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  • Jafar from Aladdin crosses this when he — after fooling Aladdin with his pedlar disguise and making him hand over the lamp from the Cave of Wonders in return for helping him up from the collapsing Cave Of Wonders — immediately reneges on their deal and tries to murder him with a dagger as soon as he has what he wants from the "street rat". Considering how he then tries to execute Aladdin later after he survives Jafar's first attempt on his life, it's all but outright stated that said murder methods he choses are with the intention of ensuring Aladdin will never be found after betraying and killing him.
    Aladdin: What are you doing?!
    Jafar: (raising the dagger) Giving you your reward! Your eternal reward.
  • In Atlantis: The Lost Empire, Commander Rourke, who planned to steal the crystal from Atlantis all along without telling Milo, punched the King of Atlantis, mortally wounding him given how old he is. It was enough for Dr. Sweet to turn against Rourke and try unsuccessfully to treat the King's wounds when everyone else was abandoning Milo and the people of Atlantis taking the crystallized Kida with them, even before Milo's sarcastic, fatalistic appraisal of the people he thought were his friends actually convinced Audrey, Vinny, Moliere, Cookie and Ms. Packard to join him and abandon Rourke, who had just crossed the line even further by punching Milo down for his "soapbox," and stepping on the picture of Milo and his grandfather, breaking the glass of the frame.
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  • Gaston from Beauty and the Beast comes close to this when he tries to blackmail Belle into marrying him by threatening to have her father tossed in the loony bin. He comes close to it still when, out of envy of the Beast, he breaks down and stirs the town into an angry mob to make them kill him. However, Gaston finally crosses this by literally stabbing Beast in the back after Beast spared his life (and wearing a very nasty smile while doing it). He falls to his death soon afterward.
  • Penny's agent from Bolt crosses it when encourages Penny's stressed mother to use her daughter's life-threatening burns for publicity. Penny's mom decking him at the end was totally deserved.
  • Lady Tremaine from Cinderella is established as a nasty piece of work throughout the film, and her deliberately breaking the glass slipper at the end is particularly cruel enough to be considered a possible candidate for her MEH since she did it purely out of petty hatred toward Cinderella (and she also shows no regard for the Grand Duke's life), but she truly seals the deal in the third installment, A Twist in Time, when she poofs Cinderella in a twisted pumpkin carriage with Lucifer as its human driver, and attempts to get Lucifer to kill Cinderella (especially heinous because previously, she had been satisfied with simply making her life a living hell). She also has Anastasia posing as Cinderella to fool the prince. If anyone doesn't know, this is rape by association. As The Nostalgia Critic put it:
    Nostalgia Critic: She had no magical powers, no minions, all she had was complete control over one person's life. And man, did she squeeze every last drop out of it.
  • In Frozen, if Prince Hans of the Southern Isles using Anna and lying to her the entire time isn't bad enough, then there's him leaving her to die followed by his attempted murder of Elsa. Though Word of God states that having 12 older brothers, he was given no love growing up, ultimately pushing him into that direction.
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    • It's later revealed in the Tie-In Novel A Frozen Heart that Prince Hans' father, the King of the Southern Isles, crossed it long ago by abusing his 13 sons for his own ego so they'll be transformed into his sycophantic henchmen, aside from tormenting his subjects for not providing enough money or insulting him behind his back. And because Anna and Elsa wanted Hans out of their lives as soon as possible, they have no idea just what kind of person they sent him back to, meaning the king continues to make Hans' life a living hell.
  • The Great Mouse Detective: Ratigan's exposition song mentions he drowned widows and orphans For the Evulz. And halfway through the song, the audience gets more directly acquainted with him when one of his drunken mooks calls him a rat (he is a "real big mouse", if you please!) and Ratigan has him eaten alive by his trained cat. And when Basil successfully undoes all of Ratigan's plans once and for all, he really loses it: turning feral and viciously beating Basil half to death on-screen.
  • Most Disney villains are goofy, somewhat quirky people, and even the darker and nastier types, such as Queen Grimhilde, Lady Tremaine, and Scar, had a funny and/or quirky moment or two. But not Judge Claude Frollo, from their version of The Hunchback of Notre Dame. If he didn't cross this after almost throwing a baby down a well just after indirectly killing his mother, he definitely did upon burning down multiple homes with families still inside them. The fact that Frollo uses religion to justify his atrocities only makes it worse. In the opening sequence, the music seems to indicate a crossing of the M.E.H. when he decides to kill baby Quasimodo. About five seconds after he says, "A baby...? A monster!", the music jumps keys and tempo as he moves towards the well, and is supposed to make you realize "Oh shit, he's going to kill a baby in the first five minutes of a Disney movie!". Right there and then, you know there will be no chance of redemption for this guy.
  • The Lion King:
    • The Lion King (1994): Scar evidently crosses this by murdering his brother Mufasa. It even seems, from Scar's facial expression at the edge of the cliff, that he realized there would be no going back once he did this, yet he did it anyway. Further evil actions (such as tricking Simba into blaming himself, or sending the hyenas after him) were done to get away with murdering Mufasa, which makes that the most likely candidate for Moral Event Horizon. When Simba finally tries to use the same words against Scar that he used against Simba (to "run away and never return"), instead of complying, proceeds to engage in an epic battle with Simba. But just before Simba and Scar battle, the latter foolishly blames the hyenas for everything, effectively sealing his fate when Simba leaves him to them.
    • In the sequel The Lion King II: Simba's Pride, Zira threatens to kill her own daughter for refusing to participate in an attack on the pride lands. Zira's own followers defected to Simba after this.
  • The Little Mermaid:
  • Planes: Ripslinger sending Ned and Zed to sabotage Dusty during the China-Mexico stretch.
  • Governor Ratcliffe from Pocahontas crossed this when he tried to shoot the Chief after his fellow colonials chose to make peace with the natives, resulting in John Smith taking the bullet and almost dying. The settlers arrest him and have him shipped back to England in disgrace. All the while, he tries to blame everyone and everything but himself for what had happened, angrily warning them that they are the treasonous ones for turning him in.
  • Dr. Facilier of The Princess and the Frog has an entire plan that puts him over the line — in exchange for wealth and status, he's willing to sacrifice the souls of everyone in New Orleans to his "friends on the other side".
  • The Rescuers: Medusa, who kidnaps a young girl named Penny to make her look in a flooded well for diamonds, crosses this when she refuses to let Penny up even when Penny's life is in danger. Oh, and did we mention that Medusa makes several direct attempts on Penny's life with a shotgun when she tries to escape? And she might have killed her hadn't one of the animals helping the girl jammed a lit firecracker into the barrel of the gun, destroying it and leaving Medusa no other choice but to just pursue the girl on foot. However, what would've happened if Medusa's one chance of getting the diamond dies with Penny? Would she really want to waste that if getting the Devil's Eye is all she cares about?
  • The Rescuers Down Under: McLeach, who kidnaps a young boy named Cody to try to get the location of some eagle out of him, crosses this towards the end when he ties Cody to a crane, lowers him into a crocodile-infested river, raises him back out again, and would dunk the boy in again until the power on his halftrack goes out. When this happens, he takes out a gun to shoot the rope, suggesting that he was originally intent on murdering Cody anyway and just wanted to torture the kid first.
  • Though for the most part he's as Laughably Evil as the average Disney villain, Prince John from Robin Hood crosses it when he plots to use Friar Tuck as bait to capture Robin Hood, knowing Robin Hood will save any friend of his who's in danger. Even Sir Hiss is shocked to hear that his boss plans to hang Friar Tuck. He further goes over when he tries to murder Maid Marian in the alternate, extended ending, which makes it all the more understandable when King Richard has his brother locked up and notes that were it not for their mother, he'd have him executed then and there.
  • Maleficent in Sleeping Beauty after she condemns Princess Aurora (as a baby no less) to her doom by pricking her finger on a spindle needle on her sixteenth birthday — and all because she wasn't invited to the party. Partially this and likely partially just for fun, with even the not being invited thing as a mere direction towards whom was she going to destroy. The movie leaves room for interpretation as far as her motives go.
  • Snow White and the Seven Dwarfs. After Snow White has grown up enough for the mirror to declare her more beautiful than the queen, the queen orders her hunter to kill her and bring back her heart as a trophy (she even already had a box custom-made for the occasion). When that doesn't work, it turns out she's studied murder spells as a backup plan. When she learns that the Sleeping Death spell she's put on a certain apple will only leave Snow asleep and can be cured, she isn't fazed but rather delighted — because she's sure that the dwarfs will bury Snow alive! Snow must have had her hands full as the new Queen — she probably had to sort out some pretty sadistic lawbooks.
  • Clayton from Tarzan crosses this when he shoots Kerchak, Tarzan's adoptive father, then, much like Gaston, tries to kill Tarzan after Tarzan spares him, resulting in a gruesome Karmic Death afterward.
  • Mother Gothel in Tangled officially crosses the line either
    • When she stabs Flynn Rider and very nearly kills him, so that Rapunzel's secret would die with him.
    • Or arguably even before already when she sets him up to be caught by the authorities knowing that he will be sentenced to death, which nearly happens, but he escapes that, only to be stabbed by Gothel as mentioned above.
  • In Treasure Planet, Scroop crosses the line when he throws Mr. Arrow into a black hole and pins the blame on Jim, which earns him Silver's ire. Karma strikes Scroop right in the face when he tries to knock Jim into the depths of space, only for Jim to do the same to him.
    • Silver came very close to crossing the line for apparently burning the Benbow Inn, and for leading the mutiny on the trip to Treasure Planet. Thankfully, his relationship with Jim helps him pull a Heel–Face Turn.
  • In Wreck-It Ralph, King Candy crosses the line late in the film, where after all his plans to stop Vanellope racing have failed, he resorts to trying to beat her to death with a car-part simply to stop her from crossing the finish line and resetting the game. Some people say that he crossed it by putting Turbo Time and Road Blasters out of commission, making homeless dozens of characters, because he couldn't stand not being the center of attention anymore. Not only that, it's no secret that he would have no issue with putting almost all of Grand Central Station out of commission as long as his massive ego is satisfied.
  • Zootopia: Bellwether crosses it when she shoots Nick with the Nighthowler serum in an attempt to make him kill Judy. It's driven home when she chooses to stand there and watch Judy be hunted and killed, even giving a Psychotic Smirk when Nick clamps down on her neck.

Live-Action Films

  • Christopher Robin:
    • Giles Winslow Jr. crosses it when it's revealed that he spent the weekend golfing instead of helping Christopher Robin work out the cost cutting at the company. It's here that it's revealed that the whole 'swimmer or sinker' spiel he gave to Christopher was nothing more than a manipulation tactic Winslow spun just to get someone else to do his work for him, all the while knowing full well that his own job security was almost assured because his father Winslow Sr. is the company founder. Quite mild compared to what you'd normally expect for this trope, but in the context of the franchise, that cemented Winslow's status as a villain. Fitting for someone whose name sounds similar to "woozle".
    • Christopher Robin himself believes he crossed it at some point during World War II, and even confesses as much to Pooh. Being forced to kill countless of your fellow humans can do that to you. More pointedly, he had lost a lot of innocence he will never truly be able to regain in full, and the movie is about him regaining what he'd lost.
  • The Jungle Book (2016) has Shere Khan confront Akela and the wolf pack about why Mowgli was not handed over to him. Akela says that Mowgli is going back to the man village, so there will be peace for the boy and the wolves. In response, Shere Khan...just goes ahead and kills him, all for Akela apparently denying him his prize. Whatever sympathy Shere Khan had for what humans did to him, it's cost him a lot of that.
  • From The Lizzie McGuire Movie Paolo Valisari crosses it by manipulating Lizzie into posing as his look alike ex-girlfriend Isabella, and lip sync as Isabella at the International Music Video Awards, to ruin Isabella's career.
  • The Lone Ranger: Butch Cavendish and Latham Cole starting a war, all for silver.
  • Constantine from Muppets Most Wanted crosses this when he steals Kermit's identity and sends him to the gulag. He takes it further when he proposes to Miss Piggy under his Kermit guise, then attempts to have her blown up with a time bomb disguised as a wedding ring after the ceremony. He totally deserved the beating he got from Piggy and Kermit slapping him in the face during the climax.
  • Pirates of the Caribbean:
    • Captain Barbossa of the first movie and his men have done such a deed so many times when one would suffice as a MEH and their last time is the only time that viewers witness it first-hand, specifically the brutal opening attack on Port Royal that leaves many civilians dead, injured or just terrified and this includes toddlers.
    • Cutler Beckett, the new villain of the next two films, was an outright bastard and crossed the MEH around the time that he had a ten-year-old boy hanged for piracy or even just associating with pirates.
    • Pirates of the Caribbean: On Stranger Tides: Blackbeard crossed this when he had Syrena tied up half in the water for a slow, painful death to extract a tear from her. Phillip, who before stated that everyone had some good in them, admits he was wrong and there is no chance of redemption for Blackbeard.
  • TRON: Legacy: Clu is a dog-kicking program who takes pleasure in viewing and participating in games to derezz citizens in Tron City. It's not a question of if CLU crosses the line, but when. Here are some milestones:
    • Stealing Tron's light jet and leaving Tron to die in the Sea of Simulation after Tron refuses to shoot down the Flynns and crashed his jet into Clu's.
    • Clu kicking Kevin Flynn to the ground after Flynn apologizes for giving a flawed and impossible task. Yes, Clu might've just been doing his job, but taking out all of that anger and confusion on his creator like that?! It's no wonder Sam lost himself in rage and ran up to punch Clu's face twice afterwards.
    • And even before all of that, the genocide of the ISOs. Since he viewed the ISOs as an imperfection (as well as threatening his ability to create a perfect system, which is exactly what he was made to do), he purposely reprograms an ISO into a virus to infect and derezz ISOs in Evolution. This was not just used as a distraction for Flynn while he takes over the Grid, it was also used as an excuse to turn the Basics against the ISO population.
    • Turning the Games lethal, when Flynn explicitly made the Games non-lethal, which just seemed to be a dick move to punish Programs that annoyed him (and/or piss off Tron).
    • And "rectification"...Taking and twisting sentient Programs into attack drones. And then, when you try factoring in how much work must have gone into Rinzler and the twisted delight he likely got out of it.
  • Who Framed Roger Rabbit: Judge Doom demonstrates the Dip by dipping the cute little shoe affectionately rubbing his boots. What makes this even scarier is that as the shoe goes into the Dip, smoke not unlike that which comes out of the smokestack of an incinerator starts coming out of the Dip as if Judge Doom was using the thing to burn that poor shoe alive.
    • And if that wasn't enough to make you hate him, his plan to annihilate Toon Town just to build a freeway, and then revealing himself to be the Toon that killed Eddie's brother probably will.

Pixar

Your choice, Woody. You can go to Japan together, or in pieces! If he fixed you once, he can fix you again!
Stinky Pete, Toy Story 2.

  • In A Bug's Life, Hopper probably crosses the line once he kills two of his own underlings to pass his message: it's not just about the food, it's about keeping the ants in line. And it all begun because a freak accident ruined the food originally set out for the grasshoppers, making Hopper think he needed to tell them "You Have Failed Me". And thousands, if not millions, of puppies continue to be kicked afterwards, as one of his goons reveals Hopper planned to squish the Queen after they finished the mass food theft just to teach the "lesson". When this is about to happen, and after suffering a No-Holds-Barred Beatdown at one grasshopper's hands, Flik confronts Hopper with a "The Reason You Suck" Speech ("Who's the weaker species? Ants don't serve grasshoppers! It's you who needs us!"), but this pushes Hopper even further past the line, especially when the ants decide to stand up to the grasshoppers. In the ensuing chaos, an enraged Hopper tries to kidnap Flik, but when his attempt is foiled, this pushes Hopper so far beyond the Horizon that there is no going back, especially when Hopper confronts Flik again.
    Hopper: [rough with pure hatred] YOU THINK THIS IS OVER?!?!? ALL YOUR LITTLE SCHEME DID WAS BUY THEM TIME!!
    Flik: No, please! Please, Hopper!
    Hopper: [grabbing Flik's throat] I'll get more grasshoppers and be back next season! But you won't!
  • Cars: Chick Hicks was already bad due to his dirty racing tactics, but at the end when he purposely runs The King off the road — causing his crippling crash — and has no remorse for it, he unsurprisingly loses all his fans.
    • Cars 2: Although the Omnidroid (who we'll discuss later) apparently killed a lot of supers before it met Mr. Incredible, Zundapp does the exact same thing on-screen, and even that is nothing compared to his conspiring with Sir Axlerod to hijack Allinol so that people go back to the lemon's oil fortune.
    • Cars 3: Jackson Storm tries to ram Cruz Ramirez into the wall in the ending, and Rusteze's new owner Sterling was planning get Lightning McQueen to retire from racing forever so he can take over as the sponsor for Rust-Eze.
  • Coco: If Ernesto de la Cruz didn't cross it when he murdered his best friend Hector to steal his songs for the sake of becoming famous the second the latter had decided to quit the music career and return with his family, he definitely did when he doubtlessly threw both Miguel and Hector in a hole, in order to keep his reputation and fame in the world of the living intact, despite him fully well knowing that Hector would die for good if he gets forgotten, and that Miguel (who at that moment he believed to be his long-lost grand-grandson) will not be able to return home.
    • And if you still thought there was anything good or redeeming about him then attempting to throw Miguel off a cliff to his death in order to prevent him from bringing Hector's photo, and the truth about his career to the living world, all of this while shamelessly claiming to be innocent will make you think otherwise.
  • In The Incredibles, Syndrome's Project Kronus. It's all about luring Supers to his island knowing they will face his Omnidroid(s) for the sole purpose of being terminated - which he does over a dozen times before he gets to Mr. Incredible - and then later firing missiles at a plane that he was well aware had children on board.
    • Mr. Huph smiling and saying "Well, let's hope we don't cover him!" when learning that a man is getting beaten and mugged outside his window, then threatening to fire Bob if he leaves to help. Eventually, he gets thrown across the office by Bob when he reaches his Rage Breaking Point.
    • Despite his brief appearance, Bomb Voyage crosses it when he attaches an explosive to Buddy's cape to force Mr. Incredible to save Buddy, showing that he has zero qualms about potentially killing a child. The emotionless look on his face when he does it makes it all the worse.
    • In Incredibles 2, Screenslaver alias Evelyn Deavor is able to mind control supers and force them to commit acts of villainy, the very thing they stand against. even going as far as to create a decoy Screenslaver by hypnotizing a pizza delivery guy to be the scapegoat. When Helen challenges Evelyn on framing an innocent person, she displays a complete Lack of Empathy toward her victim and even justifies it by saying the pizza was cold and the delivery guy was surly. What is especially notable is when they force Mr. Incredible and Elastigirl to attack their own children.
  • Randall Boggs from Monsters, Inc. plans to kidnap small children so he can use the Scream Extractor on them, a device that sucks the scream and oxygen out of them, running the very real risk of suffocating them to death. And unlike Waternoose, who crosses the Horizon himself due to this same set of circumstances, he can't claim to be a Well-Intentioned Extremist, because his reason for doing it is petty jealousy against Sulley — jealousy which, as it turns out, goes back to the prequel, where it's revealed that all this time, Randall had been beaten out as Scare Leader by a college dropout, making his jealousy all the Harsher in Hindsight.
  • Toy Story 2 has the Prospector closing and locking the air vent after Woody says he wants to leave. Earlier on, the "how long will it last" speech seems reasonable enough, but going as far as to threaten to chop Woody into pieces so he wouldn't ruin his plan for them to be put into the toy museum is clearly unjustified, and in turn makes much clearer whose perspective we're encouraged to listen to.
  • Toy Story 3: While Lotso was already a loathsome character he crosses the horizon when he refuses to help Andy's toys escape the incinerator after they went out of their way to save him moments earlier. He even taunts them with the remark "where's your kid now, sheriff?", complete with a mocking salute and evil smile.
  • Charles Muntz of Up ties a child to a chair and drops him out of a blimp. Said child gets rescued, but still...
  • AUTO from Wall E may very well be a Well-Intentioned Extremist, but giving WALL•E painful-looking electric shocks and then throwing him and EVE down the garbage disposal tube really helps to cement audience disdain for it.

Western Animation

  • 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.
  • Big Hero 6: The Series:
    • Fans felt that Obake crossed it when he tricked Hiro into thinking that his dead brother was alive. This is even treated as one in-universe by Go Go and Wasabi, thinking that Obake really crossed the line this time.
    • It gets much worse in the season finale, where he plans on recreating the Great Catastrophe to make an artificial star, despite knowing full well it will destroy San Fransokyo and kill millions of innocents.
    • Liv Amara's clone Diane crossed it in "City of Monsters" when she forcibly turned her 16-year-old intern Karmi who idolized her into a monster and kidnapped Hiro and Baymax to force them to cure the real Liv Amara. When they succeed, she tries to mutate Hiro and then force the monster Karmi to kill him since He Knows Too Much.
  • 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.
  • As for the reboot:
    • Glomgold crosses it in the first episode when he leaves Scrooge, Donald, Launchpad, the nephews, Webby and his henchmen to die in the sinking Atlantis (which he himself sank).
    • It's revealed in "Jaw$!" that Magica De Spell has her own niece Lena enslaved to do her bidding. To make it even worse, "The Other Bin of Scrooge McDuck" has her now able to literally possess her to get what she wants. And then in the finale we find out that Magica created Lena, which for all intents and purposes makes Lena her daughter, and get to watch Magica kill Lena practically as soon as she's done what Magica created her for. Twice, if you count the murder of the physical body and the spirit that showed up later separately.
    • Jim Starling/Negaduck ran past the horizon and seemingly isn't going to be looking back. He took the fact that he wasn't going to be cast as Darkwing Duck in the big budget remake... a little poorly. As in he tried to hijack the picture, assaulted numerous guards and attempted to straight-up murder his replacement, including with an electric gun and a chainsaw. Then, after seemingly dying in an explosion, he's revealed to have become Negaduck, a completely evil villain.
    • Lunaris crosses it when it's revealed that he's planning on killing Huey, Dewey, and Louie just to break Scrooge and make him easier to finish off, something he gloats to Donald about with a sickening grin on his face. And when Penumbra learns of this, he electrocutes her without remorse.
  • Gargoyles:
    • Xanatos went over it for Elisa in "Metamorphosis". It's unlikely she'll ever forgive him completely.
    • Lexington was never really able to get over being duped by the Pack, though he eventually forgives Fox, if only for the sake of baby Alexander.
    • Demona goes over it truly in "City of Stone", where she ends up breaking, and thus murdering, an untold number of humans turned to stone.
    • The Pack all get one, when they irreversibly change their bodies into stronger but more monstrous forms, with the exception of Anti-Villain Dingo, who goes for a suit of powered armor that of course does nothing to change his actual body. If you're not completely sold, they each get moments later on.
    • Hakon crossed it when he enacted the Wyvern Massacre while the gargoyles were still stone- the equivalent of killing an unarmed person in their sleep. And later after death, when his ghost pulled Mind Rape on Goliath via transforming into the gargoyle's fallen brethren in order to torment him.
    • By extension, the Captain of the Guard crossed it by betraying his castle to Hakon and reluctantly allowing Hakon to commit the massacre. Unlike most of the examples above, he decided to make amends by stopping Hakon from reviving himself via Goliath's life energy.
    • Thailog crosses it when he attempts to betray and kill Demona while pretending to love her at the very latest.
    • Jon Canmore crosses it when he tries to kill Vinnie for disobeying him.
  • 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.
  • 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.
  • Motorcity :
    • Abraham Kane crossed it when he chose to mount attacks on Motorcity when he could have just left it alone.
    • Kaia crossed it when she tried to destroy Detroit Deluxe with chemical weapons.
    • Red crossed it when he decided to work for Kane.
  • 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.
  • The Proud Family:
    • Al Roker not only is a Jackass Genie, but he tricked Penny into signing the adults over to him so he can enslave them in his sweatshop and then he tricks Penny into betting the twins to be his slaves as well.
    • Helga from “Thelma and Luis” is revealed to be running a slave labor camp for elderly people.
    • Sista Spice at first seems like a typical con artist, until she reveals that she was gonna have Oscar take the fall in her scam.
  • 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.
  • Tangled: The Series reveals that Gothel crossed it long before her MEH in the movie. While making off with the baby Rapunzel, she left her actual daughter, Cassandra, alone with the guards who were tailing her. This moment becomes the root cause for Cass's betrayal at the end of season 2, brought on by Zhan Tiri's manipulation.
  • 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.
  • 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".

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