Kyle: "How did you finally come to terms with it? The gay thing?"
The Annihilator: "I became the most powerful and feared supervillain on the planet. After that 'the gay thing' really didn't seem to matter so much"A homosexual member of organized crime. This is particularly common in British works set around the 1950s and 60s, as the notorious 1960s London Gangster Ronnie Kray was fairly openly bisexual. Many fictional Gayngsters are No Celebrities Were Harmed fictionalised versions of him, to some degree. In the US, the Gayngster is often a Scary Black Man or Latino. The character can be repressed or fairly open about it, but an important idea is the contrast between his "un-masculine" (how he would see it) sexual orientation and brutal, macho behavior. Not related to Gayngst, but overlap is possible. May overlap with Armoured Closet Gay, Manly Gay and Badass Gay.
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Anime & Manga
- A lot of members from the mafia in Katekyo Hitman Reborn! have extremely questionable sexuality... but for a more obvious, straight-forward example, Lussuria from the Varia is shown outright to be gay.
- Gauron from Full Metal Panic! could count, though he's more towards the side of being a terrorist than a gangster. However, he does do shady dealings with smuggling in the underground world, and generally acts like one. His brutal, macho behavior is definitely a contrast to his twisted and obsessive love for Sousuke, making him a pretty good example of being a Straight Gay.
- There are plenty of yakuza characters in yaoi anime and manga. For a start, Masa and Kai from Kizuna, Ranmaru from Ikoku Irokoi Romantan and Asami in Yamane Ayano's Finder Series.
- Not to mention the shoujo classic Banana Fish.
- Tokyo Tribes: One of the mob bosses is a Fat Bastard who rapes boys so hard they explode. Really.
- Tsukuyomi in Mahou Sensei Negima! is basically a terrorist (as far as Sayo is concerned). She's also an extreme Psycho Lesbian.
- Minor villains Squalo and Tizziano from the fifth arc of Jo Jos Bizarre Adventure; and a couple dedicated enough that Tizziano doesn't hesitate to intercept a salvo from Aerosmith meant for Squalo. Everyone else, including the protagonists, comes off as almost Camp Gay due to their really weird clothes, but don't really show any attraction to the same sex. Or the opposite sex, for the most part.
- The great Mr. 2 Bon Clay from One Piece.
- The leader of the G Boys in the manga of Ikebukuro West Gate Park is all but explicitly said to be gay. None of his underlings are though.
- Paranoia Agent features a yakuza boss who's into younger men.
- Jin Lee and Yeong Joon in the Korean manhwa "Kill Me Kiss Me" are both part of the Yi Won gang, and romantically involved with each other. The only reason Ghoon-Hahm (the gang leader) doesn't "beat Jin Lee staight," is because Jin is the gang's money man.
- In Narutaru, a gang of thugs calls in a gay gangster for the sole purpose of raping the Wholesome Crossdresser who just gives an Unsettling Genderreveal before they kill the crossdresser.
- Arguably, Mello from Death Note, if you believe the fangirls.
- Remember Jakotsu of the Band of Seven? An extremely creepy Depraved Gayngster Yandere.
- In one episode of Cowboy Bebop, the crew burst in on a low-rank gang member in mid-coitus with his boyfriend in order to interrogate him about the whereabouts of his boss.
- Tsujido of Speed Grapher is implied to be gay and have a romantic quality in his devotion to his boss Suitengu. He and the other members of the Terrible Trio were implied to be involved in petty crime prior to being rescued by Suitengu in their backstory, and they are certainly gangsters during the series.
- Jun Sekiya, the leader of the Toujou-gumi, in Wild Adapter is explicitly gay. Sanada, leader of the Izumokai, may be; he shows an interest in Kubota, but it isn't clear if he usually likes men or if its just Kubota.
- The second volume of One Hundred Bullets features the obese, effeminate and openly gay Baby Maxwell in Detroit.
- Former Minuteman and all around tough guy Mr. Shepherd was implied to be gay in a flashback to his youth.
- Ultimate X-Men's Colossus was a Russian Mob enforcer and heavily closeted gay and mutant for years in his Back Story.
- Gilbert Hernandez's "Poison River" story in Love and Rockets features several Gayngsters.
- In one of DC's Milestone Comics "Blood Syndicate", Fade is a perfect example of this. Fade is deeply closeted and in love with the leader of the Syndicate Tech 9, who he even tries to confess to before Tech dies.
- Phat from X-Statix isn't a real gangbanger, but he deliberately spread the lie that he is as a "hook" to get him on the team. He starts a Faux Yay relationship with teammate Vivisector when they think they're being left out of the spotlight, and eventually both realize they really are gay.
- One story of Nikolai Dante included a homosexual Expy of both Ramone and Finnigan. Very much the Camp Gay vibe, to go with the deadly.
- The Big Bad in Ringo Lam's Full Contact, starring Chow Yun Fat.
- Gayngsters were an integral part of the Film Noir trope, right from the 1941 adaptation of The Maltese Falcon to 1955's The Big Combo.
- The Rock played one of these in Be Cool.
- Kirill in Eastern Promises. It's highly taboo in the Russian mob, so he has someone killed just for insinuating that one of the Russian mobsters was gay. He's got a really big thing for his right-hand man, played by Viggo Mortensen.
- Played for Laughs in The Italian Job (1969) with Camp Freddy. In fact, dressing/acting camp was kind of a Gang of Hats for his group, and it should be remembered that the Boss (famously operating from a Luxury Prison Suite) was played by NoŽl Coward.
- Layer Cake describes one from the 1970s nicknamed "Crazy Larry" who memorably commented "fucking females is for poofs". The main character is also accused of being one of these by his boss, given that he is much less macho than other gangsters (considering himself just a businessman). Punning on the predilection of this character-type for "rent boys", the boss invents the Unusual Euphemism of asking him if he is "behind with the rent".
- Harry Stark of The Long Firm.
- Bernie Bernbaum and Eddie Dane from Millers Crossing.
- The Punisher (2004) had Quintain Glass, Howard Saint's best friend and second in command as a closet gay... at least from him. His wife apparently knew. This came to a head when Frank blackmails him with outing him, and uses that and other forged/out of context evidence to implicate him and the mobsters wife as having an affair! The boss ends up killing his friend and wife, but not after slapping her for "insulting" his memory by claiming he was gay just to save her own skin.
- Hilly Blue (Divine) is the leader of the crime syndicate in Trouble in Mind, slightly Subverted by the fact that he's in the Transparent Closet.
- Lucky Number Slevin featured the character called "The Fairy,'' the gay son of another gangster called "The Rabbi."
- "The Gangster" from Gangster No. 1 is hinted at being a latent homosexual due to his misogyny and fixation on glamorous crime prince Freddie Mays.
- Sappensly and Quill, the two white bounty hunters from Bring Me the Head of Alfredo Garcia: Though not overt, the two are joined at the hip, react with disgust at the advances of two prostitutes, and Sappensly loses his shit after Quill dies. Quill is also a notably phallic name.
- Japanese director Takashi Miike is fond of this trope. Examples:
- Handsome Bob from Rock N Rolla provides one of the more hilarious scenes of the movie when he comes out to his co-worker One Two. Turns out One Two was the only person who didn't know, and also the only one who had a hard time accepting it. For everyone else, the fact that Bob is awesome overrode the fact that Bob was gay.
Mumbles: I'll tell you something, Mister One Two. If I could be half the human that Bob is at the price of being a poof, I'd think about it. [beat] Not for too long, but I'd have to pause, y'know?
- If it wasn't for Bob's quick thinking in Lennie's hideout, the whole Wild Bunch, Johnny and possibly Archy would be dead. He puts two-and-two together when Johnny mentions Lennie "grassing Archy up", to realize A: that "Sidney Shaw" is Lenny, and B: that Archy must know about "Sidney".
- In Victor/Victoria Julie Andrews plays a woman pretending to be a male drag queen who catches the eye of gangster "King" Marchand. who is conflicted because he thinks she's a man. Meanwhile, King's bodyguard Squash actually is gay and has a fling with Victoria's Mentor Toddy. King is almost forced out of the business because another gangster thinks he's gay and in Toddy's words, "You can kill a man but not kiss him."
- Vinnie from Stonewall.
- Teddy Bass, "Mr. Black Magic" himself, from Sexy Beast. Teddy attends Roman-style orgies to meet wealthy and powerful men and steal from them.
- Meredith from 44 Inch Chest is another great Ian McShane Gayngster moment.
- Friends and Family makes this trope the main movie theme. The main characters are an open, loving couple of handsome mafia bosses. The twist appears when their families come for a surprise visit. This is a subversion of the classic Coming-Out Story, as their parents know they're engaged, but they don't know they're gangsters.
- The James Bond movie Diamonds Are Forever gives us Mr. Wint and Mr. Kidd, vicious killers who are never apart and hold hands while walking away from helicopter explosions. Once, Mr. Wint compliments one of their female targets, and gets a glare from Mr. Kidd before adding "...for a lady,". Mr. Kidd remains unimpressed.
- Chris Penn's character in Corky Romano, though he denies it for most of the film.
- Carlos in Quinceanera.
- Ricki from Gigli. A lesbian gangster, for a change.
- Ivan and Orlando, a couple of Manly Gay henchmen from Perrier's Bounty.
- Yamada in Sharkskin Man And Peach Hip Girl. He falls in love with his target.
- Harry Flowers, The Don, in Performance, is hinted to be gay several times and finally shown to share a bedroom with one of his subordinates. The main character, Chas, is homophobic and in deep denial about his boss.
- Leonard, Martin Landau's character (according to Word of Gay) in North By Northwest.
- Kerrigan in High Heels And Low Lifes (according to his subordinate, Mason, who refers to him as "the old pouf".
- Frankie Flowers, the Assassin working for The Cartel in Traffic. A cop with exclusive knowledge of this uses it to catch him at a gay bar, pretending to proposition him for sex.
- There's also a bisexual/lesbian couple of hitmen in Smokin' Aces. Vague hints of Gayngst as well.
- James Gandolfini's character in The Mexican is a professional hitman/badass.
- The subtext of Little Caesar is that Edward G. Robinson has a crush on Douglas Fairbanks.
- Tha Argentine film Plata Quema (Burnt Money) is the story of El Nene and Angel, a gangster couple referred to as "the twins". Based on a real robbery in Argentina in 1965.
- Don Bruce from Myth Adventures, the Mob's "fairy Godfather." Not confirmed until we start getting books from Guido's viewpoint, but he's Camp Gay even in the Skeeve books.
- Eric Flint's Timestrike has an openly gay ex-hit man as one of its main characters.
- Gino Fish in Robert B Parker's Spenser, Sunny Randall and Jesse Stone novels.
- Harry Stark in Jake Arnott's The Long Firm is intentionally something of an No Celebrities Were Harmed version of Ronnie Kray.
- Turning this trope Up to Eleven, in Neil Gaiman's story "Keepsakes and Treasures", where there is a Diabolical Mastermind crime boss Mr. Alice who likes to have sex with attractive young men. Similar to the Layer Cake example, the Villain Protagonist insists that this predilection does not make Mr. Alice a "poof". (Many older cultures would agree; whom a powerful man penetrated did not matter, it added to his power regardless, and women were sometimes seen as inducing unmanliness.)
- In the Italian mystery novel The Terra-cotta Dog, the hero, Inspector Montalbano meets with feared ganster "Tano the Greek". The narrator wryly informs the reader that Tano gained this knickname not from his heritage or any appreciation of classical art, but rather certain behavior which has gained association with the ancient Greeks.
- The crime lord Blood in Gene Wolfe's Book of the Long Sun.
- In Motherless Brooklyn, two mob bosses are caught unaware holding hands, quickly withdrawn once they know they're being watched.
- Joel Cairo, Caspar Gutman, and Wilmer Cook in Dashiell Hammett's The Maltese Falcon. Hammett refers to Wilmer as a "gunsel," meaning a gay concubine, but his editors assumed the word meant a gunman, which Wilmer also is. Most contemporary readers make the same mistake.
- Caprica: Sam Adama is hitman in the Tauron Mafia, he talks to his nephew William about the days in the old neighborhood when he'd keep striking out with guys while his brother Joseph got all the girls. This is a subversion in the sense that the Twelve Colonies have no discrimination or stereotyping against homosexuals and bisexuals and never have, so the fact that he's gay is completely non-significant (the word doesn't even exist). Sam also wears a wedding ring, as he is Happily Married to Larry.
- Cedric and Bob, the gay Latino street toughs from Seinfeld
- In the House episode "Mob Rules" it turns out that the patient is entering witness protection because he's secretly gay, and the only way he can survive coming out of the closet is to leave the family.
- Life On Mars had at least one, giving Gene Hunt opportunity to express his "enlightened" views on homosexuality.
- In Ashes to Ashes they discover a gayngster and Ray reacts with disbelief.
- Vito on The Sopranos. A straight deconstruction as the other gangsters find it disgusting, his only defender is given a hard time, Vito has to flee and is eventually killed for being gay.
- The Wire
- Omar Little, though he's not, in fact, a member of any actual organization and is instead a freelance stick-up man.
- Snoop plays this straight, as the bloodthirsty hitwoman for Marlo's crew; however, while she is certainly butch, to the point of being frequently mistaken for a teenage boy by audiences, there is only one line of dialogue that references her sexuality, and that in a fairly oblique way ("I'm just thinking about some pussy." / "Me too, man."). While the actress who plays her is openly gay, there is some debate amongst viewers as to whether the character is.
- Noah's Arc had rapper Baby Gat, who had a mostly one-sided infatuation with main character Noah.
- The C4 comedy drama Shameless
- Mickey Maguire is gay, and also a member of the local criminal family (although the Maguires have calmed down a bit since they became more prominent characters). Needless to say, his family are homophobic, so a frequent sub-plot is to have him worrying about when and how he's going to tell them. Also, despite being thuggish, Mickey has a few Camp Gay traits, and Hilarity Ensues when he says or does something effeminate in front of his Father or Brothers.
- Roscoe, one of Paddy's gangland rivals. When Shane follows him into the toilets and tries to listen in on his conversation through the glory hole, he gets something of a surprise.
- The Book of Daniel had a gay character, Michael Vaporelli, who was heavily implied to be part of the mafia. He came out in one of the unaired episodes.
- An episode of My Name Is Earl revolves around the titular character discovering that the respective leaders of the black and latino prison gangs are in love.
- An episode of Lie to Me involves two gayngsters who are found out by Torres' awesome gaydar. Which she most likely developed, along with her ability to read faces, because of her abusive father...
- The Shadow Line has Bob Harris and his incredibly camp boyfriend Ratallack.
- The topic of at least two Mad TV sketches.
- Two gangsters are trying to drive each other out of town, but one of them is freaked out when the other makes repeated sexual advances at him during their fight. At the end it's revealed that both of them are gay. The first gangster was just concerned that the other was still involved with another guy.
- In another, a trio of mafia men are introduced to a new capo, who has a reputation for being scary and ruthless. He repeatedly agressively berates the three of them for certain transgressions, but each time he gradually starts speaking like an effeminate gay man, and when he's finished, leaves the room for a little while. This eventually causes the gangsters to notice that their new boss is certainly scary, but gets a little "elegant" in his tirades. Finally, when the boss threatens to kill one of them they are suddenly interupted by two policemen, but these also turn out to be camp gay.
- One of the old gangsters in the Urban Gothic episode "The Boy's Club" was gay; we learn this when he reacts rather...violently... to being called a "poof", stating that "he isn't a poof, he's a homosexual."
- This was a direct Ronnie Kray quotation.
- The Mafiya member Isaak Sirko in Dexter. Points out to the protagonist it's Not So Different from being a serial killer as they are both outcasts who have to maintain a secret dual life.
- Played for tragedy in the Castle episode That 70s show — because it was the 70s, the gangster couple had to stay extremely deep in the closet, and one of them was eventually murdered by a jilted woman.
- There is supposedly a gay mafia on Will and Grace and Jack has supposedly run afoul of them. Will doesn't believe it until he's confronted by their leader, played by (who else?) Elton John.
- In the Blakes Seven episode "Gambit", Krantor, leader of an Outlaw Town, is strongly implied to be in a sexual relationship with his Camp Gay sidekick Toise.
- Morrissey's "The Last Of The Famous International Playboys" is sung from the perspective of a gayngster groupie. It also references the Krays.
- A common theme on gangsta rap "diss tracks" is to question other people's sexuality.
- The BBC Radio 4 serial G. F. Newman's The Corrupted is set in London gangland at around the time the Krays are first making their mark, and naturally features a few references to this. The main character, a teenager who becomes part of a rival organisation to the Krays, is a cross-dresser who spends some time as the kept boy of a prominent MP, and when he has sex with a woman he doesn't see what the fuss is about.
- The Bare Knuckle/Streets of Rage series for the Sega Genesis had a stereotypically gay miniboss named Ash. Of course, he got Lost in Translation when the game was ported to the United States.
- El Burro in the original Grand Theft Auto. After you complete level 4 (second level of San Andreas), you are summoned to his club where he tells you he is "gonna reward you personally this time!" Funnily enough you then zoom over to Vice City for the next level.
- Grand Theft Auto: San Andreas: OG Loc. The player first encounters him when he's leaving prison and wants to hook-up with his prison-boyfriend, though of course OG is in complete denial. Instead, the player ends up killing the boyfriend. So, yeah. OG Loc later does a radio interview where he stresses his macho-ness.
- Gay Tony in Grand Theft Auto IV: The Ballad of Gay Tony is not a gangster himself, but runs a nightclub that has regular dealings with gangster. And his protege Luis, while also not affilaited with and gangsters, does a lot of freelance work for gangsters.
- Many games in the Fire Emblem franchise feature two bandits, one pink, one blue that are quite clearly masochistic homosexuals.
- In the "Death on the Mississippi" mission of Hitman: Blood Money, the player has to infiltrate a steamboat and kill members of a gang whose boss is a gay Scary Black Man. The boss likes to dress like a sailor, all his crew are dressed as sailors, like the pursuers and waiters. When he has free time he likes to make his cooks and waiters goes to his room and have gay sex with him. This is learnt when Agent 47, if he disguises himself as a waiter or a cook, goes to the kitchen, and a employee will tell him to take "a present to the boss" and "to be proud about it" (the present is a birthday-cake, and the extra surprise is the routine gay sex that waiters have to deal with).
- Aria T'Loak, the "Pirate Queen" of Omega in Mass Effect 2, is omnisexual like all asari, but it's obvious she prefers the company of women upon playing through the Omega DLC of Mass Effect 3.
- Sera in Dragon Age: Inquisition is an elven archer and rogue who works for the Friends of Red Jenny, a Karmic Thief gang that targets nobles for valuables and mischief to help out the common people of Thedas. She is also a romance option for female Inquisitors only.
- Kanji in Persona 4; he isn't in a gang, or part of an organized group of any kind beyond the Investigation Team, but he acts and dresses like he is in order to cover up the shame of his enthusiastic love of traditionally-feminine things.
- Final Fight has Roxy and Poison. Roxy is, as a fancier of Poison, somewhere in the LGBT spectrum. And she's in a street-fighting gang. As for Poison... well, you can pick and choose (literally - latest Word Of God is "pick for yourself") between whether she's a woman, a cis woman, a transsexual woman, or an intersex woman, so she could fit in this as well.
- Assassin's Creed: Syndicate has Maxwell Roth, a brutal Victorian-era London Gangster and the mastermind of the Templar-controlled Blighters street gang. He has insane amounts of Foe Yay with the game's male protagonist Jacob Frye, and Word of Gay confirmed that his overtures towards him, such as giving him a Take-That Kiss before dying, were not intended to spite him but out of genuine attraction to him.
- Jacob himself counts as well as the co-leader of the Rooks street gang along with his twin sister Evie, since the same writer who confirmed Roth's homosexuality also said in the same interview that at the very least Jacob was written to be bi-curious, and his brief partnership with Roth was partly a form of self-discovery.
- Played for Laughs in a scene of Rose Guns Days Last Season. In order to infiltrate the hotel where Rose is confined, the heroes make use of their girls' charms to distract the guards, passing them as ladies of the night. The last guard tells them to leave him alone, saying that he's not interested in womenÖ before suddenly taking a liking to Charles' "beautiful hands". Though it wasn't part of the plan, they just go with it anyway.
- Boys Love game Lucky Dog 1 is all about this.
- Ryuuhei in Maji De Watashi Ni Koi Shinasai is the most typically "thuggish" of his siblings to boot. Though that might be because he's the only male sibling. He also loves fighting, loves sowing chaos, and loves rape (which Yamato found out in a very lovely Bad End).
- Leon Ratterly from Friendly Hostility and Other People's Business works as a hitman for the Creed Corporation. He varies between Bad Boy Lover and Bastard Boyfriend towards his husband, but he's a great big teddy bear when it comes to his daughter. Naturally, the fandom loves him.
- The titular character of Humon's Niels is kinda this: he's an openly bisexual mob boss. His second in command, Duncan, is a little less open, but also falls into this: he and his wife are in fact Niels's lovers.
- Izm of the Hedone High series is a bisexual drug dealer. he shows no attraction to girls, however. He's more interested in his best friend A.E.D
- Pogo from in DemonoftheUnderground seems to be heading that way when he got roped into the East Sphere by their leader and eyed his naked male teacher and insisted on sharing a bed with him.
- When She Was Bad has Connor Hammond, nephew to local kingpin Jakob Hammond. He isn't out to the other members of his gang.
- According to Aranea of Homestuck, the Felt are this.
8ut first it 8ears pointing out that while for humans reproductive relationships are exclusively heterosexual, and for trolls they are 8isexual, for leprechauns they are exclusively homosexual. Yes, you heard right. That means the Felt are all super gay. A graphic description of their reproductive process is as follows.
- Basically the entire pitch of Griefer Belt
- In The Gamers Alliance, Galeras Matheson is one of the heads of the Matheson Crime Family and is openly gay.
- Light/Kira and Mello in Death Note: The Abridged Series (kpts4tv).
- Alberto Falcone from The Joker Blogs
- The Gay Cholo.
- Inevitable  example: Deathlist, a ruthless cyborg killing machine who has slain more superheroes than any other villain, and his lover Chessmaster. They are the only ones who have ever dared attack Whateley Academy directly, though they paid the price for doing so by having their minions slaughtered and ending up on the run from both heroes and villains alike.
- Gangstalicious from The Boondocks, a gangsta rapper who is also a semi-closeted homosexual. As seen in his "Homies Over Hoes" music video (with misogyny galore).
- The Booty Warrior seems to be another example. He's first seen on a spoof of To Catch a Predator where he reveals he didn't come to have sex with a boy, but that he knew he was on the show and came to rape Chris Hansen himself. He's later seen in the same episode 5 years later when Tom accompanies Huey and Riley on a scared straight program to a prison, where he's an inmate. After going on a monologue about how booty is everything, and forcing Tom to strip down to his underwear, he tries to rape Tom, wielding a shiv stolen from Tom who had brought it to protect himself from being prison raped. Tom flees into the prison as the guards try to apprehend the prisoners. This causes a prison riot where the prisoners gain control over the prison, and start to make a list of demands in exchange for their hostages. The Booty Warrior doesn't seem to care, though, searching the entire facility trying to rape Tom.
- Referenced in Futurama:
Fry: I know Big Vinnie said he was giving me the kiss of death, but I still think he was gay.Leela: Did he use his tongue?Fry: A little!