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[[quoteright:240:[[WebAnimation/SuperMarioBrosZ http://static.tvtropes.org/pmwiki/pub/images/mecha_sonic_kills_tails_8198_8341.png]]]]
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* ''WebVideo/AtopTheFourthWall'': Mechakara firmly crossed it when he [[spoiler: tried to [[DrivenToSuicide drive Linkara to suicide]] (and it was ''not'' PlayedForLaughs), by making him think he was [[AbusiveParents the father]] of the girl who was turned into his magic gun.]]
** [[spoiler:Holokara pulled an extreme FaceHeelTurn and drove over the horizon in a single move, when he ''[[AxCrazy threatened to kill '90s Kid]] if he ever [[DisproportionateRetribution interrupted the show again.]]'']] Definitely '''not''' PlayedForLaughs.
** [[spoiler: He crosses it again later when he threatens to maim Harvey Finevoice when Harvey calls him out for threatening to kill '90s Kid. Specifically, he casually threatens to crush the singer's vocal chords.]]
** [[spoiler: Lord Vyce]] crosses over when he [[spoiler: {{MindRape}}s NIMUE, forcing Linkara to delete her. At this point, we can pretty much drop the "Anti" part of AntiVillain.]]
--> '''NIMUE:''' ''You are'' '''''evil''''' ''[[spoiler: Vyce]]. You are cruel and unjust.''
* BennettTheSage goes into discussion about this in his ''[[Anime/NeonGenesisEvangelion End of Evangelion]]'' review, in regards to the opening minutes. He discusses how it can make an effective AntiHero, but in Shinji's case it was just...well let's have Shinji describe it.
-->I'm so fucked up.
* DrHorriblesSingAlongBlog has an odd example, as the 'hero' of the story passes his before the villain does. Furthermore, he is responsible for the villain's MEH. Captain Hammer's is viewed by many as [[spoiler: bragging to Billy that he is going to sleep with Penny solely because he knows Billy has a crush on her.]] However, if this doesn't qualify, his decision to [[spoiler: use the Death Ray on Dr. Horrible in a room full of innocent people definitely does. This results in Penny's death, which tips Billy over the edge.]]
* In the ''GlobalGuardiansPBEMUniverse'', the [[OmnicidalManiac Blood Red King]] is the AnthropomorphicPersonification of Cruelty and Malice, and as such he came into being already well past the MoralEventHorizon. His worst act to date was walking into a hospital in Amsterdam and killing every doctor, nurse, patient, administrator, janitor, visitor, and newborn infant whose last name began with an "odd numbered letter" (A = 1, B = 2, and so on), leaving the rest alive and traumatized. Why did he do this? [[ButForMeItWasTuesday Because he was bored on a Wednesday]].
* The most despicable character in ''WebAnimation/GothamGirls'', a web-exclusive tie-in to the {{DCAU}}, is surprisingly not any of the supervillains but rather [[TyrantTakesTheHelm Acting Commissioner Greenway]]. Throughout the series she commits numerous violations of police ethics, notably trying to kill criminals from the get-go instead of attempting to arrest them first, but the point at which we realize how twisted she is is when, after Commissioner Gordon returns and she has to step down, she takes out her rage by ordering Catwoman, Harley, and Ivy beaten to death in prison. Thankfully, they escape.
* ''WebVideo/TheIrateGamer'' [[DesignatedHero himself]] murdering Kool-Aid Man for doing what he does on Christmas.
** In the ''Franchise/StarTrek: 25th Anniversary'' review, he kills [[RedShirt Lieutenant Drunkard]] by beaming him down onto Apandana, a planet with gaseous atmosphere. [[DisproportionateRetribution All because he was insulted.]]
-->'''[[http://irategamersucks.blogspot.com/2013/05/my-sensors-indicate-massive-amounts-of.html BatDanNight]]:''' Holy shit! That was needlessly cruel! I know the character was annoying and I even predicted he would die (red shirt) but I didn't expect it to be that awful! I thought it would be a Gorn or a Klingon or something. [[WhatTheHellHero You're the hero! You’re not supposed to do this!]]
* Alex in ''MarbleHornets'' was always a bit unhinged. Breaking Tim's leg, refusing to tell Jay anything, lying to everyone he knows. But the line was crossed in Entry #49 when [[spoiler: he murdered an innocent man just checking to see if he's okay, believing it was Jay following him. He then has The Operator dispose of the body.]] No hope now.
** Entry #51 reveals [[spoiler: he's been doing it for years, even back when he was making the original Marble Hornets movie.]]
*** Even then, [[spoiler: Alex's motivation was questionable, due to the possibility of The Operator [[BrainwashedAndCrazy being around his entire childhood.]]]] However, [[spoiler: Hoodie/[[TheReveal ToTheArk]] really went JumpingOffTheSlipperySlope in Entry #61, where he sabotages Tim's medication and causes him to revert back into Masky.]] Damn.
* Parodied in-universe by WebVideo/TheNostalgiaChick's Dark Nella Saga. The Chick only realizes Dark Nella is evil when she finds that Minnesota's big ball of twine has been destroyed. Oh no!
** With the Todd storyline, Chick became a concretely psychotic stalker at one of three instances. Either forcing him regularly to be her CaptiveDate, being too happily willing to rape him, or preying on his money insecurities to make him do a review with her; take your pick.
* William Shaw in ''Literature/{{Paperwalls}}'' crossed this when he raped his daughter Cameron, and kept finding new moral event horizons to cross.
* In RedVsBlue, the default characterization is UnsympatheticComedyProtagonist, so it's a little hard to pinpoint any particularly heinous events. Still, a few characters have gotten these, especially since CerebusSyndrome has set in:
** Wyoming was AffablyEvil all along, but for some viewers he seems to have crossed the line beyond any sympathy when he [[spoiler:killed York]]. That was in a mini-series, though, so not everyone's familiar with the event.
** Tex came very close to crossing the horizon when she proved willing to [[spoiler:kidnap Tucker's son Junior and use him to sabotage the aliens' religion, ending the war by genociding the other race]]. She didn't slip over only because the plan, much like her ship, barely got off the ground, and the goal now seems firmly out of reach. [[spoiler:She's also been dead now for longer than she's ever been before, which seems to mitigate the effect somewhat.]]
** Agent South Dakota had already shot one partner in the back, and tried to sacrifice the AI Delta, both to save her own skin. But when Delta then revealed that [[spoiler:she had done the same thing to her [[HalfIdenticalTwins twin brother]]]], she went from 'bitch' to 'irredeemable bitch'. And the reason for that last incident? [[spoiler:[[CainAndAbel He got an AI, and she didn't.]]]]
** And finally (notice these are all Freelancers?), if Agent Washington actually did [[spoiler:kill Donut]] at the end of ''Recreation'', that will almost certainly be his own moral event horizon. [[spoiler: [[WordofGod No]], [[FakingTheDead he]] [[{{Retcon}} didn't.]]]]
** With Season 10 rolling out, Sigma, Maine's AI seems to have gone down this path. He, along with Gamma, coerce Carolina to taking two AI's so she could beat [[AlwaysSomeoneBetter Texas]], he manipulates Maine into becoming the Meta, and is, in essence, responsible for Project Freelancer's infighting and eventual implosion.
** Come Season 12, and [[spoiler:''[[EvilAllAlong Felix]]'', of all people, gets one. After ordering Tucker to throw him a grenade meant for [[ConsummateProfessional Locus]], Felix tells the Reds and Blues that he and Locus are [[TeethClenchedTeamwork still working together]] and were hired, not by their respective factions in the planetary civil war, but by an unknown third party. Not only that, they're not trying to end the war, they're trying to ''prolong'' it so they can ''[[KillEmAll kill every single person on the planet]]''.]]
* The [[NoNameGiven mysterious]] [[EvilSorcerer mage]] of ''TheQuestportChronicles'' jumps straight across when he [[spoiler:destroys Questport]]. To make matters worse, the heroes still aren't sure ''why'' he did it.
* ''The Wiki/SCPFoundation:'' "[[http://scp-wiki.wikidot.com/scp-590 SCP-590]] is not to be named as anything other then Five Ninety. He is a tool to be used, not someone's friend, sibling, or child. Anyone found forming attachments to an SCP will be removed to a less people-intensive duty." A teenage boy who has the power to heal any human ailment by touching someone and taking the ailment to himself. The way the Foundation took advantage of this is infecting him with mental retardation to keep him pliable. Where they ''really'' cross the MoralEventHorizon is that [[spoiler:the person who suggested it, Dr. Bright, is ''his older brother.'']]
** There's also SCP-231-7 and the containment process for her, 110-Montauk, which is [REDACTED]. It's so horrible that anyone who performs it gets mind-wiped (if they don't commit suicide first)... [[AndIMustScream and then they do it again]]...
** Even worse, this is a NecessaryEvil ([[EvenEvilHasStandards They don't want to preform the procedure on SCP-231-7]], but she will give birth to a [[EldritchAbomination monster that is said to bring forth the end of time]] if they don't). The Foundation doesn't really believe in a MoralEventHorizon.
* Various villains in ''SurvivalOfTheFittest'' cross this line at some point:
** Cody Jenson was already a dick before, but after his rape and murder of Madelaine Shirohara, followed by killing Amanda Jones while trying to kill Sidney Crosby, the SOTF community in general rallied behind Adam Dodd, whose TrueCompanions the two girls were part of, to kill him.
** Adam Reeves manages to cross this line in his very first appearance, after raping Maxie Dasai.
** After killing 5 people, Reiko Ishida still managed to cross this line after killing defenseless girl and only living friend, [[spoiler:Carol Burke, after Carol said she wasn't as strong as she thought she was.]] DisproportionateRetribution much?
*** It also turns out to be an in-universe example; When Reiko comes across her girlfriend Sarah Xu and [[spoiler:attempts to get on the escape boat with her, she is denied access to the boat by STAR, who then proceeds to use, among other things, the above incident for a reason why.]] It results in [[spoiler:Sarah and Reiko being separated]]. [[HeelFaceDoorSlam Ouch]].
** Maxwell Lombardi strangling Augustus [=MacDougal=], shooting Harold Fisher, and gloating to the cameras that there was more where that came from. [[FromBadToWorse Which there was]].
** Alex White crosses the line with his [[spoiler:slow, torturous killing of Rosa Fiametta]].
** Aaron Hughes crosses it, but most agree that [[spoiler:leaving Tom Guthrie to die at the hands of Nick Reid and then claiming he died to protect the group]] very early on in the game was quite cruel and confirmed the character to be a ManipulativeBastard in most handlers' eyes.
** Marvia Jones in SOTF-TV managed to cross it in her first in-game appearance, when she comes across a traumatized Nate Chauncey. She then proceeds to give her ecstasy (which she tells her is a headache pill) and take advantage of her sexually. It culminates it her calling Nate a whore for accepting her advances, beating her up, and stealing most of her supplies, including her clothes.
* Mecha Sonic from ''WebAnimation/SuperMarioBrosZ'' crashes the Death Egg into Mobius, murders Tails, Amy, Rogue, Omega, Knuckles, Cream, and Cheese simply to fulfill his bloodlust, and turns the planet into a burning wasteland. And this was after he was just created once he merged with several other Metal Sonics. He finds more lines to cross afterwards.
* Of all people, ''Princess Zelda'' crossed this in ''ThereWillBeBrawl'' when she [[spoiler: stabbed Link in the back just as he was making a HeelFaceTurn, then in the next episode revealed that she had been working with Gannondorf the whole time. Not even attempting to [[TakingTheBullet take the bullet]] for Link redeemed her, really.]]
** Wario. [[spoiler: He orchestrated a Pikmin Bomb to take out Red (the only indisputably ''good'' character in the series, got his mentally challenged brother to deliver the bomb, and then tried to pay Red's girlfriend off with money (and that was a lie; he had planned to kill her too).]]
** Kirby crosses this in the backstory when he gruesomely murders Daisy.
* Throughout WebVideo/ToBoldlyFlee, the Executor was a sleazy, manipulative, creepy BadBoss and MagnificentBastard, but he was hammy. But then he tortured a helpless Luke (one of the youngest members of the site) with his electricity powers and you wanted him to die painfully. [[spoiler: Thankfully he did]].
* In Roleplay/WeAreOurAvatars, [[Series/PowerRangersLightspeedRescue Carter]]/[[GenderBender Catherine]] doesn't just cross this after becoming a Team Rocket member, s/he leaps directly over it, starts running, and never looks back. This eventually leads to hir getting kicked off the team and re-defecting to the rest of the group.
** [[VideoGame/MegaManBattleNetwork Duo]] mentions an incident with Slur involving seven planets being destroyed, he notes that 5 of those planets may not have been infected with Evil Energy in the first place, and that Slur may have done it just because she could.
** Cyber Amy(A.K.A. Amy being fused with her father Deviot's soul) rapes [[Webcomic/EightBitTheater Black]] [[TheChewToy Mage]].
** Deviot revived Kasei. Worked out till Saturn's version of Him decided to give Kasei his power back.
* Madgie telling her sister she should [[http://akaichounokoe.deviantart.com/art/Maybe-I-will-380946348 go kill herself]]
* JeffTheKiller crossed the point of no return by killing his entire family.
** The TerribleTrio responsible for his StartOfDarkness, Randy, Keith, and Troy, crossed it by attacking Jeff at a party and threatening to shoot the party goers if they tried to stop them from killing Jeff.
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