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.
Lord Vyce crosses over when he MindRapes NIMUE, forcing Linkara to delete her. At this point, we can pretty much drop the "Anti" part of Anti-Villain.
NIMUE:You areevil Vyce. You are cruel and unjust.
Bennett the Sage goes into discussion about this in his End of Evangelion review, in regards to the opening minutes. He discusses how it can make an effective Anti-Hero, but in Shinji's case it was just...well let's have Shinji describe it.
I'm so fucked up.
Dr. Horrible's Sing-Along Blog 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 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 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.
The most despicable character in Gotham Girls, a web-exclusive tie-in to the DCAU, is surprisingly not any of the supervillains but rather 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.
Alex in Marble Hornets 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 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 he's been doing it for years, even back when he was making the original Marble Hornets movie.
Parodied in-universe by The Nostalgia Chick'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 Captive Date, 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 Paperwalls crossed this when he raped his daughter Cameron, and kept finding new moral event horizons to cross.
Wyoming was Affably Evil all along, but for some viewers he seems to have crossed the line beyond any sympathy when he 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 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. 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 she had done the same thing to her twin brother, she went from 'bitch' to 'irredeemable bitch'. And the reason for that last incident? He got an AI, and she didn't.
And finally (notice these are all Freelancers?), if Agent Washington actually did kill Donut at the end of Recreation, that will almost certainly be his own moral event horizon. No, hedidn'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 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 Felix, of all people, gets one. After ordering Tucker to throw him a grenade meant for Locus, Felix tells the Reds and Blues that he and Locus are 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 kill every single person on the planet.
The Season 12 finale ultimately gives this to "Control", the mysterious employer of Locus and Felix. While their plans were already morally reprehensible, The Reveal that his identity is Malcolm Hargrove, aka the Chairman, makes this worse when you take his prior actions into account.
The SCP Foundation: "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 Moral Event Horizon is that 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)... and then they do it again...
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 True Companions 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, Carol Burke, after Carol said she wasn't as strong as she thought she was.Disproportionate Retribution much?
It also turns out to be an in-universe example; When Reiko comes across her girlfriend Sarah Xu and 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 Sarah and Reiko being separated. Ouch.
Maxwell Lombardi strangling Augustus MacDougal, shooting Harold Fisher, and gloating to the cameras that there was more where that came from. Which there was.
Alex White crosses the line with his slow, torturous killing of Rosa Fiametta.
Aaron Hughes crosses it, but most agree that 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 Manipulative Bastard 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 Super Mario Bros. Z 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 There Will Be Brawl when she stabbed Link in the back just as he was making a Heel-Face Turn, then in the next episode revealed that she had been working with Gannondorf the whole time. Not even attempting to take the bullet for Link redeemed her, really.
Wario. 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 To Boldly Flee, the Executor was a sleazy, manipulative, creepy Bad Boss and Magnificent Bastard, 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. Thankfully he did.
In We Are Our Avatars, Carter/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 his getting kicked off the team and re-defecting to the rest of the group.
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 BlackMage.
Deviot revived Kasei. Worked out till Saturn's version of Him decided to give Kasei his power back.
Jeff The Killer crossed the point of no return by killing his entire family.
The Terrible Trio responsible for his Start of Darkness, 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.
The titular antagonist crossed the line either when he destroyed the Yogcave or when he zombified Granny_Bacon, forcing Lewis Brindley and Simon Lane to put her down, later bombing her funeral. The latter is often cited by fans as his point of no return.
Jock_Fireblast crosses the line when he burns down Mistral City.
Skylord_Vitali murdering his comrades in increasingly brutal, gruesome and nightmarish ways also counts, all for the sake of power.
King_Finbar crossed the line when he zombified his own subjects, even those loyal to him.
From Sjin's "Feed the World" series, eventual Knight of Cerebus Strawfingers is revealed to have crossed the line through Cerebus Retcon, when it turns out he murdered Abel's parents.
The Yoglabs series by and large revolves around a Mad Scientist group experimenting, but there are nevertheless some particularly horrendous moments that are taken deadly seriously.
Gozencrantz and Rildenstern cross the line when they murder Simon's master clone in an effort to take over Yoglabs.
As of "Block Gun Mod", Lewis appears to have crossed the line by ordering Simon to blow up a village of Testificates with the weaponry from the titular mod. The tone of his voice implies that unlike previous efforts, the villagers are sentient and it isn't just a simulation like before. This causes Simon to blow up a large chunk of the lab and try to free some trapped commandos that were insane, though he gets himself and most of the hostages killed in the attempt. Due to the cloning system, Simon doesn't remember this.