History Main / GayNgster

* ''WebAnimation/HazbinHotel'': 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 [[TheDreaded 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 friend Cherri Bomb asks him to.

* 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.

* ''{{Series/Whitechapel}}'': In the second season, RealLife bisexual gangster Reggie Kray is brought up (he's [[NoBisexuals described as gay]] in the series), serving as inspiration to his supposed son Jimmy Kray, who presents himself as being the same. [[spoiler:However, he may be lying as his "boyfriend" is a girl who's pretending to help him fill the role.]]

* 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]].

* Ranmaru from ''Manga/IkokuIrokoiRomantan'' is also a young {{Yakuza}} clan heir who marries his [[TheBeard beard wife]] while falling for the cruise ship's captain who hosts their lavish wedding soirée.

* ''Film/IchiTheKiller': Kakihara [[SubvertedTrope appears to be this]] for Boss Anjo, but he explains that he's rather just InLoveWithYourCarnage (the punishments Anjo gave him).

** Creator/DavidChase confirmed on the ''Talking Sopranos'' podcast that Phil Leotardo is an ArmoredClosetGay. Hence he was so angry when his son-in-law, Vito, turned out to be gay.

* ''WebAnimation/HazbinHotel'': 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 [[TheDreaded 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 UpToEleven 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 friend Cherri Bomb asks him to.

%%* ''WebAnimation/HazbinHotel'': Angel Dust was one of these in life, and he continues this occupation in Hell.

* ''Series/CriminalMinds: Evolution'': 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.

* [[{{Seme}} Asami]] is the local crime boss stalked by IntrepidReporter Takaba in the ''Manga/FinderSeries''.

* The leader of the G Boys in the manga of ''Manga/IkebukuroWestGatePark'' is all but explicitly said to be gay. None of his underlings are though.

* The second volume of ''ComicBook/OneHundredBullets'' features the obese, effeminate and openly gay Baby Maxwell in Detroit.

* 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]].

* 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.
* ''Friends/FriendsAndFamily'' 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]].

* ''Film/LuckyNumberSlevin'' featured the character called "The Fairy,'' the gay son of another gangster called "The Rabbi."

* ''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.
** Which 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.
* James Gandolfini's character in ''Film/TheMexican'' is a professional hitman/badass.

* Leonard, Creator/MartinLandau's character (according to WordOfGay) in ''Film/NorthByNorthwest''.

* Ivan and Orlando, a couple of ManlyGay henchmen from ''Film/PerriersBounty''.

* ''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.]]
* Carlos in ''Film/{{Quinceanera}}''.
* 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.

** [[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".]]
* Teddy Bass, "Mr. Black Magic" himself, from ''Film/SexyBeast.'' Teddy attends Roman-style orgies to meet wealthy and powerful men and steal from them.
* Yamada in ''Film/SharkskinManAndPeachHipGirl''. He falls in love with his target.

* Frankie Flowers, the Assassin working for TheCartel in ''Film/Traffic2000''. A cop with exclusive knowledge of this uses it to catch him at a gay bar, pretending to proposition him for sex.
* Hilly Blue (Creator/{{Divine|Actor}}) is the ''leader'' of the crime syndicate in ''Film/TroubleInMind'', slightly {{Subverted}} by the fact that he's in the TransparentCloset.

* In the Literature/ModestyBlaise 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.

* 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.

* Jesper from ''Literature/SixOfCrows'' 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.

* TheMafiya member Isaak Sirko in ''{{Series/Dexter}}''. Points out to the protagonist [[NotSoDifferentRemark 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.

* ''Series/JaneTheVirgin'': Rose is an international crime boss, and a lesbian.

* ''Series/{{Life On Mars|2006}}'' had at least one, giving Gene Hunt an opportunity to express his "enlightened" views on homosexuality.

* ''Series/NoahsArc'' had rapper Baby Gat, who had a mostly one-sided infatuation with main character Noah.

* 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.

* The C4 {{dramedy}} ''Series/ShamelessUK''

** Creator/DavidChase confirmed on the ''Talking Sopranos'' podcast that Phil Leotardo is an ArmoredClosetGay. Hence he was so angry when his son in law, Vito turned out to be gay.

* One of the old gangsters in the ''Series/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.

* ''Series/TheWire''

* A common theme on gangsta rap "diss tracks" is to question other people's sexuality.

* ''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 FoeRomanceSubtext 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.

* [[AwesomeAussie Bambi "Buck" Hughes]] in ''VideoGame/FarCry3'' is not a gangster, but he is a mercenary hired by Hoyt Volker, the leader of a [[SlaveryIsASpecialKindOfEvil massive slaver syndicate]] operating from the [[EldritchLocation Rook Islands]]. As for being gay, [[spoiler:he's keeping Jason's friend Keith as a SexSlave 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, [[ILoveTheDead he's not above "taking his meat rare"]] if he feels like it.

* 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.

* Kanji in ''VideoGame/Persona4''; he isn't in a gang, or part of an organized group of any kind beyond the Investigation Team, and he's only AmbiguouslyGay with a side of SweetOnPollyOliver, but he acts and dresses like a JapaneseDelinquent in order to cover up the shame of his enthusiastic love of traditionally-feminine things.

* Pogo, the protagonist from ''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.

* Basically the entire pitch of ''Webcomic/GrieferBelt'', which describes itself as "a {{slice of life}} series about queer criminals in the black market".

* Light/Kira and Mello in ''WebVideo/DeathNoteTheAbridgedSeriesKpts4tv''.

* ''WebAnimation/HazbinHotel'': Angel Dust was one of these in life, and he continues this occupation in Hell.

* 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.

* Gangstalicious from ''WesternAnimation/TheBoondocks'', a gangsta rapper who is also a semi-closeted homosexual. As seen in his "[[https://www.youtube.com/watch?v=_fzuXQF_wIU Homies Over Hoes]]" music video (with misogyny galore).

* Vito Spatafore 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 [[HomophobicHateCrime gets whacked for it by the homophobic Phil Leotardo and his men]]. The Sicilian mafia is not known for its tolerance]].

* ''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.

Not related to {{Gayngst}}, but overlap is possible. Also see ArmouredClosetGay, ManlyGay, which frequently overlap as well.

* ''Series/{{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.

* 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.

* 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.

* [[PlayerCharacter V]] in ''VideoGame/Cyberpunk2077'' 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 [[DeterminedWidow Wakako]] or [[BadassPreacher Padre]]). While all Vs count for this trope, the ones with a [[MultipleChoicePast 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 [[CampGay 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 [[OptionalSexualEncounter joytoy]] or starts dating [[GayOption Kerry Eurodyne or Judy Alvarez]], nothing really points to them being gay/bi.