History SissyVillain / AnimeAndManga

** Frieza is a petite, painstakingly polite alien with a color scheme of pink, purple, and white who happens to be a {{sadist}}ic, {{sociopath}}ic GalacticConqueror. He is voiced by a woman with [[EvilSoundsRaspy a raspy old lady voice]] in the English dub[[note]]Specifically the Creator/{{Funimation}} and [[Creator/TheOceanGroup Ocean]] dubs with Creator/LindaYoung and Pauline Newstone respectively[[/note]] and complains about not wanting to break his nails during his fight with Goku. However, in the original Japanese [[VocalDissonance he has a]] [[EvilSoundsDeep deep voice]] and a masculine way of speaking. Frieza's newest VA, Creator/ChrisAyres, has a raspy, high-pitched though still noticeably masculine voice similar to the voice Creator/LittleKuriboh gives him.

* Masao from ''Manga/{{Shiki}}'' may qualify, as he's wimpy and somewhat effeminate-looking (though any actual feminine traits he has tend to be somewhat downplayed). Interestingly enough, he appears to be straight while Natsuno, who's one of the few heroic characters in the story, is often considered AmbiguouslyGay.

* Johan Liebert, the titular ''Anime/{{Monster}}''. [[spoiler:He crossdresses, but it's because he sees himself and the sister he's dressing as as essentially the same person, with no definition between them. And he's too damaged and empty to even qualify as UsefulNotes/{{asexual|ity}} in the healthy orientation sense, let alone gay.]]

* Harley from [[Anime/PokemonTheSeriesRubyAndSapphire the Hoenn saga]] of ''Anime/PokemonTheSeries'' embodies this trope to the fullest. He's one of the most cold-hearted rival characters in the show and he [[KickTheDog treats May like crap]], but he always looks fabulous doing it, with long purple hair and a [[BareYourMidriff navel-baring]] outfit themed based on his [[SignatureMon Cacturne]]. He even [[CreepyCrossdresser wore May's outfit out of spite one time...]] and he [[https://i.ytimg.com/vi/KzMOnFuClLY/maxresdefault.jpg fit the look pretty darn well]]! He certainly is "Everyone's favorite naughty coordinator".

** James of [[GoldfishPoopGang Team Rocket]] is perhaps a less gratuitously obvious case than Harley, but he still certainly fits the bill and acts as the most prevalent example throughout the entire show. He's a violet-haired Bishonen and consistently the gentlest [[ExtremeDoormat and the butt]] of the TerribleTrio, has a CutenessProximity that often leads him to raising [[RidiculouslyCuteCritter adorable Pokémon]] like Cacnea, Mime Jr. and Inkay, has a ''long'' history of villainous crossdressing disguises [[WholesomeCrossdresser which frequently convince others and have even earned compliments]], and has the campest and least aggressive demeanor of the trio by far - this has typically [[MasculineGirlFeminineBoy put him at contrast with the more assertive and temperamental Jessie]]. That being said, while a certified ButtMonkey by profession, these 'sissy' qualities are mainly positive ones: James is [[OnlySaneMan definitely the most morally conscious of Team Rocket]] and thus likeliest to object to their plans, and his [[OverprotectiveDad doting and maternal nature]] towards Pokémon has consistently acted as a redeeming quality, and he's usually a downright NiceGuy when he isn't trying to steal anything.

* Harley from ''Anime/PokemonTheSeries'' embodies this trope to the fullest. He's one of the most cold-hearted rival characters in the show and he [[KickTheDog treats May like crap]], but he always looks fabulous doing it. He's "Everyone's favorite naughty coordinator."

** The English dub gives Rohan Kishibe a stereotypically effeminate voice.
* Gender inverted with Nui Harime from ''Anime/KillLaKill''. She's one of [[BigBad Ragyo's]] CoDragons, as well as a {{giggling|villain}} GirlyBruiser with her bow, earrings, [[KickingAssInAllHerFinery frilly]] MinidressOfPower, forearm pads, boots, and ParasolOfPain all in {{pink|MeansFeminine}} and white.

* ''Manga/DragonBall'':
** Frieza. A petite, painstakingly polite alien with a color scheme of pink, purple, and white who happens to be a {{sadist}}ic, {{sociopath}}ic GalacticConqueror. He is voiced by a woman with [[EvilSoundsRaspy a raspy old lady voice]] in the English dub[[note]]Specifically the Creator/{{Funimation}} and [[Creator/TheOceanGroup Ocean]] dubs with Creator/LindaYoung and Pauline Newstone respectively[[/note]] and complains about not wanting to break his nails during his fight with Goku. However, in the original Japanese [[VocalDissonance he has a]] [[EvilSoundsDeep deep voice]] and a masculine way of speaking. Frieza's newest VA, Creator/ChrisAyres, has a raspy, high-pitched though still noticeably masculine voice similar to the voice Creator/LittleKuriboh gives him.
** Zarbon until he changes into his [[PowerUpgradingDeformation final form]]. Particularly in the redub with his voice, which sounds like a cross between King Cold and Caroni.
** The ''Creator/TeamFourStar'' [[TheAbridgedSeries abridged series]] plays up Zarbon’s campness to the point where he speaks almost entirely in {{double entendre}}s [[spoiler: - but it was subverted in episode 17 when it was revealed that he is in fact [[CampStraight straight]], and is shocked to find out that everyone around him thinks he's gay]].
** Further back than that, there is [[CampGay General Blue]] of the Red Ribbon Army. A ruthless, homicidal goose-stepper who is irked with having to dive into grimy-looking water, is disgusted by Bulma's advances on him and [[EekAMouse freaks out when he sees a rat passing by]][[spoiler:, which ends up saving Goku and his friends' lives as this freakout causes him to lose focus of his paralysis technique and release Goku from it]].

* Hiromi Kisiragi of ''Manga/{{Eyeshield 21}}'' is cornerback for the [[OpposingSportsTeam Hakushuu Dinosaurs]], CoDragons to ManipulativeBastard Marco alongside [[TheJuggernaut Gaou]], and an incredibly [[UnnecessaryRoughness cruel player]] who tries his best to dislocate the arms of receivers. He's also a mincing pretty-boy with a massive mancrush on Gaou and the belief that [[TheFightingNarcissist strength is a true indicator of beauty]]. It's actually justified in his case and played sympathetically--sick of being bullied due to his effeminate nature and looks he joined the football team to get a life and was turned into the PsychoSupporter he is today by Marco.
* Yuda from ''Manga/FistOfTheNorthStar''. While his large harem seems to imply he's straight, he's nonetheless obsessed with his own physical perfection, to the point of being worried about scars in battle. This makes him look even more cowardly and twisted. In one of the most "manly" Manga/anime series, the master of [[FantasticFightingStyle Red Crane Nanto]] is obviously depicted as everything a proud warrior should not be. Moreover he weirdly shows his "admiration" for Rei and uses a very heavy make-up,but he's still a fighter, so he's quite muscular, as anyone there besides casual oppressed peasants/children.
* ''Manga/FullmetalAlchemist'': [[SevenDeadlySins Envy]] has an extremely androgynous appearance, coupled with an [[CreepyCrossdresser effeminate outfit]] and whiny voice. However, he is a ruthless, murderous nutcase who goes out of his way to cause as much suffering as he can.
** Envy is something of an unusual case, as ''they'' technically don't have a gender, with the ([[VoluntaryShapeshifting default]]) form they choose to take being somewhere between female and male. It should, however, be worth noting that most characters through the series refer to Envy using male pronouns, though this is because in the English language, "He" is the gender-neutral pronoun someone is supposed to say when the gender is unknown.
** This is only the case in the manga and Brotherhood anime. In the 2003 anime, Envy is definitely male [[spoiler:and Ed's older brother]].

** From Mereum's Royal Guard, there's Shiapouf. There's no ViewerGenderConfusion like there is with [[CatGirl Pitou]], but his personality is much more fey and dramatic on top of being a butterfly-humanoid chimera ant.

* ''Manga/InuYasha'':

* Two ''Anime/SpeedGrapher'' villains qualify. Shirogane, the RubberMan euphoric, is a very arrogant and somewhat campy ballet instructor who in his transformed state, runs around in what looks like a gimp suit. More sympathetically is Tsujido, the leader of the TerribleTrio, who wears something that could pass for a SpyCatsuit with his AbsoluteCleavage jacket unzipped half-way. Whether or not his feelings for his boss, [[TheDragon Suitengu]], run any deeper is ambiguous, but it was [[WordOfGod clearly stated]] he was supposed to "give off an atmosphere of having an AmbiguousGender".

* Kano in ''Anime/{{Texhnolyze}}'' is effeminate and physically unimpressive, as well as a schizophrenic soplisist [[IncestIsRelative produced from generations of selective inbreeding]].

** Mukuro was this before his ambiguous HeelFaceTurn. The guy picked Kokuyou Junior High because of ''how stylish the uniforms were''. His sexuality is quite ambiguous as well, considering how much FoeYay he has with Hibari and Tsuna in particular. His plans of taking over Tsuna's body so he could get revenge on the mafia also carried some questionable subtext, what with all his talk of "wanting Tsuna's body", telling Tsuna to "give me your body", and that "with my technique you will soon be mine."

** [[spoiler:[[WildCard Furuta]] [[FinalBoss Nimura]]]] is CampStraight (though he does have the occasional FoeYay with Kaneki) and in love with [[FemmeFatale Rize]], and many fans describe him as fabulous and fruity (it's a pun on his name). He certainly is conventionally sexy, with a gothic appearance, and dresses smartly while mincing around and posing in suggestive and [[{{Narm}} comical]] fashions.

** Neferpitou, a (maybe) male cat-humanoid chimera ant with a very feminine appearance and mannerisms.
** Also from Mereum's Royal Guard, there's Shiapouf. There's no ViewerGenderConfusion like there is with Pitou, but his personality is much more fey and dramatic on top of being a butterfly-humanoid chimera ant.