A homosexual organized crime member. This is most common in British works, perhaps because one of the Kray twins fits this idea. Similarly, this is especially true when a work is set around the time when the Krays lived. 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.
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.
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 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.
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.
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.
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".
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.
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.
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.
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.
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.
Sam Adama from Caprica. A 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.
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.
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...
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.
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 prominant MP, and when he has sex with a woman he doesn't see what the fuss is about.
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.
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 is tasked into infiltrating a steam-boat and killing members of a gang whose boss is a gay Scary Black Man. He likes to dress like a sailor, all his crew are dressed as sailors, such as pursuers and waiters, but not the engineers or the guards of the ship. He have waiters and many rooms in his ship, because it's a drug cartel covered in a "steam-boat-disguise", and 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 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). More or less, this is described in the mission briefing. Also, there's a bathroom in the captain's deck that's filled with a spewed bottle of wine over the floor. Anyway, all of his sailors seems to express gay sexual preferences, and the way they talk... You'll have to Figure It Out Yourself. Or buy the damn game!
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 LBGT 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.
The titular character of Humon'sNiels 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.
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.
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!
Not at all repressed, but Ziro the Hutt of Star Wars: The Clone Wars was apparently a Camp Gay gangster/nightclub owner, at least until a later story arc revealed his romantic relationship with Femme Fatale Sy Snootles, making him Camp Straight. However, Hutts being hermaphrodites, their definition of gay or straight may be a mite fuzzy in either case.
When the Springfield Mafia want to film a porn movie in Homer's house in The Simpsons, Homer first groans he doesn't want people shooting gay porn in his house, as he thought they were the "gay mafia". He gets slapped for the remark.
Another episode has an actual, homosexual "velvet mafia" with a float in a gay pride parade.
Next time you're in your local gay porn shop, head to the "ethnic" section and grab the first title you see. Odds are it will have a gayngsta theme—as if that's the only thing gay men of color (or white guys attracted to them) are interested in—even if that only means the actors wear bandannas and Timberland boots during sex.
Ronnie Kray, of the London dopplegangsters, the Kray twins. Famously killed a man, in public, for having called him a "fat poof".
Ernst Rohm and other leaders of the Sturmabteilung (the original Nazi Brownshirts) were not very discreet about their homosexuality. The Party mostly dismissed accusations of homosexuality as Jewish propaganda until they decided the SA were a threat to Hitler's power. Once that happened, Hitler used Rohm's homosexuality as justification for his murder to quell outrage among the SA during Night of the Long Knives after he was no longer useful to Hitler's ends.
Gay skinheads are actually a recognized subculture, usually crossing over with gay biker communities. As there are various categories of skinheads (a fair number of which look upon the Nazis with loathing), it's not really a commitment to Nazi ideals as much as it is a fetishistic attraction to the white punk aesthetic.