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*** Exclusively in the LightNovel, her first crossing can be seen when she was grumbling on how disobedient Astolfo was for saving Sieg in the first place. A homunculus passed by her torture room, merely being in the wrong place and the wrong time, and when Celenike noticed this, she ordered the homunculus to come inside the room... and [[ForTheEvulz proceeded to gruesomely murder that homunculus because she can.]]
to:
*** Exclusively in the LightNovel, her first crossing can be seen when she was grumbling on how disobedient Astolfo was for saving Sieg in the first place. A homunculus passed by her torture room, merely being in the wrong place and the wrong time, and when Celenike noticed this, she ordered the homunculus to come inside the room... and [[ForTheEvulz proceeded to gruesomely murder that homunculus because she can.]]]] If you had any doubts that Celenike was a nasty piece of work, this scene should more than lay those doubts to rest.
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** Kirei is highly complex, and whether or when he crossed it in ''Fate/Zero'' can be debated, but [[spoiler:his murder of Tokiomi (though some see him as an AssholeVictim) who deeply trusted him, could count]]... however, where he ''really'' seals the deal is when [[spoiler: he uses Tokiomi's corpse to drive a wedge between Aoi and Kariya ForTheEvulz, which ends up in the latter strangling the former.]]
to:
** Kirei is highly complex, and whether or when he crossed it in ''Fate/Zero'' can be debated, but [[spoiler:his murder of Tokiomi (though some see him as an AssholeVictim) who deeply trusted him, could count]]... however, where he ''really'' seals the deal is when [[spoiler: he uses Tokiomi's corpse to drive a wedge between Aoi and Kariya ForTheEvulz, which ends up in the latter strangling the former.former, and renders Aoi crippled and with severe brain damage in the aftermath.]]
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** Celenike crosses it as well. [[spoiler: While in the midst of a VillainousBreakdown, she uses her Command Spells to force Astolfo, her Servant, into killing Sieg. Her reason? Astolfo was getting too attached to the homunculus he saved, and she intended to [[KickTheDog make him drown in despair]] him by making him break his code of honor by forcing him to murder an innocent person, something only stopped by Mordred lopping off Celenike's head. Celenike only saw Astolfo as her familiar, meaning in her mind, she owned him and could do what she wanted with him, even [[BreakTheCutie break him mentally]]. For that matter, having a master like [[{{Sadist}} Celenike]] is any good-natured and honorable Servant's worst nightmare.]]
to:
** Celenike crosses it as well. [[spoiler: While in the midst of a VillainousBreakdown, she uses her Command Spells to force Astolfo, her Servant, into killing Sieg. Her reason? Astolfo was getting too attached to the homunculus he saved, and she intended to [[KickTheDog make him drown in despair]] him by making him break his code of honor by forcing him to murder an innocent person, something only stopped by Mordred lopping off Celenike's head. Celenike only saw Astolfo as her familiar, meaning in her mind, she owned him and could do what she wanted with him, even [[BreakTheCutie break him mentally]]. For that matter, having a master like [[{{Sadist}} Celenike]] is any good-natured and honorable Servant's worst nightmare.]]
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** When Kirei was introduced in this verse, there's a lot who thought that he might take a backseat of being a bad guy, since Koyanskaya has been rather heavy in showing that she's going to be the villain by doing [[KickTheDog lots of dog-kicking.]] [[spoiler:After it was revealed that he was in cahoots with Koyanskaya, Kirei showed that he's still the good ol' sociopathic wild card villainous priest we all know and 'love' by [[ImpaledWithExtremePrejudice fatally impaling Da Vinci with his bare hand]].]]
** Beryl cements himself as the TokenEvilTeamMate of the Crypters when he [[spoiler: betrays and fatally wounds Wodime simply because if Wodime's plan succeeded, he would be unable to kill people anymore]]. It also doesn't help that ''before'' this, he was also [[spoiler:''very, very creepy'' regarding Mash, to the point of breaking into Mash's room and breaking her fingers just to get her to show something]].
** Beryl cements himself as the TokenEvilTeamMate of the Crypters when he [[spoiler: betrays and fatally wounds Wodime simply because if Wodime's plan succeeded, he would be unable to kill people anymore]]. It also doesn't help that ''before'' this, he was also [[spoiler:''very, very creepy'' regarding Mash, to the point of breaking into Mash's room and breaking her fingers just to get her to show something]].
to:
** When Kotomine Kirei was introduced in this verse, there's a lot who thought that he might take a backseat of being a bad guy, since Koyanskaya has been rather heavy in showing that she's going to be the villain by doing [[KickTheDog lots of dog-kicking.]] [[spoiler:After it was revealed that he was in cahoots with Koyanskaya, Kirei showed that he's still the good ol' sociopathic wild card villainous priest we all know and 'love' by [[ImpaledWithExtremePrejudice fatally impaling Da Vinci with his bare hand]].]]
** Beryl Gut cements himself as the TokenEvilTeamMate of the Crypters when he [[spoiler: betrays and fatally wounds Wodime simply because if Wodime's plan succeeded, he would be unable to kill people anymore]]. It also doesn't help that ''before'' this, he was also [[spoiler:''very, very creepy'' regarding Mash, to the point of breaking into Mash's room and breaking her fingers just to get her to show something]].
** Beryl Gut cements himself as the TokenEvilTeamMate of the Crypters when he [[spoiler: betrays and fatally wounds Wodime simply because if Wodime's plan succeeded, he would be unable to kill people anymore]]. It also doesn't help that ''before'' this, he was also [[spoiler:''very, very creepy'' regarding Mash, to the point of breaking into Mash's room and breaking her fingers just to get her to show something]].
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** Beryl cements himself as the TokenEvilTeamMate of the Crypters when he [[spoiler: betrays and fatally wounds Wodime simply because if Wodime's plan succeeded, he would be unable to kill people anymore]]. It also doesn't help that ''before'' this, he was also [[spoiler:
''very, very creepy'' regarding Mash, to the point of breaking into Mash's room and breaking her fingers just to get her to show something]].
''very, very creepy'' regarding Mash, to the point of breaking into Mash's room and breaking her fingers just to get her to show something]].
to:
** Beryl cements himself as the TokenEvilTeamMate of the Crypters when he [[spoiler: betrays and fatally wounds Wodime simply because if Wodime's plan succeeded, he would be unable to kill people anymore]]. It also doesn't help that ''before'' this, he was also [[spoiler:
''very,[[spoiler:''very, very creepy'' regarding Mash, to the point of breaking into Mash's room and breaking her fingers just to get her to show something]].
''very,
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** Beryl cements himself as the TokenEvilTeamMate of the Crypters when he [[spoiler: betrays and fatally wounds Wodime simply because if Wodime's plan succeeded, he would be unable to kill people anymore]]. It also doesn't help that ''before'' this, he also [[spoiler:he was ''very, very creepy'' regarding Mash, to the point of breaking into Mash's room and breaking her fingers just to get her to show something]].
to:
** Beryl cements himself as the TokenEvilTeamMate of the Crypters when he [[spoiler: betrays and fatally wounds Wodime simply because if Wodime's plan succeeded, he would be unable to kill people anymore]]. It also doesn't help that ''before'' this, he was also [[spoiler:he was [[spoiler:
''very, very creepy'' regarding Mash, to the point of breaking into Mash's room and breaking her fingers just to get her to show something]].
''very, very creepy'' regarding Mash, to the point of breaking into Mash's room and breaking her fingers just to get her to show something]].
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** Celenike crosses it as well. [[spoiler: While in the midst of a VillainousBreakdown, she uses her Command Spells to force Astolfo, her Servant, into killing Sieg. Her reason? Astolfo was getting too attached to the homunculus he saved, and she intended to [[KickTheDog make him drown in despair]] him by making him break his code of honor by forcing him to murder an innocent person. She only saw Astolfo as her familiar, meaning in her mind, she owned him and can do what she wants with him, even [[BreakTheCutie break him mentally]]. For that matter, having a master like Celenike is any good natured and honorable Servant's worst nightmare.]]
*** Exclusively in the Light Novel, her first crossing can be seen when she was grumbling on how disobedient Astolfo was for saving Sieg in the first place. A homunculus passed by her torture room, merely being in the wrong place and the wrong time, and when Celenike noticed this, she ordered the homunculus to come inside the room... and [[ForTheEvulz proceeded to gruesomely murder that homunculus because she can.]]
*** Exclusively in the Light Novel, her first crossing can be seen when she was grumbling on how disobedient Astolfo was for saving Sieg in the first place. A homunculus passed by her torture room, merely being in the wrong place and the wrong time, and when Celenike noticed this, she ordered the homunculus to come inside the room... and [[ForTheEvulz proceeded to gruesomely murder that homunculus because she can.]]
to:
** Celenike crosses it as well. [[spoiler: While in the midst of a VillainousBreakdown, she uses her Command Spells to force Astolfo, her Servant, into killing Sieg. Her reason? Astolfo was getting too attached to the homunculus he saved, and she intended to [[KickTheDog make him drown in despair]] him by making him break his code of honor by forcing him to murder an innocent person. She person, something only stopped by Mordred lopping off Celenike's head. Celenike only saw Astolfo as her familiar, meaning in her mind, she owned him and can could do what she wants wanted with him, even [[BreakTheCutie break him mentally]]. For that matter, having a master like Celenike [[{{Sadist}} Celenike]] is any good natured good-natured and honorable Servant's worst nightmare.]]
*** Exclusively in theLight Novel, LightNovel, her first crossing can be seen when she was grumbling on how disobedient Astolfo was for saving Sieg in the first place. A homunculus passed by her torture room, merely being in the wrong place and the wrong time, and when Celenike noticed this, she ordered the homunculus to come inside the room... and [[ForTheEvulz proceeded to gruesomely murder that homunculus because she can.]]
*** Exclusively in the
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** Beryl cements himself as the TokenEvilTeamMate of the Crypters when he [[spoiler: betrays and fatally wounds Wodime simply because if Wodime's plan succeeded, he would be unable to kill people anymore.]]
to:
** Beryl cements himself as the TokenEvilTeamMate of the Crypters when he [[spoiler: betrays and fatally wounds Wodime simply because if Wodime's plan succeeded, he would be unable to kill people anymore.]]anymore]]. It also doesn't help that ''before'' this, he also [[spoiler:he was ''very, very creepy'' regarding Mash, to the point of breaking into Mash's room and breaking her fingers just to get her to show something]].
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** For a lot of fans, Lev Lainur crossed this very early with his gruesome murder of Olga Marie. It was enough that during the Solomon Singularity, [[spoiler:he (as Demon Pillar Flauros) is usually next in line to be obliterated by the players after [[ButtMonkey Barbatos]] to avenge Olga Marie and despite the global players knowing from the Japanese versions some good things he did for Chaldea and later against Solomon/Goetia himself, that still didn't earn him any forgiveness for Olga Marie's murder.]]
to:
** For a lot of fans, Lev Lainur crossed this very early on not only by sabotaging the Rayshift experiment and blowing up the Command Room (which not only killed a good number of Chaldea's people but required Mash to make a contract and become a Demi-Servant just to survive and also killed Director Olga Marie who was at ground zero), but going the extra mile by sending poor Olga on a crash course with his gruesome murder Chaldeas, which had the effect of tearing her apart on a physical and spiritual level, essentially condemning her to "infinite living death" -- one of the worst fates ever suffered by a Nasuverse character, and one that Olga Marie.doesn't even come ''close'' to deserving. It was enough that during the Solomon Singularity, [[spoiler:he (as Demon Pillar Flauros) is usually next in line to be obliterated by the players after [[ButtMonkey Barbatos]] to avenge Olga Marie and despite the global players knowing from the Japanese versions some good things he did for Chaldea and later against Solomon/Goetia himself, that still didn't earn him any forgiveness for Olga Marie's murder.]]
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** As of Episode 23, Shakespeare using his Noble Phantasm First Folio [[spoiler: to MindRape Jeanne. First, he uses his illusions to create scenarios, like her mother begging her not to go to war, or making her see the dead soldiers blame her for their deaths, but these have no effect on her. That is until the third scenario, where it is pictured almost exactly like the time she was burned at the stake, except, he makes it so its Sieg who gets burned and tells her that this event is her fault. This effects Jeanne visibly, but she doesn't break. The final scenario, where her old friend and comrade in arms, Gilles de Rais shows up, with Seig's severed head, and gives her a massive BreakingSpeech about how she really loves the poor lad, when she is supposed to a love everyone equally as Saint, while slowly transforming into his murderously insane self in the process. By the look of satisfaction on his face, [[TheSociopath Shakespeare]] probably knew the first two scenarios wouldn't work on Jeanne, but did them anyway simply to test her, before moving on to acts three & four to really [[BreakTheCutie break her spirit]].]] Indeed, he likes writing tragedies.
to:
** As of Episode 23, Shakespeare using his Noble Phantasm First Folio [[spoiler: to MindRape Jeanne. First, he uses his illusions to create scenarios, like her mother begging her not to go to war, or making her see the dead soldiers blame her for their deaths, but these have no effect on her. That is until the third scenario, where it is pictured almost exactly like the time she was burned at the stake, except, he makes it so its Sieg who gets burned and tells her that this event is her fault. This effects Jeanne visibly, but she doesn't break. The final scenario, where her old friend and comrade in arms, Gilles de Rais shows up, with Seig's Sieg’s severed head, and gives her a massive BreakingSpeech about how she really loves the poor lad, when she is supposed to a love everyone equally as Saint, while slowly transforming into his murderously insane self in the process. By the look of satisfaction on his face, [[TheSociopath Shakespeare]] probably knew the first two scenarios wouldn't work on Jeanne, but did them anyway simply to test her, before moving on to acts three & four to really [[BreakTheCutie break her spirit]].]] Indeed, he likes writing tragedies.
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* ''VisualNovel/Tsukihime'':
to:
* ''VisualNovel/Tsukihime'': ''VisualNovel/{{Tsukihime}}'':
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MoralEventHorizon in the Franchise/Nasuverse.
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MoralEventHorizon in the Franchise/Nasuverse.Franchise/{{Nasuverse}}.
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Add from MoralEventHorizon/VisualNovels and respective YMMV pages
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MoralEventHorizon in the Franchise/Nasuverse.
!!''[[Franchise/FateSeries Fate Series]]''
* ''VisualNovel/FateStayNight''
** [[spoiler:Shinji Matou]] ''starts out'' as a {{Jerkass}}, but crosses the line in every route. In ''Fate'' it's [[spoiler:trying to kill off the entire school to power up his Servant]]; his laughing in ''Unlimited Blade Works'' [[spoiler:as Gilgamesh rips Ilya's heart out is cruel, but with his AttemptedRape on Tohsaka he crosses the line]]. And then we find out in ''Heaven's Feel'' that he's [[spoiler:raped his sister Sakura many, many times before the story begins]].
** [[spoiler:Zouken Matou]] who has a massive head start on everyone else in this area as his actions [[spoiler:cause Shinji and Sakura's misery among many others]], with by far his worst acts involving [[spoiler:the use of his horrible parasitic worms on Sakura. When she was ''still a child'']]. It's quite telling that ''Kotomine'' of all people considers this guy a very nasty piece of work.
** [[EnfantTerrible Illyasviel von Einzbern]] crosses the line in many {{Downer Ending}}s, particularly the ones in ''Fate'' and ''Heaven's Feel'' where she has Berserker decapitate Shirou, but [[FateWorseThanDeath still keeps him alive so that she can torture him even more]] or [[AndIMustScream transfers Shirou's soul into a doll to "keep" him]].
** [[spoiler:Kotomine Kirei using the orphans of the Fuyuki City fire as [[AndIMustScream living prana batteries]] for Gilgamesh]], though we only find out about it in the ''Fate'' route. [[spoiler:And this could very well have happened to Shirou.]]
** [[spoiler:Gilgamesh himself]], if his description of what he plans on doing to Saber in the ''Fate'' route isn't sickening enough, he crosses it by [[spoiler:[[EyeScream destroying Ilya's eyes]] and ripping her heart out]] without a shred of remorse in ''Unlimited Blade Works''.
** The "Superhero" DownerEnding in ''Heaven's Feel'' where [[spoiler:Shirou pragmatically allows Sakura to die to save many people]], considering [[WhatTheHellHero everyone's reactions]], might be an InUniverse example.
** The "Geas" BadEnd in ''Heaven's Feel'' has [[spoiler:Rin Tohsaka cross it. In this ending, Shirou swears his absolute obedience to Rin, and she's all too willing to use that against him, subjecting him to a nasty MindRape when he tries to go against her decision and save Sakura. The implications this has on Shirou are horrific to say the least, as the ending monologue strongly implies that he ends up losing his sanity.]]
** In ''Heaven's Feel'' [[spoiler:Sakura Matou herself]] has unknowingly summoned a Shadow that is killing and devouring hundreds of people, and [[spoiler:after killing Shinji for trying to rape her,]] she succumbs to the Shadow's influence and believes that she is beyond saving. However, it's only when [[spoiler:Sakura brutally tortures Rin in the "Femme fatale" Bad End]], that ''Shirou'' ([[spoiler:who has sacrificed everything for her]]) realizes that she's too far gone to be saved. And in ''Fate/unlimited codes'' her dark side crosses this by [[spoiler:keeping Bazett alive just so she can watch her suffer]].
* ''Anime/FateStayNightUnlimitedBladeWorks'':
** Archer definitely crossed the line when he [[spoiler:left Rin completely helpless so that Shinji could rape her]]. This is more of a case of AdaptationalVillainy, as Archer (despite everything) [[spoiler:had every intention of protecting her in the VN, but was left with only 10% of his power after his fight against Saber, thus leaving him unable to make a proper stand against the clearly-antipathic Gilgamesh; this makes it understandable that he would have to make the decision to pursue his plan to kill Shirou over getting killled by Gilgamesh and leaving Rin unprotected either way. However, with the anime throwing that entire detail into question due to Archer still being able to materialize Unlimited Blade Works (a reliable counter to the Gate of Babylon) against Shirou, it really makes Archer's actions seem a lot colder by comparison.]]
** Gilgamesh takes a flying leap over the horizon with [[spoiler:his brutal beatdown and murder of Illya.]]
* ''Literature/FateZero'':
** In-universe example: Saber confronts Kiritsugu about crossing it when he [[spoiler:forces Kayneth to have his own Servant, whom Saber respected, commit suicide, and then has the broken and defeated Kayneth and Sola-Ui shot by Maiya, killing the latter and leaving the former begging for it to end, which Saber herself has to grant]]; Kiritsugu justifies it by invoking NecessarilyEvil and WarIsHell. Also an out-of-universe example, for some.
** Ryuunosuke Uryuu's ''[[EstablishingCharacterMoment very first scene]]'' has him happily finishing up murdering a family. It's not even his first murder, just his first onscreen one.
** Caster also crosses this line in record time, by killing a child after giving him [[HopeSpot a brief moment of hope]] '''one minute''' after summoning.
** Kirei is highly complex, and whether or when he crossed it in ''Fate/Zero'' can be debated, but [[spoiler:his murder of Tokiomi (though some see him as an AssholeVictim) who deeply trusted him, could count]]... however, where he ''really'' seals the deal is when [[spoiler: he uses Tokiomi's corpse to drive a wedge between Aoi and Kariya ForTheEvulz, which ends up in the latter strangling the former.]]
* ''Literature/FateApocrypha'':
** Darnic crosses it [[spoiler:when he forces Vlad by Command Seal to [[OneWingedAngel transform into Dracula]] and then [[DemonicPossession forcibly possess him]] after Vlad kills him in retaliation. What pushes this over IDidWhatIHadToDo (since Darnic did it with the express purpose of getting the Greater Grail back and there was no other way they could force their way through to get it and Vlad would have preferred death to transforming) is [[KickTheDog how much pleasure Darnic takes in reveling in the power of Dracula and mocking Vlad for trying to get in the way of his ambition]]]].
** Celenike crosses it as well. [[spoiler: While in the midst of a VillainousBreakdown, she uses her Command Spells to force Astolfo, her Servant, into killing Sieg. Her reason? Astolfo was getting too attached to the homunculus he saved, and she intended to [[KickTheDog make him drown in despair]] him by making him break his code of honor by forcing him to murder an innocent person. She only saw Astolfo as her familiar, meaning in her mind, she owned him and can do what she wants with him, even [[BreakTheCutie break him mentally]]. For that matter, having a master like Celenike is any good natured and honorable Servant's worst nightmare.]]
*** Exclusively in the Light Novel, her first crossing can be seen when she was grumbling on how disobedient Astolfo was for saving Sieg in the first place. A homunculus passed by her torture room, merely being in the wrong place and the wrong time, and when Celenike noticed this, she ordered the homunculus to come inside the room... and [[ForTheEvulz proceeded to gruesomely murder that homunculus because she can.]]
** In the very next episode, Avicebron/Caster of Black crossed it by [[spoiler:sacrificing his own Master Roche to complete his Golem, despite his screams of anguish of being betrayed by his own Servant/professor, which subverts his reasoning to the Red Faction about defecting to them as long as his Master is unharmed, because he'll be the one who does the 'harming' ''personally'', for his own goal of recreating Paradise since he dislikes mankind, and in his own words, it has nothing to do with the Holy Grail at all. So all along, he's on neither side.]] He seals it with his own words, "You have every right to hate me.", and now you see why the normally affable professor is amongst the more amoral characters in both factions. Not only Chiron eventually offs him for this fact, the Throne of Heroes eventually would make sure that [[OnceDoneNeverForgotten he'd never live this act down]], engraving the scene into Avicebron's Saint Graph that after he was summoned in *''VideoGame/FateGrandOrder'', even he agreed that it was very unforgivable and [[MyGreatestFailure shamed himself for even thinking of doing that.]]
** As of Episode 23, Shakespeare using his Noble Phantasm First Folio [[spoiler: to MindRape Jeanne. First, he uses his illusions to create scenarios, like her mother begging her not to go to war, or making her see the dead soldiers blame her for their deaths, but these have no effect on her. That is until the third scenario, where it is pictured almost exactly like the time she was burned at the stake, except, he makes it so its Sieg who gets burned and tells her that this event is her fault. This effects Jeanne visibly, but she doesn't break. The final scenario, where her old friend and comrade in arms, Gilles de Rais shows up, with Seig's severed head, and gives her a massive BreakingSpeech about how she really loves the poor lad, when she is supposed to a love everyone equally as Saint, while slowly transforming into his murderously insane self in the process. By the look of satisfaction on his face, [[TheSociopath Shakespeare]] probably knew the first two scenarios wouldn't work on Jeanne, but did them anyway simply to test her, before moving on to acts three & four to really [[BreakTheCutie break her spirit]].]] Indeed, he likes writing tragedies.
* ''Literature/FateStrangeFake'': What Tsubaki's parents did to her, sweet Jesus! You'd think they see what kind of person Zouken was, but nope, they decided to use their daughter as a test subject!
* ''VideoGame/FateGrandOrder'':
** For a lot of fans, Lev Lainur crossed this very early with his gruesome murder of Olga Marie. It was enough that during the Solomon Singularity, [[spoiler:he (as Demon Pillar Flauros) is usually next in line to be obliterated by the players after [[ButtMonkey Barbatos]] to avenge Olga Marie and despite the global players knowing from the Japanese versions some good things he did for Chaldea and later against Solomon/Goetia himself, that still didn't earn him any forgiveness for Olga Marie's murder.]]
** When Kirei was introduced in this verse, there's a lot who thought that he might take a backseat of being a bad guy, since Koyanskaya has been rather heavy in showing that she's going to be the villain by doing [[KickTheDog lots of dog-kicking.]] [[spoiler:After it was revealed that he was in cahoots with Koyanskaya, Kirei showed that he's still the good ol' sociopathic wild card villainous priest we all know and 'love' by [[ImpaledWithExtremePrejudice fatally impaling Da Vinci with his bare hand]].]]
** Beryl cements himself as the TokenEvilTeamMate of the Crypters when he [[spoiler: betrays and fatally wounds Wodime simply because if Wodime's plan succeeded, he would be unable to kill people anymore.]]
!!Other media
*''Literature/TheGardenOfSinners'': Cornelius Alba was never an especially sympathetic character, but after he starts [[spoiler:parading Touko's head around like a trophy, then torments Mikiya with it and then starts beating an unconscious Mikiya's head ''into the wall'']] he has to die.
* ''VisualNovel/Tsukihime'':
** Makihisa Tohno seems to embody this in just about everything he does, despite being a PosthumousCharacter.
** Also from the manga, we get a depiction of what happened to Ciel after she revived from being killed by Arcueid while possessed by Roa. Basically, the Church attempting to 'correct' as what they saw as an unnatural body, had her killed at least ''six hundred times'' including such deaths as by drowning, burning and organ removal, the whole time as she begged them to stop, only quitting when they decided she'd be more useful as a Burial agent. Afterwards, Ciel is shown as completely broken and resigned.
!!''[[Franchise/FateSeries Fate Series]]''
* ''VisualNovel/FateStayNight''
** [[spoiler:Shinji Matou]] ''starts out'' as a {{Jerkass}}, but crosses the line in every route. In ''Fate'' it's [[spoiler:trying to kill off the entire school to power up his Servant]]; his laughing in ''Unlimited Blade Works'' [[spoiler:as Gilgamesh rips Ilya's heart out is cruel, but with his AttemptedRape on Tohsaka he crosses the line]]. And then we find out in ''Heaven's Feel'' that he's [[spoiler:raped his sister Sakura many, many times before the story begins]].
** [[spoiler:Zouken Matou]] who has a massive head start on everyone else in this area as his actions [[spoiler:cause Shinji and Sakura's misery among many others]], with by far his worst acts involving [[spoiler:the use of his horrible parasitic worms on Sakura. When she was ''still a child'']]. It's quite telling that ''Kotomine'' of all people considers this guy a very nasty piece of work.
** [[EnfantTerrible Illyasviel von Einzbern]] crosses the line in many {{Downer Ending}}s, particularly the ones in ''Fate'' and ''Heaven's Feel'' where she has Berserker decapitate Shirou, but [[FateWorseThanDeath still keeps him alive so that she can torture him even more]] or [[AndIMustScream transfers Shirou's soul into a doll to "keep" him]].
** [[spoiler:Kotomine Kirei using the orphans of the Fuyuki City fire as [[AndIMustScream living prana batteries]] for Gilgamesh]], though we only find out about it in the ''Fate'' route. [[spoiler:And this could very well have happened to Shirou.]]
** [[spoiler:Gilgamesh himself]], if his description of what he plans on doing to Saber in the ''Fate'' route isn't sickening enough, he crosses it by [[spoiler:[[EyeScream destroying Ilya's eyes]] and ripping her heart out]] without a shred of remorse in ''Unlimited Blade Works''.
** The "Superhero" DownerEnding in ''Heaven's Feel'' where [[spoiler:Shirou pragmatically allows Sakura to die to save many people]], considering [[WhatTheHellHero everyone's reactions]], might be an InUniverse example.
** The "Geas" BadEnd in ''Heaven's Feel'' has [[spoiler:Rin Tohsaka cross it. In this ending, Shirou swears his absolute obedience to Rin, and she's all too willing to use that against him, subjecting him to a nasty MindRape when he tries to go against her decision and save Sakura. The implications this has on Shirou are horrific to say the least, as the ending monologue strongly implies that he ends up losing his sanity.]]
** In ''Heaven's Feel'' [[spoiler:Sakura Matou herself]] has unknowingly summoned a Shadow that is killing and devouring hundreds of people, and [[spoiler:after killing Shinji for trying to rape her,]] she succumbs to the Shadow's influence and believes that she is beyond saving. However, it's only when [[spoiler:Sakura brutally tortures Rin in the "Femme fatale" Bad End]], that ''Shirou'' ([[spoiler:who has sacrificed everything for her]]) realizes that she's too far gone to be saved. And in ''Fate/unlimited codes'' her dark side crosses this by [[spoiler:keeping Bazett alive just so she can watch her suffer]].
* ''Anime/FateStayNightUnlimitedBladeWorks'':
** Archer definitely crossed the line when he [[spoiler:left Rin completely helpless so that Shinji could rape her]]. This is more of a case of AdaptationalVillainy, as Archer (despite everything) [[spoiler:had every intention of protecting her in the VN, but was left with only 10% of his power after his fight against Saber, thus leaving him unable to make a proper stand against the clearly-antipathic Gilgamesh; this makes it understandable that he would have to make the decision to pursue his plan to kill Shirou over getting killled by Gilgamesh and leaving Rin unprotected either way. However, with the anime throwing that entire detail into question due to Archer still being able to materialize Unlimited Blade Works (a reliable counter to the Gate of Babylon) against Shirou, it really makes Archer's actions seem a lot colder by comparison.]]
** Gilgamesh takes a flying leap over the horizon with [[spoiler:his brutal beatdown and murder of Illya.]]
* ''Literature/FateZero'':
** In-universe example: Saber confronts Kiritsugu about crossing it when he [[spoiler:forces Kayneth to have his own Servant, whom Saber respected, commit suicide, and then has the broken and defeated Kayneth and Sola-Ui shot by Maiya, killing the latter and leaving the former begging for it to end, which Saber herself has to grant]]; Kiritsugu justifies it by invoking NecessarilyEvil and WarIsHell. Also an out-of-universe example, for some.
** Ryuunosuke Uryuu's ''[[EstablishingCharacterMoment very first scene]]'' has him happily finishing up murdering a family. It's not even his first murder, just his first onscreen one.
** Caster also crosses this line in record time, by killing a child after giving him [[HopeSpot a brief moment of hope]] '''one minute''' after summoning.
** Kirei is highly complex, and whether or when he crossed it in ''Fate/Zero'' can be debated, but [[spoiler:his murder of Tokiomi (though some see him as an AssholeVictim) who deeply trusted him, could count]]... however, where he ''really'' seals the deal is when [[spoiler: he uses Tokiomi's corpse to drive a wedge between Aoi and Kariya ForTheEvulz, which ends up in the latter strangling the former.]]
* ''Literature/FateApocrypha'':
** Darnic crosses it [[spoiler:when he forces Vlad by Command Seal to [[OneWingedAngel transform into Dracula]] and then [[DemonicPossession forcibly possess him]] after Vlad kills him in retaliation. What pushes this over IDidWhatIHadToDo (since Darnic did it with the express purpose of getting the Greater Grail back and there was no other way they could force their way through to get it and Vlad would have preferred death to transforming) is [[KickTheDog how much pleasure Darnic takes in reveling in the power of Dracula and mocking Vlad for trying to get in the way of his ambition]]]].
** Celenike crosses it as well. [[spoiler: While in the midst of a VillainousBreakdown, she uses her Command Spells to force Astolfo, her Servant, into killing Sieg. Her reason? Astolfo was getting too attached to the homunculus he saved, and she intended to [[KickTheDog make him drown in despair]] him by making him break his code of honor by forcing him to murder an innocent person. She only saw Astolfo as her familiar, meaning in her mind, she owned him and can do what she wants with him, even [[BreakTheCutie break him mentally]]. For that matter, having a master like Celenike is any good natured and honorable Servant's worst nightmare.]]
*** Exclusively in the Light Novel, her first crossing can be seen when she was grumbling on how disobedient Astolfo was for saving Sieg in the first place. A homunculus passed by her torture room, merely being in the wrong place and the wrong time, and when Celenike noticed this, she ordered the homunculus to come inside the room... and [[ForTheEvulz proceeded to gruesomely murder that homunculus because she can.]]
** In the very next episode, Avicebron/Caster of Black crossed it by [[spoiler:sacrificing his own Master Roche to complete his Golem, despite his screams of anguish of being betrayed by his own Servant/professor, which subverts his reasoning to the Red Faction about defecting to them as long as his Master is unharmed, because he'll be the one who does the 'harming' ''personally'', for his own goal of recreating Paradise since he dislikes mankind, and in his own words, it has nothing to do with the Holy Grail at all. So all along, he's on neither side.]] He seals it with his own words, "You have every right to hate me.", and now you see why the normally affable professor is amongst the more amoral characters in both factions. Not only Chiron eventually offs him for this fact, the Throne of Heroes eventually would make sure that [[OnceDoneNeverForgotten he'd never live this act down]], engraving the scene into Avicebron's Saint Graph that after he was summoned in *''VideoGame/FateGrandOrder'', even he agreed that it was very unforgivable and [[MyGreatestFailure shamed himself for even thinking of doing that.]]
** As of Episode 23, Shakespeare using his Noble Phantasm First Folio [[spoiler: to MindRape Jeanne. First, he uses his illusions to create scenarios, like her mother begging her not to go to war, or making her see the dead soldiers blame her for their deaths, but these have no effect on her. That is until the third scenario, where it is pictured almost exactly like the time she was burned at the stake, except, he makes it so its Sieg who gets burned and tells her that this event is her fault. This effects Jeanne visibly, but she doesn't break. The final scenario, where her old friend and comrade in arms, Gilles de Rais shows up, with Seig's severed head, and gives her a massive BreakingSpeech about how she really loves the poor lad, when she is supposed to a love everyone equally as Saint, while slowly transforming into his murderously insane self in the process. By the look of satisfaction on his face, [[TheSociopath Shakespeare]] probably knew the first two scenarios wouldn't work on Jeanne, but did them anyway simply to test her, before moving on to acts three & four to really [[BreakTheCutie break her spirit]].]] Indeed, he likes writing tragedies.
* ''Literature/FateStrangeFake'': What Tsubaki's parents did to her, sweet Jesus! You'd think they see what kind of person Zouken was, but nope, they decided to use their daughter as a test subject!
* ''VideoGame/FateGrandOrder'':
** For a lot of fans, Lev Lainur crossed this very early with his gruesome murder of Olga Marie. It was enough that during the Solomon Singularity, [[spoiler:he (as Demon Pillar Flauros) is usually next in line to be obliterated by the players after [[ButtMonkey Barbatos]] to avenge Olga Marie and despite the global players knowing from the Japanese versions some good things he did for Chaldea and later against Solomon/Goetia himself, that still didn't earn him any forgiveness for Olga Marie's murder.]]
** When Kirei was introduced in this verse, there's a lot who thought that he might take a backseat of being a bad guy, since Koyanskaya has been rather heavy in showing that she's going to be the villain by doing [[KickTheDog lots of dog-kicking.]] [[spoiler:After it was revealed that he was in cahoots with Koyanskaya, Kirei showed that he's still the good ol' sociopathic wild card villainous priest we all know and 'love' by [[ImpaledWithExtremePrejudice fatally impaling Da Vinci with his bare hand]].]]
** Beryl cements himself as the TokenEvilTeamMate of the Crypters when he [[spoiler: betrays and fatally wounds Wodime simply because if Wodime's plan succeeded, he would be unable to kill people anymore.]]
!!Other media
*''Literature/TheGardenOfSinners'': Cornelius Alba was never an especially sympathetic character, but after he starts [[spoiler:parading Touko's head around like a trophy, then torments Mikiya with it and then starts beating an unconscious Mikiya's head ''into the wall'']] he has to die.
* ''VisualNovel/Tsukihime'':
** Makihisa Tohno seems to embody this in just about everything he does, despite being a PosthumousCharacter.
** Also from the manga, we get a depiction of what happened to Ciel after she revived from being killed by Arcueid while possessed by Roa. Basically, the Church attempting to 'correct' as what they saw as an unnatural body, had her killed at least ''six hundred times'' including such deaths as by drowning, burning and organ removal, the whole time as she begged them to stop, only quitting when they decided she'd be more useful as a Burial agent. Afterwards, Ciel is shown as completely broken and resigned.
