Sissy Gay Boy ((INSTALL))
Frequently, The Hero pitted against the Sissy Villain is either a manly man (any feminine traits he has are merely there to underscore his masculinity) or a tomboy, and making the villain "unmasculine" is intended to emphasize this. After all, there's nothing manlier than beating up a sissy. It doesn't even matter that the limp-wristed villain is powerful, he looks weak and homosexual and that's what matters.
sissy gay boy
Literature The Pardoner from The Canterbury Tales. He's a rather effeminate guy, and there's a scene where the Host, a Boisterous Bruiser makes a threat which could be loosely paraphrased as "I'd cut off your balls if you had any."
Valentine Wolfe, evil space aristocrat junkie extraordinaire, from the Deathstalker books. He's more outrageously decadent than feminine, but he does wear makeup and have a rather camp way of expressing himself at times, while remaining an absolute unholy terror in the highest echelons of the Decadent Court. Vicar Kassar: You look like a degenerate. Wipe that paint off your face. Valentine: Lick it off.
The villain of German novel Der Eiskristall is an unusual variation - it is implied that he turned to evil partly because he was bullied about his feminine looks. While he is trying to assert his masculinity with extreme violence, he is not helping his case with the Ho Yay he has with one of the male protagonists.
Mad Scientist and Big Bad Nirai Kujen in The Machineries of Empire is very pretty, loves his frills, sometimes behaves in a camp manner, and is bisexual. He's also a sadistic psychopath with a body count in the billions, if you count direct and indirect results. Doesn't have the common homophobic implications of the trope as the setting is an Everyone Is Bi Free-Love Future.
In the self-titled first book in the prose Modesty Blaise series, female Psycho for Hire Mrs. Fothergill is a distaff counterpart, as she is depicted with a lot of Butch Lesbian signifiers but is never explicitly described as such. (She seems to be more into killing people than sex of any kind.)
Emperor Ublaz Mad Eyes of Redwall. His evil plan, which results in the slaughter and misery of hundreds of creatures by his followers, is to get hold of the Artifact of Death. The Artifact Of Death consists of six pink pearls which he wants to wear in a crown. They don't even have any magical powers (except for bringing horrible luck on everyone who owns them, but he apparently doesn't know that), he just wants a pink pearl crown. Yeah.... He also wears silk robes and perfume and paints his nails.
Lord Pumphrey, a.k.a "Pumps" in Sharpe. Variously known as "the molly," "that woman," and believed to have a crush on the hero. He is also one of the most effective Manipulative Bastards in the series, even mocking Sharpe to his face when confronted. He is, thus far, a well-earned Karma Houdini.
Zhong Ye, the eunuch sorcerer Big Bad in the young adult novel The Silver Phoenix: Beyond The Kingdom of Xia. However, while he is dandified and creepy, he's portrayed as a depraved heterosexual - and the heroine is the reincarnation of his lost love.
Mr. Jones in Joseph Conrad 's Victory is the murderous, amoral ringleader of a group of bandits, and is described as a foppish, homosexual dandy. In spite of (or perhaps because of) his effeminacy, he also hates women and doesn't tolerate their presence.
A Song of Ice and Fire: The eunuch Lord Varys looks like this trope to an absolute T - he wears fancy robes in non-militaristic styles, indulges in fine perfumes of exceedingly good taste, powders and shaves a lot, swishes quite primly and silently, expresses bemused understanding of other peoples' sexual foibles (while pointing out his lack of same with no subtlety whatsoever) and has a habit of giggling and snarking at both opportune and inopportune moments. And then subverts this trope, being a Master of Disguise and a Master Actor, playing up the "sissy" aspect because that's what people expect to see - behind the perfume and giggles he's a Determinator who isn't afraid to get all up in the hero's grill. Possibly the top Chessmaster in a series notorious for its Gambit Pileup.
The downplayed Petyr "Littlefinger" Baelish. In a nation where the ruling class follows a strictly martial lifestyle, Littlefinger is overtly all brains and no brawn. He has a small stature and an immaculately groomed appearance, and he chews mint so his breath is always fresh. He earned his place at court with his head for accounting and exists as a Sleazy Politician, always quick with a quip. He's also a Chessmaster and Devil in Plain Sight whom everyone seems to agree is up to some scheme or another.
From Tales of Dunk and Egg we get Daemon Blackfyre II. On paper, he's this trope: heads a rebellion that would see Egg and his side of the family dead if it succeeds, has a very Transparent Closet, enjoys dressing up in an overly rich "disguise" a smidge too much and is about as accomplished martially as your average bag of marshmallows. But... he's not much of a villain (malicious and cruel he isn't; somewhat boorish is the most he manages) and he is definitely no mastermind. Those would be his "followers" using him. He pays the price for playing the Game, regardless.
Professional Wrestling The effeminate heel, Gorgeous George, is an archetype in wrestling. Didn't actually start with George Wagner, but he is one of the most imitated.
"Exotic" Adrian Street, the most imitated Gorgeous George, more so than the original Gorgeous George himself. Despite acting like a sissy, he would talk himself up like he was the toughest thing ever.
On the managerial side of things we have Jim Cornette, best known for cowering with The Midnight Express and crying about his mother up until a video of him getting out of his car to yell at a Dairy Queen worker who did not bring him the meal he ordered started circulating amongst wrestling fans, turning him into a memetic badass.
Adrian Adonis' gimmick went from tough biker to flamboyant, effeminate gay. Actually, flamboyant is an understatement. In reality, Adonis was given the gay "Adorable Adrian" gimmick as a punishment after he failed to act on Vince McMahon's request to lose weight (Adonis was pudgy, and Vince has a well-documented preference for chiseled, muscular physiques). No one expected Adonis to embrace the gimmick the way he did. He even kept it after he left the WWF in 1987.
Rick "The Model" Martel, who incidentally feuded with an ambiguously gay but not sissy Shawn Michaels.
Subversions: Big Dick Johnson is kind of a sissy, but he's never portrayed as villainous; Goldust is pretty effeminate, but he's definitely not a sissy.
Lacey, a straight woman, later described the early advances of her eventual boyfriend Jimmy Jacobs as being "gay". Jacobs had always been something of a dork but at some point he decided he was "tough", so tough he no longer had to do anything considered "tough" and would in fact go out of his way to do the opposite of tough, such as stripping down and cuddling with a picture of his future girlfriend while singing her praises. Jacobs was such an example it made the Jerk Jock Colt Cabana (who the fans were happy to see Homicide attempt to murder) into a baby face just for opposing him.
"Dashing" Cody Rhodes, before he Took a Level in Badass. He gave grooming tips and his Berserk Button was being hit in the face.
Tyler Breeze, who's billed from a different location depending on the season. His Titantron is a live feed of his phone's camera taking selfies.
Radio Mr. Gently Benevolent in Bleak Expectations epitomises and parodies this trope whilst being Ambiguously Gay.
Theater King Herod is often portrayed this way in Jesus Christ Superstar.
Don Dorcha from Lord of the Dance is a subversion. You'd expect a villain who only expresses himself through dance to have at least a shade of sissy, but Don Dorcha and his army are never anything less than foreboding and menacing.
Farquaad is played up as this in Shrek: The Musical.
Herbert from Tanz Der Vampire. While the degree of his villainy is debatable and highly dependent on the actor, Herbert still remains a clingy, aggressive and bloodthirsty vampire. A VERY flamboyant bloodthirsty vampire. He's also the responsible for Alfred's nightmare during the "Carpe Noctem" dance sequence.
A Very Potter Musical: Lord Voldemort is a Neat Freak who can't sleep knowing there are clothes just lying around in his bedroom, and a fan of romantic comedies like She's All That.
Professor Quirrell is even more of one, to the point that even Voldemort calls him a sissy.
Gender Inverted in the sequel, where Dolores Umbridge is the epitome of macho. Dumbledore even mistakes her for a man initially.
Visual Novels From Ace Attorney: Richard Wellington is a mean of wealth, taste and art. He himself is a great con artist. Oh, and a murderer, of course.
Subverted with Jean Armstrong. He's sissy all right, but not evil, just desperate because of how deep in debt he is.
Kristoph Gavin pays a lot of attention to his looks, and even wears nail polish. That doesn't stop him from being downright terrifying.
FINALLY, Florent L'Belle would LIKE to point out that the only VILLAINS here are those UNABLE to comprehend his MAGNIFICENT beauty.
Miguel Kurashiki in Rose Guns Days fits the trope to a T, with a strong emphasis on the mysogynistic part. He also has a close relationship and plenty of Ho Yay moments with his boss Caleb. Season 2 gives him a good deal of Character Development though.
Togainu no Chi: Arbitro swishes about in a feather boa, has a cleanliness fetish, collects statues of pretty boys....