->'''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.
-->-- ''Webcomic/TheYoungProtectors''

A homosexual member of organized crime. This is particularly common in British works set around the 1950s and 60s, as the notorious 1960s LondonGangster Ronnie Kray was fairly openly bisexual. Many fictional British Gayngsters are NoCelebritiesWereHarmed fictionalized versions of him, to some degree. In the US, the Gayngster is often a ScaryBlackMan 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. "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. May overlap with BadassGay, since [[DamnItFeelsGoodToBeAGangster crime is cool]]. Also see ArmouredClosetGay, ManlyGay



[[folder: Anime & Manga]]
* A lot of members from the mafia in ''Manga/KatekyoHitmanReborn'' have [[HoYay extremely questionable sexuality]]... but for a more obvious, straight-forward example, Lussuria from the Varia is [[CampGay shown outright to be gay]].
* Gauron from ''LightNovel/FullMetalPanic'' 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 [[StalkerWithACrush twisted and obsessive love]] for Sousuke, making him a pretty good example of being a StraightGay.
* There are plenty of yakuza characters in [[BoysLove yaoi]] anime and manga. For a start, Masa and Kai from ''Manga/{{Kizuna}}'', Ranmaru from ''Manga/IkokuIrokoiRomantan'' and Asami in Yamane Ayano's ''Manga/FinderSeries''.
** Not to mention the shoujo classic Manga/BananaFish.
* Tokyo Tribes: One of the mob bosses is a FatBastard who rapes boys so hard they explode. Really.
* Tsukuyomi in ''Manga/MahouSenseiNegima'' is basically a terrorist ([[FunnyBackGroundEvent as far as Sayo is concerned]]). She's also an extreme PsychoLesbian.
* Minor villains Squalo and Tizziano from the fifth arc of Manga/JoJosBizarreAdventure; and a couple [[spoiler: dedicated enough that Tizziano doesn't hesitate to [[TakingTheBullet intercept a salvo from Aerosmith]] meant for Squalo]]. Also the violent leaders of La Squadra di Esecuzione, Gelato and Sorbet, were rumored to be a gay couple. Everyone else, including the protagonists, comes off as almost CampGay due to their really weird clothes, but don't really show any attraction to the same sex. [[{{Asexual}} 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.
* The great Mr. 2 Bon Clay from ''Manga/OnePiece''.
* 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.
* ''Anime/ParanoiaAgent'' features a yakuza boss who's into younger men.
* Jin Lee and Yeong Joon in the Korean manhwa "Manhwa/KillMeKissMe" 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 ''Manga/{{Narutaru}}'', a gang of thugs '''calls in a gay gangster''' for the sole purpose of raping [[spoiler: the WholesomeCrossdresser who just gives an UnsettlingGenderreveal before they kill the crossdresser]].
* Arguably, Mello from Manga/DeathNote, if you believe the fangirls.
* ''Manga/InuYasha'': Remember Jakotsu of the Band of Seven? An extremely creepy {{Depraved|Homosexual}} [=Gayngster=] {{Yandere}}.
* In one episode of ''Anime/CowboyBebop'', 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 ''Anime/SpeedGrapher'' is implied to be gay and have a romantic quality in his devotion to his boss Suitengu. He and the other members of the TerribleTrio 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 ''Manga/WildAdapter'' 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 [[IfItsYouItsOkay just]] Kubota.
* Nico of ''Manga/TokyoGhoul'', a standard CampGay who is among the more prominent and influential members of ghoul gang, the Clowns.

[[folder:Comic Books]]
* The second volume of ''ComicBook/OneHundredBullets'' 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.
* ''ComicBook/UltimateXMen'''s Colossus was a Russian Mob enforcer and heavily closeted gay ''and'' mutant for years in his BackStory.
* Gilbert Hernandez's "Poison River" story in ''ComicBook/LoveAndRockets'' features several [=Gayngsters=].
* In one of DC's Milestone Comics "ComicBook/BloodSyndicate", 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 [[spoiler:Tech dies]].
** According to WordOfGod, [[spoiler: Tech-9 and Fade were lovers on the downlow.]] [[http://forums.comicbookresources.com/showthread.php?s=71c9f45abb28a972547a3d5e66620143&t=226749&page=6: See here.]]
* Phat from ''[[ComicBook/XForce 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 FauxYay 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 ''ComicBook/NikolaiDante'' included a homosexual {{Expy}} of [[ShoutOut both]] [[ComicBook/SinisterDexter Ramone and Finnigan]]. Very much the CampGay vibe, to go with the deadly.
* One ''ComicBook/{{Grendel}}'' story has [[DiabolicalMastermind Hunter Rose]] intervening to stop members of a gang he's taken over from killing a Gayngster out of homophobia, making very clear that [[EqualOpportunityEvil he views such prejudice as primitive and hypocritical]].

* The BigBad in Ringo Lam's ''Full Contact'', starring Chow Yun Fat.
* [=Gayngsters=] were an integral part of the FilmNoir trope, right from the 1941 adaptation of ''Film/TheMalteseFalcon'' to 1955's ''The Big Combo''.
* The 1931 version of ''Film/{{The Maltese Falcon|1931}}'', being from UsefulNotes/ThePreCodeEra, is even more overt with the Gayngster theme. Gutman caresses Wilmer's cheek before betraying him, and Spade calls Wilmer Gutman's "boyfriend."
* The Rock played one of these in ''Be Cool''.
* Kirill in ''Film/EasternPromises''. 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.
* PlayedForLaughs in ''Film/TheItalianJob1969'' with Camp Freddy. In fact, dressing/acting {{camp}} was kind of a GangOfHats for his group, and it should be remembered that the Boss (famously operating from a LuxuryPrisonSuite) was played by Creator/NoelCoward.
* ''Film/LayerCake'' 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 UnusualEuphemism of asking him if he is "behind with the rent".
* Harry Stark of ''Film/TheLongFirm''.
* Bernie Bernbaum and Eddie Dane from ''Film/MillersCrossing''.
* ''Film/ThePunisher2004'' 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 [[spoiler: 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.]]
* Hilly Blue (Divine) is the ''leader'' of the crime syndicate in ''Film/TroubleInMind'', slightly {{Subverted}} by the fact that he's in the TransparentCloset.
* ''Film/LuckyNumberSlevin'' 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 ''Film/BringMeTheHeadOfAlfredoGarcia'': Though not overt, the two are joined at the hip, react with disgust at the advances of two prostitutes, and Sappensly [[spoiler: loses his shit after Quill dies. Quill is also a notably phallic name]].
* Japanese director Creator/TakashiMiike is fond of this trope. Examples:
** Kakihara and his short-lived boss in ''Film/IchiTheKiller''.
** The titular ''Shinjuku Triad Society''.
** The ''Film/DeadOrAlive'' trilogy.
** ''Film/{{Gozu}}'''s [[spoiler: Minami and Ozaki]].
* Handsome Bob from ''Film/RockNRolla'' 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?
** [[spoiler: 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 ''Film/VictorVictoria'' 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 ''Film/SexyBeast.'' 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 ComingOutStory, as [[spoiler: their parents know they're engaged, but they don't know they're gangsters]].
* The Film/JamesBond movie ''Film/DiamondsAreForever'' 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 ''Film/CorkyRomano'', though he denies it for most of the film.
* Carlos in ''Quinceanera''.
* Ricki from ''Film/{{Gigli}}''. A lesbian gangster, for a change.
* Ivan and Orlando, a couple of ManlyGay henchmen from ''Film/PerriersBounty''.
* Yamada in ''Sharkskin Man And Peach Hip Girl''. He falls in love with his target.
* Harry Flowers, TheDon, in ''Film/{{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 WordOfGay) in ''Film/NorthByNorthwest''.
* 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 TheCartel in ''Film/{{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 ''Film/SmokinAces''. Vague hints of {{Gayngst}} as well.
* James Gandolfini's character in ''Film/TheMexican'' is a professional hitman/badass.
* The subtext of ''Film/LittleCaesar'' is that Edward G. Robinson has a crush on Douglas Fairbanks.
* Tha Argentine film ''PlataQuema'' (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.
* ''Film/TheMechanic2011''. The first contract killing that Bishop gives to his protégé Steve is to kill Burke, a ManlyGay rival hitman. Fortunately he HasAType -- young men from troubled backgrounds who own cute dogs. So Bishop buys a [[RidiculouslyCuteCritter chihuahua]] from the animal shelter and tells Steve to start exercising it around where Burke goes for coffee.

* Don Bruce from ''Literature/MythAdventures'', the Mob's "fairy Godfather." Not confirmed until we start getting books from Guido's viewpoint, but he's CampGay 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 ''Literature/{{Spenser}}'', ''Literature/SunnyRandall'' and ''Literature/JesseStone'' novels.
* Harry Stark in Jake Arnott's ''The Long Firm'' is intentionally something of an NoCelebritiesWereHarmed [[LondonGangster version of Ronnie Kray]].
* Turning this trope UpToEleven, in Creator/NeilGaiman's story "Keepsakes and Treasures", where there is a DiabolicalMastermind crime boss Mr. Alice who likes to have sex with attractive young men. Similar to the ''Literature/LayerCake'' example, the VillainProtagonist 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 [[BoysLove certain behavior]] which has gained association with the ancient Greeks.
* The crime lord Blood in Creator/GeneWolfe's ''Literature/BookOfTheLongSun''.
* In ''Literature/MotherlessBrooklyn'', 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 ''Literature/TheMalteseFalcon''. 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.
* Egon the Poof, a Berlin gangster in "O.G.P.U Prison" by Creator/SvenHassel that Porta and Tiny make various attempts to kill off.

[[folder:Live-Action TV]]
* ''Series/{{Caprica}}'': Sam Adama is hitman in the Tauron Mafia, he talks to his nephew [[Series/BattlestarGalactica2003 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 HappilyMarried to Larry.
* Cedric and Bob, the two very gay street toughs from ''Series/{{Seinfeld}}'' 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.
* In the ''Series/{{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.
* ''Series/{{Life On Mars|2006}}'' had at least one, giving Gene Hunt opportunity to express his "enlightened" views on homosexuality.
* In ''Series/AshesToAshes'' they discover a [=gayngster=] and Ray reacts with disbelief.
* Vito on ''Series/TheSopranos''. A straight deconstruction as the other gangsters find it disgusting, his only defender is given a hard time, [[spoiler:and he has to flee and ultimately gets whacked for it. The Sicilian mafia is not known for its tolerance]].
* ''Series/TheWire''
** 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 [[ViewerGenderConfusion 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.
* Season 3 of ''Series/{{Gotham}}'' revealed that Oswald Cobblepot, aka the Penguin, is in love with [[spoiler:Edward Nygma]].
* ''Series/NoahsArc'' had rapper Baby Gat, who had a mostly one-sided infatuation with main character Noah.
* The C4 comedy drama ''Series/{{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 CampGay traits, and HilarityEnsues 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 ''Series/MyNameIsEarl'' revolves around the titular character discovering that the respective leaders of the black and latino prison gangs are in love.
* An episode of ''Series/LieToMe'' involves [[spoiler: 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 [[spoiler: [[UnfortunateImplications abusive father]]...]]
* ''Series/TheShadowLine'' has Bob Harris and his [[CampGay incredibly camp]] boyfriend Ratallack.
* The topic of at least two ''Series/MadTV'' sketches.
** [[Series/KeyAndPeele Two gangsters]] [[https://www.youtube.com/watch?v=lPp_UrJ8aGw 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.
** [[https://www.youtube.com/watch?v=zsXMmF-ggvI 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 [[https://www.youtube.com/watch?v=RPfMjL3JmkU 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.
* One of the old gangsters in the UrbanGothic 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.
* TheMafiya member Isaak Sirko in ''{{Series/Dexter}}''. Points out to the protagonist it's NotSoDifferent from being a serial killer as they are both outcasts who have to maintain a secret dual life.
* Played for tragedy in the Series/{{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 [[spoiler:was eventually murdered by a jilted woman]].
* In the ''Series/BlakesSeven'' episode "Gambit", Krantor, leader of an OutlawTown, is strongly implied to be in a sexual relationship with his CampGay sidekick Toise.
* ''Series/JaneTheVirgin'': Rose is an international crime boss, and a lesbian.
* ''Series/OrangeIsTheNewBlack'': Alex -- former smuggler for an international drug cartel, and a lesbian -- is the most notable example, but seeing as it's a [[GirlsBehindBars show about a women's prison]], full of bi-and-lesbian criminals, there are other characters with shades of it as well.
* 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. ConsummateProfessional that he is, Lamb carries out the hit despite having real feelings for him. Lamb isn't made to feel any better by his [[AbhorrentAdmirer boss]] implying that he'd make a good ReplacementGoldfish.
* In the MusicalEpisode of ''Series/TheFlash2014'', 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.

* Music/{{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.

* Creator/TheBBC 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.

[[folder:Video Games]]
* ''VideoGame/StreetsOfRage 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.
* El Burro in the original ''[[VideoGame/GrandTheftAutoClassic 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.
* ''VideoGame/GrandTheftAutoSanAndreas'': 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 ''VideoGame/GrandTheftAutoIVTheBalladOfGayTony'' 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.
* Many games in the ''VideoGame/FireEmblem'' franchise feature two bandits, one pink, one blue that are quite clearly masochistic homosexuals.
* In the "Death on the Mississippi" mission of ''VideoGame/HitmanBloodMoney'', among the player's targets is Skip Muldoon, who runs a cruise ship business on the Mississippi river, and who is also a DepravedBisexual gang lord who is very bluntly implied to force his male ship staff to sleep with him.
* ''Franchise/MassEffect'':
** Aria T'Loak, the "Pirate Queen" of Omega in ''VideoGame/MassEffect2'', is omnisexual like all [[GreenSkinnedSpaceBabe asari]], but it's obvious she prefers the company of women upon playing through the ''Omega'' DLC of ''VideoGame/MassEffect3''.
** Captain Gavorn, a minor NonPlayerCharacter 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 ''VideoGame/MassEffect2''.
** Reyes Vidal in ''VideoGame/MassEffectAndromeda'' 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 [[spoiler:being revealed as the Charlatan, the criminal mastermind behind the Collective]].
* Sera in ''VideoGame/DragonAgeInquisition'' is an elven archer and rogue who works for the Friends of Red Jenny, a KarmicThief gang that targets nobles for valuables and mischief to help out the common people of Thedas. She is also a romance option for female [[PlayerCharacter Inquisitors]] only.
* Kanji in ''VideoGame/{{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.
* ''VideoGame/FinalFight'' 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 WordOfGod 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.
* ''Videogame/AssassinsCreedSyndicate'' has Maxwell Roth, a brutal Victorian-era LondonGangster and the mastermind of the Templar-controlled Blighters street gang. He has ''insane'' amounts of FoeYay with the game's male protagonist Jacob Frye, and WordOfGay confirmed that his overtures towards him, [[spoiler:such as giving him a TakeThatKiss before dying]], were not intended to [[FauxYay 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.
* In ''VideoGame/MafiaIII'', [[spoiler:Nicki Burke]], a high-ranking member of TheIrishMob, is gay.


[[folder:Visual Novels]]
* PlayedForLaughs in a scene of ''VisualNovel/RoseGunsDays'' Last Season. In order to infiltrate [[spoiler:the hotel where Rose is confined]], the heroes make use of their girls' charms to [[DistractedByTheSexy 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". [[FunnyMoments Though it wasn't part of the plan, they just go with it anyway.]]
* BoysLove game ''VisualNovel/LuckyDog1'' is all about this.
* Ryuuhei in ''VisualNovel/MajiDeWatashiNiKoiShinasai'' is the most typically "thuggish" of his siblings to boot. Though that might be because [[TheOneGuy he's the only male sibling]]. He also loves fighting, loves sowing chaos, and loves rape (which Yamato found out in a very ''[[SarcasmMode lovely]]'' BadEnd).

* Leon Ratterly from ''Webcomic/FriendlyHostility'' and ''Webcomic/OtherPeoplesBusiness'' works as a hitman for the Creed Corporation. He varies between [[AllGirlsWantBadBoys Bad Boy Lover]] and BastardBoyfriend towards his husband, but he's a great big teddy bear [[FamilyValuesVillain when it comes to his daughter]]. Naturally, [[DracoInLeatherPants the fandom loves him]].
* The titular character of [[Webcomic/ScandinaviaAndTheWorld Humon's]] ''Webcomic/{{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 ''Webcomic/HedoneHigh'' series is a bisexual drug dealer. [[ButNotTooBi He shows no attraction to girls, however.]] He's more interested in his best friend A.E.D.
* Pogo from in ''Webcomic/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.
* ''Webcomic/WhenSheWasBad'' has Connor Hammond, nephew to local kingpin Jakob Hammond. He isn't out to the other members of his gang.
* According to [[MsExposition Aranea]] of ''Webcomic/{{Homestuck}}'', [[GangOfHats 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. [[TooMuchInformation A graphic description of their reproductive process is as follows]].
* Basically the entire pitch of ''Webcomic/{{Griefer Belt}}''
* The webcomic ''Webcomic/{{Rechargeable}}'' is described on its website as "A queer gang in [[TheFuture 2100]] Australia".

[[folder:Web Original]]
* In ''Roleplay/TheGamersAlliance'', Galeras Matheson is one of the heads of the Matheson Crime Family and is openly gay.
* Light/Kira and Mello in ''WebVideo/DeathNoteTheAbridgedSeriesKpts4tv''.
* ''WebAnimation/FiftyPercentOff'' makes Nagisa a gangster with an obvious crush on Rei.
* [[spoiler:Alberto Falcone]] from WebVideo/TheJokerBlogs
* [[https://www.youtube.com/playlist?list=PLSZ9uKyB6R5TytxIy-9KeGiEQqF84Qb8c The Gay Cholo.]]
* Inevitable ''Literature/WhateleyUniverse'' 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.

[[folder:Western Animation]]
* Gangstalicious from ''WesternAnimation/TheBoondocks'', a gangsta rapper who is also a semi-closeted homosexual. As seen in his "[[http://www.youtube.com/watch?v=_fzuXQF_wIU 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 [[CrowningMomentOfFunny 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 [[ItMakesSenseInContext 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 ''WesternAnimation/{{Futurama}}'':
--> '''Fry:''' I know Big Vinnie ''said'' he was giving me the [[KissOfDeath kiss of death]], but I still think he was gay.
--> '''Leela:''' Did he use his tongue?
--> '''Fry:''' A little...