Gayngster

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.

— The Young Protectors

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 British Gayngsters are No Celebrities Were Harmed fictionalized versions of him, to some degree. In the US, the Gayngster is often a Scary Black Man or Latino, though it's not entirely uncommon to see someone White, especially if they are Italian or Irish. 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. "Banjee" has long been both an LGBTQ and an urban slang term to refer to a young gay black or Latino male who dresses and acts in an unambiguously urban macho manner.

Not related to Gayngst, but overlap is possible. Also see Armoured Closet Gay and Manly Gay, which frequently overlap as well.

noreallife

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Examples:

Anime & Manga

• Nirasawa from Bi no Kyoujin is a Straight Gay Bishōnen evolving in the highly homophobic Yakuza world where he becomes the leman of Kabu, the heir of his clan. Kabu is particularly intrigued by Nirasawa's shrewdness and his resilience under torture which prompted him to take him under his wing as his Battle Butler.
• In the Cowboy Bebop episode "Waltz for Venus", 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.
• Finder Series: Asami is the local crime boss stalked by Intrepid Reporter Takaba.
• 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.
• Ranmaru from A Foreign Love Affair is also a young Yakuza clan heir who marries his beard wife while falling for the cruise ship's captain who hosts their lavish wedding soirée.
• Ichi the Killer: Kakihara appears to be this for Boss Anjo, but he explains that he's actually just In Love with Your Carnage (the punishments Anjo gave him).
• 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.
• Inuyasha: Remember Jakotsu of the Band of Seven? An extremely creepy Depraved Gayngster Yandere.
• Minor villains Squalo and Tiziano from JoJo's Bizarre Adventure: Golden Wind, they are dedicated enough to each other than Tiziano doesn't hesitate to intercept a salvo from Aerosmith meant for Squalo. Also two members of La Squadra di Esecuzione, Sorbet and Gelato, were rumored to be a gay couple, which is more heavily hinted at in the anime adaptation. 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. However, there are moments in the story where the protagonists express strong emotional feelings, akin to romance, for someone of the same sex. Abbacchio's feelings for Bruno is a good example of this. There are also times when two main male characters, Giorno and Mista, are placed in precarious situations simulating sexual acts.
• Similarly Kizuna also focuses on the Yakuza setting, but in a rather less grim and more romanticized way.
• Tsukuyomi in Negima! Magister Negi Magi is basically a terrorist (as far as Sayo is concerned). She's also an extreme Psycho Lesbian.
• Kano from Okane ga Nai is also an example of this trope, of the Loan Shark variety. Likewise, his subordinate Homare Kuba is also an example, being a very dangerous brawler who also falls for his boss' lover Ayase, a dainty 18 years old boy.
• The great Mr. 2 Bon Clay from One Piece is a rare Camp Gay version of this trope.
• Paranoia Agent features a yakuza boss who's into younger men.
• A lot of members from the mafia in Reborn! (2004) have extremely questionable sexuality... but for a more obvious, straightforward example, Lussuria from the Varia is shown outright to be gay.
• In Shadow Star, a gang of thugs calls in a gay gangster for the sole purpose of raping the Wholesome Crossdresser who just gives an Unsettling Gender-Reveal before they kill the crossdresser.
• 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.
• Nico of Tokyo Ghoul, a standard Camp Gay who is among the more prominent and influential members of ghoul gang, the Clowns.
• Buppa, one of the mob bosses in Tokyo Tribes, is a Fat Bastard Depraved Bisexual who rapes boys so hard they explode. Really.
• Yashiro from Twittering Birds Never Fly is a notoriously depraved example of the trope, being capable of beating up his foes singlehandedly while shamelessly using his position and attractiveness to seduce and screw with his superior or his fellow mob bosses, which elicits disgust and disbelief from his cohorts who greatly fear him but who also wonder how these dangerous mobsters could have sex with a man like him.
• 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.

Comic Books

• 100 Bullets:
  • The second volume 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.
• In one of DC's Milestone Comics' Blood Syndicate, 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.
  • According to Word of God, Tech-9 and Fade were lovers on the downlow. See here.
  • This is carried over to Blood Syndicate (2022), although in this version, Fade appears to not be in the closet.
• One Grendel story has Hunter Rose intervening to stop members of a gang he's taken over from killing a Gayngster out of homophobia, making very clear that he views such prejudice as primitive and hypocritical.
• Gilbert Hernandez's "Poison River" story in Love and Rockets features several Gayngsters.
• 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.
• Palumbo, one of the heads of a post-WWII Italian crime family in Twelve Reasons to Die, is a closeted gay man. Starks makes it look like he's having an affair with another head's wife in order to get orders to kill him so that a position in "The Twelve" will open up, but doesn't seem to care about Palumbo's orientation.
  Palumbo: Do me a favor, Anthony. Don't tell them. Please.
  Starks: Ain't they business.
• Ultimate X Men's Colossus was a Russian Mob enforcer and heavily closeted gay and mutant for years in his Back Story.
• 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.

Film — Live Action

• Meredith from 44 Inch Chest is another great Ian McShane Gayngster moment.
• In Birds of Prey (2020), Roman Sionis/ Black Mask and his number two Mr. Zsasz are very physically and emotionally intimate with each other and strongly implied to be a romantic couple, although it's never explicitly stated.
• 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.
• In Cold Pursuit, two of Viking's crew, Mustang and Dexter, are a couple and are hiding it from the rest of the gang.
• Corky Romano: Peter, one of the main gangsters, is gay though he denies it for most of the film.
• Eighties Irish thriller The Courier (not to be confused with the 2021 film of the same name) features crime boss and drug dealer Val, who is heavily implied to be gay (picking up a male sex worker) but repressed and messed up about it(instead of having sex with the guy he picked up, he interrogates the poor man about his childhood and insists that he must have been molested).
• Irish coming-of-age film Cowboys And Angels features a closeted gay or bisexual drug dealer, Keith. Late in the film he confesses to the (heterosexual) protagonist that he's attracted to him, and implies that he's been forced to be closeted because of his involvement in crime.
• 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.
• 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.
• 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 Gangster" from Gangster No. 1 is hinted at being a latent homosexual due to his misogyny and fixation on glamorous crime prince Freddie Mays.
• Ricki from Gigli. A lesbian gangster, for a change.
• Hammett, a 1982 fictionalized account of Dashiell Hammett's life before he wrote The Maltese Falcon, is also quite overt about the Gutman/Wilmer expys English Eddie Hagedorn and "The Punk."
• In High Heels and Low Lifes, Mason's boss is a Kerrigan, an old-school gay London Gangster with a veneer of civilisation (played by Michael Gambon). Behind his back, Mason refers to him as "the old poof", but Kerrigan is the one person that hard man Mason is scared of.
• In Order of Disappearance: The Count's lieutenant and one of his soldiers are in a relationship, which they keep from the others (who are presumably homophobic). You can see his lieutenant is visibly distraught when the Count kills his lover, but he covers himself and stays loyal.
• 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 Noël Coward.
• The Killing Gene: Daniel is a gangster who, along with the rest of the gang, raped Jean and murdered her mother. He's also sleeping with and informing for Eddie, a police officer who's investigating the gang, suggesting he's at least bisexual.
• 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".
• Real-life example Ronnie Kray is one of the Villain Protagonists of Legend (2015), though here, he's just gay instead of bisexual. Ronnie is one of the manliest and most violent gangsters in 1960's London, and he very much doesn't like people trying to demean him with his sexuality. As he puts it, "I'm a homosexual. There's a difference. I'm a taker, not a giver. I'm not a faggot."
• The subtext of Little Caesar is that Edward G. Robinson has a crush on Douglas Fairbanks.
• Lucky Number Slevin features the character called "The Fairy,'' the gay son of another gangster called "The Rabbi."
• The 1931 version of The Maltese Falcon, being from The Pre-Code Era, is even more overt with the Gayngster theme. Gutman caresses Wilmer's cheek before betraying him, and Spade calls Wilmer Gutman's "boyfriend."
• 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 Mechanic (2011): The first contract killing that Bishop gives to his protégé Steve is to kill Burke, a Manly Gay rival hitman. Fortunately he Has a Type — young men from troubled backgrounds who own cute dogs. So Bishop buys a chihuahua from the animal shelter and tells Steve to start exercising it around where Burke goes for coffee. This undoes the trope's aversion in the 1972 original. The relationship was originally written as explicitly gay but producers couldn't raise funding and actors refused to consider the script until it was changed.
• The protagonist of Moonlight is attracted to men. In the third act, it's shown that he ended up a drug dealer. He isn't repressed but he isn't open either. Chiron never outright mentions if he's gay or not, but the film ends with him accepting his sexuality and affections towards Kevin.
• North By Northwest has Leonard, Martin Landau's character (according to Word of Gay).
• 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 - and possibly about his own sexuality.
• Perrier's Bounty has Ivan and Orlando, a couple of Manly Gay henchmen.
• The 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.
• The Punisher (2004) has Quintain Glass, Howard Saint's best friend and second-in-command as a closet gay... at least from him. His wife apparently knew. This comes 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 mobster's wife as having an affair. The boss ends up killing his friend and wife, but not before slapping her for "insulting" his memory just to save her own skin.
• 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 has a hard time accepting it. For everyone else, the fact that Bob is awesome overrode the fact that Bob was gay. 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".
  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?
• Sexy Beast: Teddy Bass, "Mr. Black Magic" himself. Teddy attends Roman-style orgies to meet wealthy and powerful men and steal from them.
• There's also a bisexual/lesbian couple of hitmen in Smokin' Aces. Vague hints of Gayngst as well.
• Ten Dead Men: Although not explicitly stated, Garrett and Parker are strongly implied to be a couple. They only operate as a pair, and Parker is especially touchy-feely: doing things like reaching out to stroke Garrett's hair.
• Traffic (2000): Frankie Flowers, the Assassin working for The Cartel. A cop with exclusive knowledge of this uses it to catch him at a gay bar, pretending to proposition him for sex.
• Trouble in Mind: Hilly Blue (Divine) is the leader of the crime syndicate, slightly Subverted by the fact that he's in the Transparent Closet.
• 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." King even brings it up with Squash after he comes out after all these years.
  King: I've known you for years.
  Squash: You've known a lot of guys, Boss.
  King: You were an All American. I never met a meaner, rough, tough, son of a bitch football player all my life!
  Squash: Well, if you didn't want the guys on the team calling you 'queer'... You became a mean, rough, tough, son of a bitch football player.

Literature

• Harry Stark in Jake Arnott's The Long Firm is intentionally something of an No Celebrities Were Harmed version of Ronnie Kray.
• 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.
• In the Modesty Blaise novel I, Lucifer, one of the hitmen sent after the head of the French secret service wears make-up, frilly clothes, and dressed hair, is described with feminine mannerisms, and is suggested to be in a relationship with one of the others. It's made clear that he's not in any way less dangerous than anyone else on the team.
• In Motherless Brooklyn, two mob bosses are caught unaware holding hands, quickly withdrawn once they know they're being watched.
• Myth Adventures: Don Bruce, 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.
• Egon the Poof, a Berlin gangster in O.G.P.U Prison by Sven Hassel that Porta and Tiny make various attempts to kill off.
• Six of Crows: Jesper is openly pansexual. He is also a incredibly accurate sharpshooter who works as a hitman for one of Ketterdam's many gangs to support his gambling addiction.
• Gino Fish in Robert B. Parker's Spenser, Sunny Randall and Jesse Stone novels.
• 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.
• Eric Flint's Timestrike has an openly gay ex-hit man as one of its main characters.

Live-Action TV

• In Ashes to Ashes (2008) they discover a gayngster and Ray reacts with disbelief.
• Barry: NoHo Hank's rather flamboyant and even a little effeminate, and seems to have something of a crush on Barry. He also starts falling in love with Cristóbal in Season 2. In the finale, he declares his love for Cristóbal. Season 3 shows them as a happy couple, while both are dangerous mobsters.
• Big Sky: The criminal duo Paul and Snail in "All Kinds of Snakes" are a couple.
• In the Blake's 7 episode "Gambit", Krantor, leader of an Outlaw Town, is strongly implied to be in a sexual relationship with his Camp Gay sidekick Toise.
• 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.
• It's heavily implied that Gus Fring of Breaking Bad and Better Call Saul was more than friends with his first meth cook, Max. Nothing's ever confirmed, but Hector Salamanca makes a disparaging comment about it in Better Call Saul.
• Caprica: Sam Adama is a hitman in the Tauron Mafia, and 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.
• 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.
• Criminal Minds: Evolution: In "True Conviction", Silvio was a member of a Latino gang, as was his boyfriend, which they stayed in the closet about due to this being considered unnacceptable in that culture.
• Dexter: The Mafiya member Isaak Sirko points out to the protagonist it's not that different from a cop being a serial killer as they are both outcasts who have to maintain a secret dual life. Although he does appreciate the irony that he expected to be killed if his secret ever came out, but instead his bosses put a hit out on him for completely different reasons.
• The Fallen Angels episode "The Professional Man" is about Johnny Lamb, a homosexual elevator operator who moonlights as a hitman. He's sleeping with the boyfriend of his boss, but unfortunately the boss orders his boyfriend killed. Consummate Professional that he is, Lamb carries out the hit despite having real feelings for him. Lamb isn't made to feel any better by his boss implying that he'd make a good Replacement Goldfish.
• In the Musical Episode of The Flash (2014), Joe's counterpart in the musical world is a mob boss. Martin Stein's counterpart appears to be his lieutenant and enforcer ... until the Iris counterpart calls them both Dad.
• Gang Related: The member of the Lords gang who gives up the shooters turns out to be a closeted gay man with a boyfriend. He agrees to go into Witness Protection in the deal if they're together. They marry before going in, with the cops commenting he probably likes the fact they can be open about their relationship now.
• Season 3 of Gotham revealed that Oswald Cobblepot, aka the Penguin, is in love with Edward Nygma.
• 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.
• In the Dark: Sam, a fierce, no-nonsense gang enforcer, turns out to be a lesbian.
• Jane the Virgin: Rose is an international crime boss and a lesbian.
• Law & Order: Organized Crime:
  • Nova is a Black gangster who's also a lesbian. It turns out this is fake though: she's an undercover cop.
  • Albanian gangster Albi turns out to visit gay clubs, and is deeply closeted since he comes from a homophobic culture. He nearly kills Elliot (who discovers this) in fear of being outed to his gang.
• 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...
• Life On Mars has at least one, giving Gene Hunt an opportunity to express his "enlightened" views on homosexuality.
• The topic of at least two MADtv (1995) 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 aggressively 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 interrupted by two policemen, but these also turn out to be camp gay.
  • A hip-hop variant with rapper Defcon-1, an openly gay gangsta rapper who threatens to kill anyone who starts trouble over it. Semi-inverted as he barely acts in a stereotypically gay manner.
• Dinsdale Piranha in the Monty Python episode "Face the Press," being a Ronnie Kray parody, is a brutal London Gangster who nails people's heads to the floor, has a "warm interest" in boys' clubs, sailors' homes, and the Household Cavalry, and dated a Drag Queen.
• 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.
• Noah's Arc has rapper Baby Gat, who had a mostly one-sided infatuation with main character Noah.
• Orange Is the New Black: Alex — former smuggler for an international drug cartel, and a lesbian — is the most notable example, but seeing as it's a show about a women's prison, full of bi-and-lesbian criminals, there are other characters with shades of it as well.
• Penny Dreadful: City of Angels: Fly Rico appears to be bi at least, given he has a casual threesome with Mateo and Rio (which he initiates by kissing the guy). He's also a feared pachuco gangster.
• The Rockford Files: Paul Silvan from "Requiem for a Funny Box" is one of the earliest examples on TV. He's a mobster keeping his relationship with a popular comedian secret due to family pressures.
• Seinfeld has Cedric and Bob, the two very gay street toughs who Kramer always ends up running into. They steal Elaine's armoire while she has Kramer guarding it, harass Kramer for not wearing an AIDS ribbon at an AIDS walk, and catch Kramer at exactly the wrong moment while he's trying to stomp out a Puerto Rican flag he accidentally set on fire during Puerto Rican Day.
• The Shadow Line has Bob Harris and his incredibly camp boyfriend Ratallack.
• The C4 dramedy Shameless (UK):
  • 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. His counterpart in the American remake is also this, albeit played up more for drama.
  • 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 Sopranos:
  • Vito Spatafore is a straight deconstruction as the other gangsters find it disgusting, his only defender is given a hard time, and he has to flee and ultimately gets whacked for it by the homophobic Phil Leotardo and his men. The Sicilian mafia is not known for its tolerance.
  • David Chase confirmed on the Talking Sopranos podcast that Phil Leotardo is an Armored Closet Gay. Hence he was so angry when his cousin-in-law, Vito, turned out to be gay.
• Tidelands (Netflix):
  • Lamar is the lieutenant of The Queenpin Adrielle, and secretly involved with Dirty Cop Paul Murdoch.
  • Adrielle herself is later shown to be a Depraved Bisexual with a mutual attraction for her Psycho Lesbian henchwoman Leandra.
• Urban Gothic: One of the old gangsters in the 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.
• Whitechapel (TV Series): In the second season, Real Life bisexual gangster Reggie Kray is brought up (he's described as gay in the series), serving as inspiration to his supposed son Jimmy Kray, who presents himself as being the same. However, he may be lying as his "boyfriend" is a girl who's pretending to help him fill the role.
• 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.
• Your Honor: Big Mo is a female crime boss who it turns out has a girlfriend.

Manhwa

• Jin Lee and Yeong Joon in 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.

Music

• Todrick Hall's song "Gay Gangsta" is about this.
  "And if the cops got questions, no can do, no can tell,
  All I gotta say is, 'Whoops! I broke a nail.'"
• Morrissey's "The Last Of The Famous International Playboys" is sung from the perspective of a gayngster groupie. It also references the Krays.

Radio

• 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.

Tabletop Games

• Shadowrun has an entire motorcycle gang called the Leather Devils, effectively answering the question of what would happen if a gay MC went outlaw. They are just one of many gangs in Seattle, though their focus is mainly on prostitution, porno, and blackmail, with the occasional bit of wild highway mayhem.

Video Games

• Assassin's Creed Syndicate:
  • Maxwell Roth is a brutal Victorian-era London Gangster and the mastermind of the Templar-controlled Blighters street gang. He has insane amounts of Foe Romance Subtext 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.
• V in Cyberpunk 2077 can be played as this. While V can never become a fully-fledged gang member, they can take different jobs from fixers who have strong ties to them (like Wakako or Padre). While all Vs count for this trope, the ones with a streetkid lifepath are openly stated to be raised by different gangs. No matter their sexual orientation, V will always be a tough-as-nails mercenary. While the player can customize V's looks and make them look as camp as they want, V can't really act in a camp way (and, since kitch is the hottes trend in 2077, their looks might not mean much in-universe), so untill V hires a same-sex joytoy or starts dating Kerry Eurodyne or Judy Alvarez, nothing really points to them being gay/bi.
• 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.
• Far Cry 3:
  • Bambi "Buck" Hughes is not a gangster, but he is a mercenary hired by Hoyt Volker, the leader of a massive slaver syndicate operating from the Rook Islands. As for being gay, he's keeping Jason's friend Keith as a Sex Slave to force Jason to find a Chinese knife for him, and he's pretty brutal with him. And when Jason finds Keith, Buck's eager to add Jason to his list of conquests. Apparently, he's not above "taking his meat rare" if he feels like it.
  • Hoyt Volker himself briefly plays this for Faux Yay Black Comedy. After cutting off Jason's ring finger in a poker tournament, he says "Aw, Jason, now we'll never be married." Apart from this, we never learn anything about Hoyt's sexual preferences. He's more defined by selling slaves and killing people than raping men.
• 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.
• Many games in the Fire Emblem franchise feature two bandits, one pink, one blue that are quite clearly masochistic, and in some cases incestuous, homosexuals.
• Grand Theft Auto:
  • 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.
  • Implied in the case of Kazuki Kasen in Grand Theft Auto: Liberty City Stories, whose wife Toshiko states that he "prefers the company of men" and hires Toni to kill him because she wants out of a loveless marriage.
  • 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 gangsters. And his protégé Luis, while also not a gangster, does a lot of freelance work for gangsters.
• Hitman: Blood Money: In the "Death on the Mississippi" mission, among the player's targets is Skip Muldoon, who runs a cruise ship business on the Mississippi river, and who is also a Depraved Bisexual gang lord who is very bluntly implied to force his male ship staff to sleep with him.
• In Mafia III, Nicki Burke, a high-ranking member of The Irish Mob, is gay.
• Mass Effect:
  • 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.
  • Captain Gavorn, a minor Non-Player Character who serves as an enforcer in Aria's organization, is heavily implied to be gay in video footage you can view in the Lair of the Shadow Broker DLC for Mass Effect 2.
  • Reyes Vidal in Mass Effect: Andromeda is a human Exile who has established a name for himself as a smuggler and criminal on Kadara, and is bisexual and available as a romance option for a male or female Ryder. Bonus points for being revealed as the Charlatan, the criminal mastermind behind the Collective.
• Persona 4: Kanji isn't in a gang, or part of an organized group of any kind beyond the Investigation Team, and he's only Ambiguously Gay with a side of Sweet on Polly Oliver, but he acts and dresses like a Japanese Delinquent in order to cover up the shame of his enthusiastic love of traditionally-feminine things.
• Streets of Rage 3 for the Sega Genesis had a stereotypically gay miniboss named Ash. Of course, he got Bowdlerized when the game was ported to the United States.

Visual Novels

• Ryuuhei in Majikoi! Love Me Seriously! 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).
• 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 women… before suddenly taking a liking to Charles' "beautiful hands". Though it wasn't part of the plan, they just go with it anyway.

Webcomics

• Demon Of The Underground:
  • Pogo, the protagonist, 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.
  • Considering that the majority of the Underground are descendants of a Penal Colony, are in the middle a four-way gang war, and there is not real stigma against same-sex partners, a large part of the cast fit the trope.
  • Merritt, a secondary character in the main comic and protagonist of the prequel book Devoted, is a high ranking officer of the East Elite Squad and explicitly homosexual.
• 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 Domestic Abuser towards his husband, but he's a great big teddy bear when it comes to his daughter.
• Griefer Belt describes itself as "a Slice of Life series about queer criminals in the black market".
• 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.
• According to Aranea of Homestuck, the Felt, a group of alien mobster mooks are all gay.
  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.
• 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.
• Tielo and Fergal of Otherworldly. Members of the Unseelie Mob (The Fair Folk version of organized crime), and also fiancés.
• The webcomic Rechargeable is described on its website as "A queer gang in 2100 Australia".
• Wet Sand: TJ is a boss of the gang K35 and bisexual, having dated women and been Ian's lover for years. Ian, who often invites guys over to his place, is a former Gayngster, having left K35.
• When She Was Bad has Connor Hammond, nephew to local kingpin Jakob Hammond. He isn't out to the other members of his gang.

Web Original

• 50% OFF, The Abridged Series of Free! changes Nagisa from an Ambiguously Gay high school swimmer to a gangster with an obvious crush on Rei.
• In The Gamer's Alliance, Galeras Matheson is one of the heads of the Matheson Crime Family and is openly gay.
• The Gay Cholo.
• Tails of the Bounty Hunter has Rellis Rottili, a mob boss in the Rottili Mafia organization who's also homosexual.
• Whateley Universe: 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.

Western Animation

• The Boondocks:
  • Gangstalicious is 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...
• Hazbin Hotel: Angel Dust was a ruthless member of the Mafia when he was alive, and was very gay. In his scrapped backstory, he was killed by his older brother Arackniss for being gay. In canon, he died of a drug overdose, but he was still on shaky terms with his brother due to his sexuality and it's implied that was a major reason why he turned to drugs in the first place. In hell, he's turned into an anthropomorphic spider demon who dresses in pink, wears knee-high boots, and has a tuft of fur on his chest that resembles a pair of very large female breasts. He's also an extremely famous gay porn star and has no chill when he wants to have sex with someone. Even after seeing how terrified Charlie and Vaggie were of Alastor, Angel very bluntly offers to give him a blowjob first chance he gets, even smugly saying it was Alastor's loss when he gets turned down due to Alastor being asexual. But the fact that he's turned the "gay" part up to eleven doesn't mean he's lost any of the "gangster" part of "gayngster". He's still willing to shoot up a territory at the drop of a hat, especially if his best friend Cherri Bomb asks him to.

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