History MoralEventHorizon / SailorMoon

** Esmeraude [[spoiler:leaves Rubeus to die on his exploding ship in Episode 74. Leaving Rubeus to die when he actually seemed to trust her would be despicable... if Rubeus hadn't done the exact same thing to the Four Sisters, which makes Esmeraude's actions more an example of KickTheSonOfABitch than anything]].

** Before you feel bad about Jaedite, though, he crossed it earlier in the same season with his attempt on Tuxedo Kamen's life in his own last episode. Just as bad as Zoicite's aforementioned attempt, but what makes this one stand out is that he proceeds to taunt the Sailor Senshi about it. It's also an InUniverse example, as instead of doing as he had predicted, the Sailor Senshi promptly make their disgust known, both [[YouMonster verbally]] ''and'' [[CarFu physically]].[[spoiler: The Shitenou may not qualify however having been brainwashed by the Queen and not in real control over their actions.]]

** Wiseman crosses this when he [[spoiler:corrupts the [[WellIntentionedExtremist well-meaning yet extreme goals]] of the Black Moon people and their leader Dimande. Unlike Rubeus, Saphir [[HeelFaceTurn eventually got wise to Wiseman's act]], but Wiseman [[RedemptionEqualsDeath kills him]] just as he's about to show Dimande the light as well. [[BigBrcotherInstinct Dimande is not amused, and it only hastens the inevitable.]]]] And then it's clinched when [[spoiler: he kidnaps Chibi-Usa when [[HeroicBSOD in a particularly low point]], then giving her FakeMemories ''and'' [[MindRape forcibly infusing her with black energy]], which turns her into Black Lady.]]

* The manga counterparts of the Sailor Animamates - who lack the redeeming qualities of their anime counterparts - crossed this a long ago when they murdered the Guardians of their home planets.

[[caption-width-right:350:"Well if someone is inside the display unit when the power of the machine is shut off, they would be automatically sealed inside it forever."]]

** Tellu crosses it with how she [[AndIMustScream deals with Mimete]]. To put it in perspective, ''Sailor Moon herself'' is horrified to see one of her nemeses being dealt with in such a callous fashion. Damn... when a ''hero'' is mortified by the death of a villain (who could've killed the good guys, including him/her, with a single blow, mind you) at the hands of another villain, you know the killer in question has crossed a line.

!! ''Franchise/SailorMoon''

* Nehellenia in the manga crossed this when she forcibly awakened the Sailor Quartet. And unlike her anime counterpart she was not redeemed and is evil incarnate (literally).

** Jaedite crossed it earlier in the same season with his attempt on Tuxedo Kamen's life in his own last episode. Just as bad as Zoicite's aforementioned attempt, but what makes this one stand out is that he proceeds to taunt the Sailor Senshi about it. It's also an InUniverse example, as instead of doing as he had predicted, the Sailor Senshi promptly make their disgust known, both [[YouMonster verbally]] ''and'' [[CarFu physically]].[[spoiler: The Shitenou may not qualify however having been brainwashed by the Queen and not in real control over their actions.]]
** Zoicite gets his chance by stabbing Tuxedo Kamen in the back lethally, purely ForTheEvulz, before they start their honor duel. Even worse, it's revealed he was aiming for Sailor Moon, after Zoicite had promised to leave her out of the fight, against Sailor Moon's protests because she says they have to work together to defeat him.

** In the ''R'' movie, the Kisenian Flower corrupts a young Fiore, implied to be one of the Doom Tree's children, and makes him obsessed with returning to Mamoru. Any time Mamoru or the Senshi try to talk reason into Fiore by pointing out his actions would be destroying the planet and hurting innocent people, the Kisenian Flower brainwashes him into denying their reality. It wants him to destroy the planet with its flowers, whispering that Sailor Moon deceives everyone into loving her. No one can get a clear shot on the Kisenian Flower without hurting Fiore, making it even worse; in the end, Fiore destroys the Kisenian by sheer HeroicWillpower and a HeelRealization.

** Mistress 9 crossed this when she swallows Chibiusa's pure heart, thus condemning her host's best friend to death. What's worse is that Hotaru is fighting back the whole time, knowing what's going to happen, and she eventually succumbs when Chibiusa is captured and strapped to an altar. As soon as Hotaru frees herself, her first action is to return the pure heart.

** Telulu crosses it with how she [[AndIMustScream deals with Mimet]]. To put it in perspective, ''Sailor Moon herself'' is horrified to see one of her nemeses being dealt with in such a callous fashion. Damn... when a ''hero'' is mortified by the death of a villain (who could've killed the good guys, including him/her, with a single blow, mind you) at the hands of another villain, you know the killer in question has crossed a line.

** Dimande crossed this not by kidnapping Sailor Moon and depowering her -- that was actually pretty practical-- but by dressing her in a facsimile of Neo-Queen Serenity's gown and using magic to immobilize her when she slaps him away.

** The DD Girls cross it by using dirty tricks to outright ''murder'' the Senshi. They're the only youma with a kill count, because they use illusions. Then when Usagi begs for them to spare Minako. It's quite satisfying when we see Mars roast two at once with her dying breath.

* TheNineties ''Manga/SailorMoon'' has a few of them:
** In the first season, for example, Queen Beryl has many acts that could easily qualify for this trope. She [[spoiler: caused the War that ended with many ruined lives and Endymion and Serenity's death and rebirth]] and years afterwards she brings Metalia into power in order to cause an Apocalypse. The way to do it is by collecting the life essence of various unfortunate civilians. She also kills Jedite and later Zoicite, showing absolutely no remorse nor shred of willingness to relent despite Kunzite's attempt to take the blame for Zoicite's loose-cannon attempt on Tuxedo Kamen's life.
** Jedite crossed it earlier in the same season with his attempt on Tuxedo Kamen's life in his own last episode. Just as bad as Zoicite's aforementioned attempt, but what makes this one stand out is that he proceeds to taunt the Sailor Senshi about it. It's also an InUniverse example, as instead of doing as he had predicted, the Sailor Senshi promptly make their disgust known, both [[YouMonster verbally]] ''and'' [[CarFu physically]].[[spoiler: The Shitenou may not qualify however having been brainwashed by the Queen and not in real control over their actions.]]
** In the second season, Rubeus crossed it via his extremely cruel and abusive treatment of Koan, the member from the QuirkyMinibossSquad who loves him, in which he [[spoiler: first mocks her over losing to the Sailor Senshi, then gives her an explosive MacGuffin and orders her to practically ''kill herself for him''. The poor girl goes into a full-blown VillainousBreakdown at that, and only Rei's compassion and efforts keep her from commiting suicide.]] And for worse, after [[spoiler: Koan and Bertier have their {{Heel Face Turn}}s]], he goes even further than that [[spoiler:by getting their eldest sister Petz BrainwashedAndCrazy with another MacGuffin, and then leaving her and the remaining sister Calaveras to die when the MacGuffin overloads.]]

** Wiseman crosses this when he [[spoiler:corrupts the [[WellIntentionedExtremist well-meaning yet extreme goals]] of the Black Moon people and their leader Dirmando. Unlike Rubeus, Saphir [[HeelFaceTurn eventually got wise to Wiseman's act]], but Wiseman [[RedemptionEqualsDeath kills him]] just as he's about to show Dirmando the light as well. [[BerserkButton Dirmando is not amused, and it only hastens the inevitable.]]]] And then it's clinched when [[spoiler: he kidnaps Chibi-Usa when [[HeroicBSOD in a particularly low point]], then giving her FakeMemories ''and'' [[MindRape forcibly infusing her with black energy]], which turns her into Black Lady.]]
** In the third season, Telulu crosses it with how she [[AndIMustScream deals with Mimet]]. To put it in perspective, ''Sailor Moon herself'' is horrified to see one of her nemeses being dealt with in such a callous fashion. Damn... when a ''hero'' is mortified by the death of a villain (who could've killed the good guys, including him/her, with a single blow, mind you) at the hands of another villain, you know the killer in question has crossed a line.
%% Mistress 9 crossed this when ?
%% Pharaoh 90 crossed this when ?

* Nehellenia in the manga crossed this when she forcibly awakened the Sailor Quartet. And unlike her anime counterpart she was not redeemed and is evil incarnate.

TheNineties ''Manga/SailorMoon'' has a few of them:
* In the first season, for example, Queen Beryl has many acts that could easily qualify for this trope. She [[spoiler: caused the War that ended with many ruined lives and Endymion and Serenity's death and rebirth]] and years afterwards she brings Metalia into power in order to cause an Apocalypse. The way to do it is by collecting the life essence of various unfortunate civilians. She also kills Jedite and later Zoicite, showing absolutely no remorse nor shred of willingness to relent despite Kunzite's attempt to take the blame for Zoicite's loose-cannon attempt on Tuxedo Kamen's life.
* Jedite crossed it earlier in the same season with his attempt on Tuxedo Kamen's life in his own last episode. Just as bad as Zoicite's aforementioned attempt, but what makes this one stand out is that he proceeds to taunt the Sailor Senshi about it. It's also an InUniverse example, as instead of doing as he had predicted, the Sailor Senshi promptly make their disgust known, both [[YouMonster verbally]] ''and'' [[CarFu physically]].[[spoiler: The Shitenou may not qualify however having been brainwashed by the Queen and not in real control over their actions.]]
* In the second season, Rubeus crossed it via his extremely cruel and abusive treatment of Koan, the member from the QuirkyMinibossSquad who loves him, in which he [[spoiler: first mocks her over losing to the Sailor Senshi, then gives her an explosive MacGuffin and orders her to practically ''kill herself for him''. The poor girl goes into a full-blown VillainousBreakdown at that, and only Rei's compassion and efforts keep her from commiting suicide.]] And for worse, after [[spoiler: Koan and Bertier have their {{Heel Face Turn}}s]], he goes even further than that [[spoiler:by getting their eldest sister Petz BrainwashedAndCrazy with another MacGuffin, and then leaving her and the remaining sister Calaveras to die when the MacGuffin overloads.]]
* Esmeraude [[spoiler:leaves Rubeus to die on his exploding ship in Episode 74. Leaving Rubeus to die when he actually seemed to trust her would be despicable... if Rubeus hadn't done the exact same thing to the Four Sisters, which makes Esmeraude's actions more an example of KickTheSonOfABitch than anything]].
* Wiseman crosses this when he [[spoiler:corrupts the [[WellIntentionedExtremist well-meaning yet extreme goals]] of the Black Moon people and their leader Dirmando. Unlike Rubeus, Saphir [[HeelFaceTurn eventually got wise to Wiseman's act]], but Wiseman [[RedemptionEqualsDeath kills him]] just as he's about to show Dirmando the light as well. [[BerserkButton Dirmando is not amused, and it only hastens the inevitable.]]]] And then it's clinched when [[spoiler: he kidnaps Chibi-Usa when [[HeroicBSOD in a particularly low point]], then giving her FakeMemories ''and'' [[MindRape forcibly infusing her with black energy]], which turns her into Black Lady.]]
* In the third season, Telulu crosses it with how she [[AndIMustScream deals with Mimet]]. To put it in perspective, ''Sailor Moon herself'' is horrified to see one of her nemeses being dealt with in such a callous fashion. Damn... when a ''hero'' is mortified by the death of a villain (who could've killed the good guys, including him/her, with a single blow, mind you) at the hands of another villain, you know the killer in question has crossed a line.