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[[folder:Web Animation]]
* WebAnimation/{{RWBY}}: [[spoiler: [[BigBad Salem]] and her lover [[DeathIsNotPermanent Ozma]] have a long and complicated history. She's an [[CompleteMonster immortal sorceress transformed by the same dark force that creates the Grimm]], he is a [[ResurrectiveImmortality multi-incarnate wizard]] resurrected by [[AboveGoodAndEvil the Gods]] before they [[ButNowIMustGo departed Remnant]]. Their story only gets darker, sadder and weirder from there.]]
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* ''Manga/{{Devilman}}'': Akira/Ryo, the famous "gay duo" that inspired many other gay duos in later anime. Ryo is confirmed to be canonically in love with Akira, while Akira [[AmbiguouslyGay may-or-may-not]] return the feelings. And this couple is a bit zig-zagged when it comes to their position: Appearance-wise, Akira is obviously the Devil with him being the Devilman, while Ryo is the Angel for his white and gold color scheme as well as having bright white angel wings. However, personality-wise, [[DarkIsNotEvil Akira]] is the Angel for him becoming a demon to protect humanity, while [[LightIsNotGood Ryo]] is the [[FaceOfAnAngelMindOfADemon Devil]] for trying to destroy the world.

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* ''Manga/{{Devilman}}'': Akira/Ryo, the famous "gay duo" that inspired many other gay duos in later anime. Ryo is confirmed to be canonically in love with Akira, while Akira. [[note]]Ryo rarely ever confesses his love to Akira [[AmbiguouslyGay may-or-may-not]] return directly, in most adaptions. Showing how adverse to sentimentality he is, he typically tells other people long before Akira finds out.[[/note]] Akira on the feelings.other hand is [[LoveTriangle in love with Miki,]] but has shown the occasional moment of odd affection for Ryo that suggests there's something there. And this couple is a bit zig-zagged when it comes to their position: Appearance-wise, Akira is obviously the Devil with him being the Devilman, while Ryo is the Angel for his white and gold color scheme as well as having bright white angel wings. However, personality-wise, [[DarkIsNotEvil Akira]] is the Angel for him becoming a demon to protect humanity, while [[LightIsNotGood Ryo]] is the [[FaceOfAnAngelMindOfADemon Devil]] for trying to destroy the world.

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** A very popular ship in ''Anime/YuGiOhArcV'' is Zarc and Ray due to the fact 3 out of 4 of their reincarnations having in-universe ShipTease. Zarc is described in-universe with terms like demon and devil and desired to destroy all reality. Ray is his opposite and protects the world instead, she is usually shown in golden light and was ultimately the person that saved reality twice thus acting as the angel or god to his demon or devil.


* ''Anime/NeonGenesisEvangelion'': Plenty of Shinji/Asuka fanfiction portray them as having this type of relationship. In canon, they're attracted to each other; Asuka sometimes flirts aggressively with the very shy Shinji and Shinji ultimately ends up [[spoiler:both masturbating to Asuka's comatose body and strangling her]].


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[[folder: Comic Books]]
* ComicBook/TheJoker is AxCrazy and unpredictable to the extreme and as such it's difficult to pin down his motivation, past, and the like in canon. What is more clear cut is his demented love and obsession with Franchise/{{Batman}}. It seems his greatest desire is to break Batsy's ideals down and make him just like him. Batman isn't the type to let Joker victimize him but in certain fanworks Batman is made vulnerable and at the Jokers mercy.

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[[folder: Comic [[folder:Comic Books]]
* ComicBook/TheJoker is AxCrazy and unpredictable to the extreme and as such it's difficult to pin down his motivation, past, and the like in canon. What is more clear cut is his demented love and obsession with Franchise/{{Batman}}. It seems his greatest desire is to break Batsy's ideals down and make him just like him. Batman isn't the type to let Joker victimize him but in certain fanworks fan works Batman is made vulnerable and at the Jokers mercy.



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[[folder: Web Animation]]
* ''WebAnimation/{{Happy Tree Friends}}'': Flaky and Flippy, especially when fan flanderization comes into play. Flippy ''is'' normally a nice fellow, but he is more well-known for his extremely violent SplitPersonality that [[TraumaButton gets triggered]] ''very'' easily. Flaky in contrast is a cute ShrinkingViolet and his closest friend.

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[[folder: Web [[folder:Web Animation]]
* ''WebAnimation/{{Happy Tree Friends}}'': ''WebAnimation/HappyTreeFriends'': Flaky and Flippy, especially when fan flanderization comes into play. Flippy ''is'' normally a nice fellow, but he is more well-known for his extremely violent SplitPersonality that [[TraumaButton gets triggered]] ''very'' easily. Flaky in contrast is a cute ShrinkingViolet and his closest friend.



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* Downplayed example: Bakugou Katsuki from ''Manga/MyHeroAcademia'' is not straight up ''evil'', but he is a rather vicious and ruthless bully and a major BloodKnight, an AntiHero bordering on SociopathicHero. Naturally, this has prompted fans to ship him with his childhood bullying victim [[TheHero Izuku Midoriya]], with [[NiceGirl Uraraka Ochako]] being another popular option. Neither of these are as common as shipping Bakugou with [[BoisterousBruiser Eijirou Kirishima]], though this at least works better as Bakugou [[PetTheDog generally acts nicer to him than the previously mentioned two]].



* ''WebAnimation/{{Eddsworld}}'': Cute {{Adorkable}} NiceGuy Edd is frequently paired with TriggerHappy ChummyCommie Tord. Not hurt at all by the fact that Edd is depicted in-universe as Tord's MoralityPet. Less common but still there is pairing [[TheDitz Matt]] with Tord. The ''most'' popular ship in the fanbase, Tom/Tord doesn't qualify as Tom is depicted as being [[TheCynic as far from an angel as you can get]].

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* ''WebAnimation/{{Eddsworld}}'': Cute {{Adorkable}} NiceGuy Edd is frequently paired with TriggerHappy ChummyCommie [[ChummyCommies chummy communist]] Tord. Not hurt at all by the fact that Edd is depicted in-universe as Tord's MoralityPet. Less common but still there is pairing [[TheDitz Matt]] with Tord. The ''most'' popular ship in the fanbase, Tom/Tord doesn't qualify as Tom is depicted as being [[TheCynic as far from an angel as you can get]].

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* ''WebAnimation/{{Eddsworld}}'': Cute {{Adorkable}} NiceGuy Edd is frequently paired with TriggerHappy ChummyCommie Tord. Not hurt at all by the fact that Edd is depicted in-universe as Tord's MoralityPet. Less common but still there is pairing [[TheDitz Matt]] with Tord. The ''most'' popular ship in the fanbase, Tom/Tord doesn't qualify as Tom is depicted as being [[TheCynic as far from an angel as you can get]].


* ''WesternAnimation/AngelsFriends'': The main couple, Raf and Sulfus, are literally angel and demon.

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* ''WesternAnimation/AngelsFriends'': The main couple, Raf and Sulfus, are literally angel and demon. While Raf is an optimistic, compassionate, and strong-willed, Sulfus is a JerkWithAHeartOfGold who is arrogant and pessimistic.


* ''Franchise/SonicTheHedgehog'':

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* ''Franchise/SonicTheHedgehog'': ''VideoGame/SonicTheHedgehog'':



* ''Franchise/SonicTheHedgehog'': Rouge and Knuckles aren't a couple but they get a lot of ShipTease. Their relationship sways between this and DatingCatwoman depending on [[DependingOnTheWriter how heroic Rouge is portrayed]]. At minimum, she's a coy thief that contrasts with Knuckles' straight-laced heroism.

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* ''Franchise/SonicTheHedgehog'': ''VideoGame/SonicTheHedgehog'': Rouge and Knuckles aren't a couple but they get a lot of ShipTease. Their relationship sways between this and DatingCatwoman depending on [[DependingOnTheWriter how heroic Rouge is portrayed]]. At minimum, she's a coy thief that contrasts with Knuckles' straight-laced heroism.

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* ''Franchise/SonicTheHedgehog'':
** Maria was Shadow's MoralityPet and his OnlyFriend in the past. Shadow would be a villain instead of an anti-hero if not for Maria's kind personality and dying wish to him.
** Shadow/Amy comes down to this. Amy reminds Shadow of Maria, which is a major factor in his [[spoiler:HeelFaceTurn]]. Amy is loving and energetic while Shadow is cold and dark.
** Sonic's nice StockShonenHero blends with Shadow's stoic StockShonenRival to make the two a popular ship.
** The popularity of Shadow and Tikal together comes down to their clashing personalities. Shadow is a dark, brooding character while Tikal is a caring martyr who died centuries (if not, millenia) ago.
** Rookie/Infinite from ''VideoGame/SonicForces'' is popular despite Rookie being a wide-eyed KidHero while Infinite is a mind-screwy murderer who loathes the protagonist.


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* ''Franchise/SonicTheHedgehog'': Rouge and Knuckles aren't a couple but they get a lot of ShipTease. Their relationship sways between this and DatingCatwoman depending on [[DependingOnTheWriter how heroic Rouge is portrayed]]. At minimum, she's a coy thief that contrasts with Knuckles' straight-laced heroism.


* ''[[https://nomnomnami.itch.io/contract-demon Contract Demon]]'' has an angel and the demon she formed a contract with fall in love. Humorously, the angel is the one who's rather eager for this kind of relationship whereas the demon is far more awkward and hesitant about matters of romance/sex (and isn't even very good about the whole DealWithTheDevil thing because she's just too nice to actually want to tempt/hurt her "victim"). [[spoiler:Also, the "angel" is actually a human witch who pretended to be an angel because she ''really'' wanted to roleplay this trope.]]

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* ''[[https://nomnomnami.itch.io/contract-demon Contract Demon]]'' has an angel and the demon she formed a contract with fall in love. Humorously, the angel is the one who's rather eager for this kind of relationship whereas the demon is far more awkward and hesitant about matters of romance/sex (and isn't even very good about the whole DealWithTheDevil thing because she's just too nice to actually want to tempt/hurt her "victim"). [[spoiler:Also, the "angel" is actually a human witch who pretended to be an angel because she ''really'' wanted to roleplay this trope.]]

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* ''[[https://nomnomnami.itch.io/contract-demon Contract Demon]]'' has an angel and the demon she formed a contract with fall in love. Humorously, the angel is the one who's rather eager for this kind of relationship whereas the demon is far more awkward and hesitant about matters of romance/sex (and isn't even very good about the whole DealWithTheDevil thing because she's just too nice to actually want to tempt/hurt her "victim"). [[spoiler:Also, the "angel" is actually a human witch who pretended to be an angel because she ''really'' wanted to roleplay this trope.]]


* ''WesternAnimation/KimPossible'' has the hugely popular [[HoYay/WesternAnimation Les Yay]] pairing of Kim/Shego.

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* ''WesternAnimation/KimPossible'' has the hugely popular [[HoYay/WesternAnimation Les Yay]] pairing of Kim/Shego.

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* ''WesternAnimation/TheCrumpets'': Marylin and Caprice are a goth teen couple. While both are protagonists, Caprice is rude and hates animals at heart. Marylin is kind and loves animals so much they capture most of his attention during their first date.


* ''WesternAnimation/AngelsFriends'': Raf and Sulfus.

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