod then tries to murder them by shoving them in the pod and then launching it into space before attempting to murder the noobs again and this happened after the main cast tried to get him to do a Heel–Face Turn.
  • 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 Plundaar star system which was inhabited by billions to create the metal needed to forge the Sword of Plundaar. 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 Transformers Prime, Megatron, is revealed to have crossed the line multiple times back on Cybertron. Aside from instigating the very war itself, he developed a cybonic plague and a bioweapon out of toxic Energon, both of which wiped out most of the Autobots (and lord knows how many innocent Cybertronians) gradually turning the entire planet into the graveyard it is today. However, he arguably crosses the definitive line in "One Shall Fall", when he shoots Bumblebee with Dark Energon, nearly killing Raf in the process. While Megatron was unaware of Raf's presence at the time, his reaction later on establishes he has no problem inflicting off-world casualties. For Optimus, this was the last straw, as he saw no alternative than to destroy Megatron once this happened.
    • Airachnid crossed it millennia ago when she tortured Arcee and murdered Tailgate. Beyond that, we learn she's spent who-knows-how-many years hunting species and committing genocide. For fun. Whether this started before or after Tailgate's murder is unclear.
    • Silas crosses it when he works with Airachnid to kidnap June Darby and then shows he's willing to let Airachnid kill her and Jack, dismissing them as collateral damage.
    • In "Evolution", upon discovering Predaking's transformation, Megatron and his command staff plan the eradication of the newborn Predacon clones, before said clones are given the chance to turn on the Decepticons. Starscream suggests they set it up so the Autobots would look entirely responsible and turn Predaking's anger towards them instead of his creators. Even Shockwave, the creator of the clones, is coldly in favor of the idea, though that's in-character for him: he will always take the most logical decision available, be damned to the moral questions.
  • Hard to imagine that a show with silly villains like T.U.F.F. Puppy would have someone crossing the line, rather it's not any of the regular villains but a former agent of T.U.F.F, Jack Rabbit. At one time, Jack Rabbit was known as the greatest T.U.F.F. agent of all time, so it shouldn't sound bad when he's revealed to have undergone a Face–Heel Turn and lied to Kitty Katswell (who was his partner before he retired as a T.U.F.F. agent) to lure her into a trap, drain her mind of all her T.U.F.F. secrets, and sell those secrets to the usual Big Bad Verminious Snaptrap. However, Jack said that he'd done this to agents in the past, and his reason for betraying Kitty and T.U.F.F.: Money! That's right, no Start of Darkness, no sad backstory, it was all due to his Greed.
  • The Venture Bros. Many of Dr. Venture's actions are examples of the sort that would normally qualify him for crossing it. He's the star of a Black Comedy, however, so it's more funny than repulsive thanks to much Refuge in Audacity.
    • Rusty, in the first episode, removes a dog's skin (his own dog no less) because a makeup company wanted to find a new way to test makeup on animals. To be fair, it was to prevent the dog from dying, but that's still pretty horrible.
    • It's pretty much telegraphed that Tim-Tom and Kevin killed 24.
    • Limb releases The Monarch's prison mates just so that he can hunt them down like animals.
    • Molotov Cocktease crosses this twice: first at the end of season three, where she puts a bounty out on Brock Samson's head and tricks him into thinking OSI was the one responsible. Manipulating Brock just to further her career was more impressive than it was unforgivable... but in Operation P.R.O.M., she went and not only chose someone else (Monstroso) over Brock after long acknowledging his affections for her, but was also willing to die with him. Then, just as a final "screw you" to Brock, she told him if she were to die, the Blackhearts were ordered to kill all of Brock's friends. They only survived because Dr. Venture used mutant Spanish Fly on them. Which turned them into mutant Spanish flies.
    • The senior Dr. Venture has done several things that may qualify. His actions once caused a group of orphaned children to wander below his home for over 20 years, which he conspicuously did nothing about. One wonders if this is probably worse that his son's machine that was powered by the heart of an orphan. Making the thing with the orphans even more disturbing, it was very common for Jonas to make a project that risked the life and limb of others, and then promptly forget about it, sometimes midway through, giving him ample material for his section on this page.
      • On a more intimate level: acting as Rusty's therapist so that he could belittle his own son and tell him how ungrateful he was for not enjoying a life of constant danger, kidnapping, and isolation from his peers. If you didn't already think he was worse than Rusty, this about clinches it.
      • Creating an AI with full access to a nuclear silo was a pretty idiotic move to begin with. Not to mention he trapped the miniscule Dr Entmann in her control room for decades as well.
      • And then there's the Morphic trilogy, (Season 7, episodes 1-3, if you're wondering) which reveals the depths of his abuse of the Blue Morpho, a man he (allegedly) considered a friend. Said abuse may very well rival if not outright beat his abuse of his own son. Where to begin?!
      • Led his friend into various orgies, then used a sex tape of said orgies to blackmail him into becoming Jonas' pet psychopath, doing unspeakable things. Said unspeakable things ranged from seducing Dr. Z to murdering an arch.
      • Also, he had sex with the Blue Morpho's wife.
      • Upon the Blue Morpho's "death," he built him into the borderline-lobotomized cyborg Venturion, an act that disgusted his normally sociopathic friends then - after Venturion had a psychotic break, literally throwing what was once his friend in the trash.
      • Then, after Venturion/Vendata/The Blue Morpho reappeared, Jonas Sr. attempted to steal his body. All the while acting like he'd done the Blue Morpho a favor or acting like he was the ungrateful one.
    • Dr. Impossible using his ex-brother-in-law, a failed experiment who is constantly on fire (and screaming in pain) when awake as a green energy source to power his skyscraper. It says something about him when he thinks being green makes it morally acceptable. The Phantom Limb says it's basically the most deliciously evil thing he's ever seen.
    • Monarch's committed several deeds that may qualify as candidates for his crossing. Most notably, his forcing a prostitute to run a dangerous gauntlet inside the cocoon after they have sex was supposed to be one, but the sequence's Red Dragon homage and Monarch revealing that he stole the polar bear from Lost to serve as a guard-bear, made fans laugh at it instead.
    • In the season six premire, the Sovereign masterminds a plot to destroy the Gargantua 2 space station/casino hotel, to kill hundreds of the civilians on board so he can escape having to pay for his Deal with the Investors.
  • In Season 4 of Winx Club, Ogron, the leader of the Wizards of the Black Circle, 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. Aisha'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 way. This single act caused the distraught Aisha to join the Fairies of Revenge and separate herself from the Winx Club, and marked the point where the Wizards of the Black Circle sunk to a low no other Winx Club villain ever reached.
  • In W.I.T.C.H., you have a number of villains, but one who could easily stand out 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 murdered her. 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 WordGirl, the new villainess Miss Power crosses the line in her debut movie The Return of Miss Power. She severly curb-stomps the villains, and severly taunts them. She then teaches WordGirl to say mean words. She mocks the man who couldn't find the police station to the point where he cries, she manipulates the entire town into bullying each other, she gives WordGirl a No-Holds-Barred Beatdown when her plan for rule the Earth was discovered, and then gives her "The Reason You Suck" Speech. She even removes her star insignia. She throws Becky's mother into jail due to a disagreement that they had, and she tries to murder Dr. Two-Brains. Fortunately, WordGirl arrives just in time, and causes Miss Power to lose her power by not using mean words. She then has a Villainous Breakdown and leaves Earth.
  • X-Men: Evolution had one for most of the villains:
    • Magneto had it when he had his own daughter Wanda mindraped, just so she'd stay away from him. Said mindrape took place via replacing her memories of him abandoning her in a mental insitution, 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 no reason other than them being unable to fight Magneto. Later on she committed another heinous deed, kidnapping Scott, stealing his Power Limiter aka his ruby quartz glasses, and leaving him stranded in the middle of nowhere.
    • Duncan Matthews and his pals went from Jerk Jocks, to physically assaulting Scott unprovokedly after he was outted as a mutant, to post-graduation attempted mutant murder with mining machinery. That last one got them sentenced to life in prison. Duh.
    • There was also the soft-drink manufacturer who unknowingly laced his drink with mutant poison. You can tell he's genuinely surprised... then Mood Whiplash kicks in and he figures he can make a lot of money off the discovery.
    • Apocalypse was planning on using his machine to turn the populace into mutants... But even he notes that this may kill much of the human population, due to their bodies not being able to take it. He still was willing to go through it.
  • Wander over Yonder: Lord Dominator is seen as a hilarious, if highly destructive, villain. Then comes "The Bot". Bot 13, one of her competent robot minions, refuses to give her the location of a planet she wishes to destroy. She responds by smashing the poor bot, then tossing him into space, cementing her as a heartless monster.

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