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    Heisei Phase 1 Series 
  • Kamen Rider Ryuki:
    • Sudo firmly cements his villainy after taking advantage of Shinji's trust and getting information on Ren, he sics Volcancer on Ren. Later he revealed to have crossed it before he ever appeared given that he routinely sicked Volcancer on anybody he didn't like.
    • Jun already showed himself to a bastard, but he managed to one up himself when he planned to use ORE journal to set up a nation wide version of his deranged game that drove people to murder each other.
    • As a child, Asakura set fire to his own house and killed his parents in attempt to kill his little brother because he found him annoying.
    • Tojo crosses it when he kills Kagawa, believing that sacrificing those closest to him made a hero.
  • Kamen Rider 555:
    • Yuka's younger half-sister, Michiko, crossed it by making their parents believe that Yuka injured her and got her kicked out of the family by their father even though she didn't do anything wrong, then having her friends take her shoes and socks off and tearing them during their game.
    • The Owl Orphnoch crossed it by targeting his best students because he saw humans unfit to have such talent greater than his own, and believed that those who sought to live by the talents of their hands should live harsh lives, thus being the one also responsible for destroying Kaido's musical talent.
    • Among all the callous manipulations he pulled, Kusaka crossed the line by inconspicuously becoming Faiz and fighting Kiba in hopes of breaking his friendship with Takumi, even lying to the latter when he asked what happened with Kiba.
    • Masahiko Minami crossed it twice by trying to have his forces take Yuka in to experiment on her and also keeping the Crab Orphnoch another of his experiments.
    • Saeko crossed it by killing Yuka while the latter was weakened from Minami's police forces attacking her, Takumi, and Kiba.
    • If being responsible for the attack at the Ryusel School reunion wasn't enough, then Kitazaki certainly crossed it by trying to attack their king as another of his games even though the latter was still a kid at the time, not even caring that it would result in the end of his race, in hopes of becoming the new king.
  • Kamen Rider Blade:
    • If Isaka didn't cross it by making Tachibana soak in Schuld Kestner seaweed to be his brainwashed warrior or kidnap teenage boys to see who would be compatible with the Leangle Buckle, then he certainly crossed it when he killed Sayoko for trying to clean up her lover and disregarding his warning to her.
    • Shinmei crossed it by making Kenzaki, Tachibana, and the rest of the Undead Hunters complete the Black Fang, killing off the latter crew once he declared that they were of no further use for him.
    • Tennoji crossed it by intentionally unsealing all the Undead in hopes that the Riders reseal them for him while he makes an artificial Undead that would help him win his engineered Battle Fight and his aspirations of godhood.
  • Kamen Rider Kabuto: Mishima crossed the line twice by keeping Dark Kabuto a captive prisoner/experiment subject for years and helping Negishi turn the populace into Natives through the armlets given to those numerous innocents.
  • Kamen Rider Den-O: If being cruel to Ryutaros wasn't enough, then Kai certianly crossed it by making an Imagin army out of his remaining memories to wipe out time after finding out that Sukurai wasn't the key to the Junction Point.
  • Kamen Rider Kiva:
    • King crossed the line by making Maya remain to him through the threat of him planning to kill infant Taiga. Even Kivat-bat the 2nd was disgusted at King's mistreatment.
    • Bishop crossed the line not only by secretly killing Mio and making Wataru believe he did it, but also trying to resurrect King through reviving an army of Fangires to attack society after Taiga kicked him out of his life upon stupidly telling him that he was Mio's true murderer.
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    Heisei Phase 2 Series 
  • Kamen Rider Double:
    • If the powers of the Utopia Dopant don't convince you that Jun is a monster, then the fact that he went after Shotaro and Philip's friends and sucked their faces off will convince you to want to see Jun get his ass handed to.
    • The Spider Dopant killing a multitude of people by spreading bombs which will kill the one their host loves the most when they touch all over the city, likely racking up the highest death count in the series. Narumi even tells him that he crossed the line with that action.
    • Commander kidnapping Akiko with the intention to kill her in front of Terui to make Terui the copy of him. The fact she's an innocent person who has done nothing wrong is what makes him cross the line.
    • Two words: "Heaven's Fall".
  • Kamen Rider OOO:
    • Kazari using Gamel and Mezool in an experiment that could quite obviously be fatal and not caring one bit both were killed in the result. In fact, he smiles while he observes his handywork.
    • If he didn't cross it by locking his assistants in a lab with rampaging Yummy For Science!, Dr. Maki crossed this when he realizes he murdered his own sister and reacts, not with remorse, but by deciding he did the right thing by killing her and now it's time to destroy the world. It's more likely the latter, as before that point, he wasn't beyond redemption. It's this point that it becomes clear he's irredeemable. Made even worse by the tensing of a Heel–Face Turn directly before it.
    • Eiji's father crossed this by exploiting the fact his son was badly wounded and emotionally scarred for life by a war his family's money funded to get votes! How could anyone blame Eiji for walking out on his family after that?
  • Kamen Rider Fourze:
    • Hiroki Makise, the Pyxis Zodiarts, crosses this by blowing up the locker serving as the Rabbit Hutch for no other reason but to make Yuki cry, knowing full well it's vitally important to her (and after that calling her 'damaged goods'). If that didn't send him over this, trying to murder a bus full of innocent people certainly does.
      • What's worse? Those innocent people were the girls he stalked before he went after Yuki. There must've been around 20 girls that were in that bus (Miu being one of them). Now factor in on how he went giving Yuki all those letters, gifts, and voicemails...God, I feel chills down my spine...
    • Misa Toriizaki gets one for forcing Eguchi to become the Cygnus Zodiarts despite Eguchi knowing what would happen to him. Made worse when the Ugly Ducklings also go with it, chanting "Cygnus!" as Eguchi screams in terror and then those Ducklings start worshiping him.
    • It will seem pretty hard for Ryusei to be likeable for effectively becoming the Hero Killer and causing some heartbreak in Kengo. Especially considering the other option he had. Even he believes he crossed it and tries to redeem himself. He succeeds and even becomes Gentaro's friend.
    • Rem in Movie Wars Megamax crosses this line when he takes Nadeshiko and turns her into the SOLU Switch, pretty much killing her, even going as far as to state that he "killed" her.
    • Virgo Zodiarts crosses the MEH three times in one episode when she's revealed to be Emoto. The first MEH is leaving Rokuro for dead on the moon. The second is invoking the Heel–Face Door-Slam on Sugiura. And the third one that kicked him far past the MEH is sending Tomoko to the Dark Nebula. He doesn't know when he's crossed it however, and the next episode after, he threatens the KRC with death unless they leave the club, then sends Ryusei to the Dark Nebula after he reveals that he's also Tachibana.
      • SUBVERTED! he actually was a double-agent, and he didnt send then to the dark nebula, but hide them in the M-bus to protect them, including Tomoko and Ryusei.
    • Libra and Leo both cross this when they downright force Yuki of all people to become a Horoscopes.
    • The reveal of Gamou's endgame pushes him across it.
      • Though, if you wish to interpret it as such, all three Zodiarts crossed the horizon when they kill Emoto.
      • Gamou really crosses this by not caring one bit that Libra gave his life for his.
    • Gemini when she tricks the Kamen Rider Club into nearly killing Yuuki. She'd win in 10 hours anyway, she outright says she did this For the Evulz.
  • Kamen Rider Wizard:
    • If Phoenix didn't cross it when he nearly killed Hiroki's parents, then he definitely did it when he tried to burn Rinko alive after convincing him to stop taking orders from the Big Bad.
    • Medusa crossed hers in one fell swoop, first by revealing to her Gate's sister that she killed her parents and caused her to cross the Despair Event Horizon, and then by preventing Haruto from helping Mayu and forcing him to watch as she succumbs to despair.
    • Gremlin/Sora passed his in his backstory before he became a Phantom with the revelation that he was a sociopathic Serial Killer. His moment afterwards? How about killing Koyomi?
      • If not there, he definitely crossed it be going on a rampage through Tokyo, on the rationale that the Gates will be driven into despair and become Phantoms and the normal humans will just die. What makes it worse is how much Gremlin's clearly enjoying every second of it.
    • Where was Wiseman's, you ask? Was it when he turned his own daughter into a vessel for the Philosopher's Stone? Creating the Phantoms in the first place? Holding the Sabbath? Manipulating everyone and causing countless murders and deaths for the sake of making Phantoms and Wizards? By that point, kidnapping someone a kid is the equivalent to jaywalking for him.
  • Kamen Rider Gaim:
    • Kaito crosses it by siccing Inves on defenseless civilians and by wanting the helheim invasion to happen that would cause billions of people to die.
    • Sid personally crosses by killing Hase, especially since he was the one who led him to his downfall by giving him the Sengoku Driver, though even Takatora knew that, hence why he let Sid do the job.
    • Ryoma crosses by allowing Sid to kill Kouta in #21, knowing full well that Sid despises everything about Kouta, if only to enhance his research. If he didn't cross it then, then he certainly has near the end game by manipulating Micchy to kill Kouta and while he's doing that, proceed to kill Mai by extracting the golden fruit from her.
    • If the two haven't crossed the line in some viewer's eyes with those moments, then the revelation in #22 will. Yggdrasill's master plan involves making as many Sengoku Drivers as they possibly can so people can survive without having to eat Helheim fruit - but they'll only be able to make a belt for one out of every seven people on Earth. The catch is that this isn't merely trying but failing to save everyone, they plan to actively kill six-sevenths of the world population to bring the numbers down to what they can save. Ryoma and Sid hit the event horizon by not only being perfectly okay with this, but by also considering it as a small step towards their overall plans; Takatora holds himself back from crossing it since he seems to know how horrible it is, even if he considers it a Necessary Evil.
      • What's worse is Ryoma knew about the Overlord Inves for what seemed to be years, and didn't reveal it purely because he wanted the Forbidden Fruit and to spite Takatora for rejecting his ideals. The guy knew of another option for a long time and kept it to himself because he wanted power.
    • Mitsuzane crossed his in the late-20s episodes when he first set up an ambush to literally shoot Kouta in the back when he was vulnerable, then stood by and consented to the murder of his own brother and stole his Driver to impersonate Zangetsu Shin and shoot down any hopes Kouta had of finding an ally. The question about him used to be "Is he still trying to protect Kouta and Mai and just misguided, or is he too caught up in his secrets to see straight anymore?"; now it's "Did he ever genuinely care, or was he Evil All Along?"
      • His attempted (and possibly successful) murder of Takatora in #36 might be considered another one, if you didn't think he was already capable of it by then. It's at the very least a Sanity Event Horizon, as committing that action seems to have broken his little mind completely.
      • He may have crossed it earlier for some people in #17, where he almost got Kouta's sister, an innocent bystander, mixed up in the war in an attempt to get Kouta's belt, going so far as to have someone personally assault her, who probably would have went through with it had it not been for Oren's interference.
    • Rosyuo devastating America with the Macross Missile Massacre, followed by unleashing Inves all over the world to slaughter innocent people. After that, it's hard to feel any 'anti-villain' traits for that damn monster, even after how he proclaims that he'll give humanity a chance. YMMV, though, as he was just redirecting the missles that America (and other countries) fired on him, and he genuinely feels he's doing humanity a favor by giving us a Mercy Kill.
    • If waging war on public television wasn't enough, then Redyue certainly crossed it with betraying Rosyuo in an attempt to get the Forbidden Fruit, and when that was revealed to be a fake, she starts assaulting him into telling her the location of the actual fruit, ending with her killing her king when he dodges away from her demanding.
  • Kamen Rider Drive:
    • Most people can agree that Medic's crossed this line upon killing a Roidmude who proves that they can coexist with humans and then stating that she'll proceed to cull the rest of the Roidmudes save for herself, Heart, and a select few. But then she just keeps going.
      • If not then, Medic certainly crossed it once she began experimenting on her own kind. Notably, this act ended up making Heart openly furious with her, even more furious than he's been with Drive up until now.
    • The killer of Shinnosuke's father had crossed this a long time ago, as Nira did it out of envy. Just because Eisuke Tomari tried to help him. If they discount past events, then the lengths he went to cover it up, including putting the girl that Eisuke died to save in mortal peril (in his own words, 'it would mean that your father had died for nothing') would.
      • Same goes for Brain for going along with it, ensuring said mortal peril in the first place.
    • Banno crossed it way before the series even began by using his own subject as a punching bag. If they discount past events, then him attempting to kill Gou and labeling him a failure will.
    • You don't have too be affiliated with the Roidmudes to cross this, as So Utsuki, AKA the Judge, crossed it by murdering Toma Okajima and framing him for his own crimes. Why? Because Toma helped him, and So can't stand someone saving him.
    • Roidmude 005, while originally a one-off villain, comes out on his own as a villain by crossing this in Mach's side story, in which he manipulates girls into killing their fathers with their own hair, effectively tearing families apart, all while emotionally abusing his template's daughter, who just wanted to live in peace, by forcing her to play a game of cat and mouse and breaking her so hard that she considered killing herself.
  • Kamen Rider Ex-Aid:
    • Once he's revealed to be evil, Masamune slowly creeps towards the line until he's crossed it and things can only gets worse from there.
    • Taiga of all people crosses this in Episode 8 when he kidnaps the Bugster, forcing Emu and Hiiro to fight him in order to save a completely innocent person's life, followed immediately by him going Level 3 to bring death from above to the two, and finally baiting Ex-Aid, who is completely focused on saving the patient's life, with the Bugster so that he can More Dakka him to oblivion.
    • Kuroto's actions during the series were without a doubt heinous, but once it's revealed that he infected Emu with the Bugster Virus as a child for sending him fan mail with ideas as good as his own, it becomes clear that he's crossed it a long time ago and has only been sinking lower ever since.
    • Parado crosses this when he kills Kuroto by infecting him with a lethal dosage of the Bugster Virus. Any other situation, this would qualify as both a case of Bad Guys Do the Dirty Work and Kick the Son of a Bitch but the problem is that Kuroto was already rendered a non-threat by the time Parado got to him. Though if you think that's not that bad, he gleefully skips across the horizon by completing Kamen Rider Chronicle and announcing its true intent: human extinction, apparently to show them what it means to be beaten like him.
      • In the same episode, Parado kills six users of Kamen Rider Chronicle who had no idea what was really going on or how much danger they were in. None of them stood any chance against him whatsoever, basically taking his talk about fair play and throwing it in the dumpster. Then again, if he didn't want to play fair, he could always just kill everyone he sees instead of just the people who play Kamen Rider Chronicle.
  • Kamen Rider Build:
    • Blood Stalk/Evolt crosses it when its revealed that he orchestrated the death of Ryuga's girlfriend specifically to hurt him and is planning to end all life on the planet. And then there's the fact that he's already done it countless times before all for the sake of power. He only stopped at Mars because he was too damaged by Vernage to continue.
    • While turning Ryuga's girlfriend into a Smash despite knowing she wouldn't survive just to hurt him was a horrific act, Night Rogue really crosses this by stealing Pandora's Box with the full intent of setting off all out war between the three factions Japan has been split up into, an act which could potentially cause a lot of innocent deaths. It's later deconstructed after he becomes Kamen Rider Rogue. Said act was performed while he was under the influence of the Pandora Box and persuasion from the Blood Tribe (as revealed in The Movie), and when raising his Hazard Level to use the Sclash Driver broke that influence, the sheer guilt over what he's done, combined with the hellish training he endured, turns him into a Shell-Shocked Veteran who believes himself beyond redemption. It's only until much later that the heroes manage to convince him that he can still become a hero.
    • Namba crossed the line decades before the series started once it was revealed that he created a unit of brainwashed child spies expected to serve him for life and kill themselves if they failed or just weren't needed anymore.
    • Utsumi crosses it when he goes insane and pledges his loyalty to Evolt, knowing full well that he plans to destroy the world. Even when it is revealed that it was just an act so that Utsumi could get a hold of an Evol Driver so that he could personally avenge Namba.
  • Kamen Rider Zi-O:
    • Oma Zi-O, Sougo’s future self from the 2068 timeline, already crossed it before (or after?) the series by invading the world through giant destructive robots and cutting the entire world's population in half thus turning the world into a Crapsack World.
    • Swartz crossed it by kidnapping a bus filled with children to force one of them to develop the potential to become Oma Zi-O by placing them in a future of destruction and taking the survivors.
    • Ora crosses it by revealing she was in on Swartz’s plan on using Heure to become Another Kikai, and had it not been for Zi-O II, Ora’s actions would have gotten Tsukuyomi killed by the feral Another Kikai. Though if that doesn't do it, then maybe actually killing Yuko once she's loses her powers as Another Kiva (no matter how much she may have mistreated her and the other Time Jackers) will. Eventually, she goes as far as to kill Heure in cold blood, even after all he’d done to save her in spite of her treating him as little more than a tool for Swartz’s plans. Surprisingly enough, the last one is subverted as she basically meant for it to be a Mercy Kill to keep up an appearance with Swartz, when she actually planned on using her regained powers to kill him as well for using them both as his pawns.
    • White Woz definitely crossed it with him turning Amane into Another Blade so that it would start a chain of events that would result in the Undead Battle Fight resuming and ending the world after absorbing Blade and Chalice’s powers, leaving her the last Joker standing. Why? Because the chances for the Geiz Revive timeline is finished, making him in danger of getting a Ret-Gone, so if he doesn’t have a future, no one else should.
    • According to Tsukuyomi, Black Woz originally crossed it when he betrayed the resistance group that he himself was in charge of to Oma Zi-O, resulting in her and Geiz being the only survivors.
    • In episode 41, Hiryu, instead of learning to forgive Sougo, chooses to become Another Zi-O once more, subjects the world under a tyrannical rule and harms millions of people just to spite Sougo. In Final Stage, he still goes for one last attempt by taking over Quartzer as the new Barlckxs to collect the Showa Ridewatches, ultimately becoming Another Oma Zi-O. Now planning to wipe out the Heisei era altogether because he feels he shouldn't have been born in it.

    Reiwa Series 
  • Kamen Rider Zero-One:
    • Any thoughts of MetsubouJinrai.NET having a noble goal for HumaGears are quashed by their horrific treatment of them.
    • Horobi has one in Episode 6 when Jin can't actually bring himself to turn a certain HumaGear into the Monster of the Week, so he responds by forcefully reprogramming Jin, revealed to be HumaGear himself, into doing it anyway.
    • Gai Amatsu crossed it before any of them considering he's responsible for giving the Ark its mentality which gave rise to MetsubouJinrai.NET and them in the first place. If that wasn't enough to prove he jumped into the horizon, then ep.29 showed he cannonballed into multiple moral event horizons by mentally torturing Fuwa with the AI chip in his head and not batting a single eye doing so while the latter is screaming in pain. And he doesn't even let up after he throws the Rampage Gatling Key at him. The episode also shows how he doesn't even care about the well-being of other people, seeing them as merely tools that must follow his directives all to further his agenda in controlling Hiden Intelligence.
    • As crosses it for orchastrating the events that lead to the deaths of Is and Jin in order to corrupt Aruto and Horobi into a new incarnation of the Ark, while also potentially causing an all-out war between humanity and Humagears.

    Spinoffs 
  • Kamen Rider Amazons:
    • The Nozama higher ups (except Reika, who's at least TRYING to clean up their mess as best she can) cross this with The Reveal of why they're covering up the Amazons' existence: solely to keep the Amazon Cells' their own property. 4,000 man-eating monsters are allowed to secretly rampage across the country with a seven member team being the only ones assigned to deal with them, all because a bunch of Corrupt Corporate Executives want to keep something to themselves for profit. The fact many of them consider the Peston Service 'not cost effective' when they're already grossly understaffed and struggling adds to this.
    • Takaaki Tenjo crossed it when he intentionally released the aboved mentioned 4,000 man-eating monsters to create his own mini-ecosystem.
    • Mamoru also crossed the line when he started to used one of the Origin's limbs to spread the lysogenic cells on the water source to infect humans and turn them into the New-type Amazons as a retaliation towards humanity.
    • Tachibana and 4C by proxy in The Last Judgement, all too willing to create and groom artificial Amazon children to be cultivated and sold to the rich out of petty rage toward the practically-extinct Amazons under the justification of a "meat shortage."
  • Kamen Rider Dragon Knight: When Kit finally realizes Torque's been playing him like a fiddle the whole time, Drew smugly admits it and then vents Camo, a potential ally to his cause, in cold blood.

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