History Main / Gayngster

* 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.
* Hilly Blue (Divine) is the ''leader'' of the crime syndicate in ''Film/TroubleInMind'', slightly {{Subverted}} by the fact that he's in the TransparentCloset.

* Tha Argentine film ''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.

%%* Vinnie from ''Film/{{Stonewall}}''.

* ''Manhwa/WetSand'': 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.

* 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.

* Chris Penn's character in ''Film/CorkyRomano'', though he denies it for most of the film.

%* Not to mention the shoujo classic ''Manga/BananaFish''.

* Many games in the ''VideoGame/FireEmblem'' franchise feature two bandits, one pink, one blue that are quite clearly masochistic homosexuals.

* ''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.
* ''Series/InTheDark'': Sam, a fierce, no-nonsense gang enforcer, turns out to be a lesbian.
* ''{{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.]]
* Dinsdale Piranha in the ''[[Series/MontyPythonsFlyingCircus Monty Python]]'' episode "[[Recap/MontyPythonsFlyingCircusS2E1 Face the Press]]," being a Ronnie Kray parody, is a brutal LondonGangster who nails people's heads to the floor, has a "warm interest" in boys' clubs, sailors' homes, and [[TakeThat the Household Cavalry]], and dated a DragQueen.
* ''Series/PennyDreadfulCityOfAngels'': 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.
* ''Series/BigSky'': The criminal duo Paul and Snail in "All Kinds of Snakes" are a couple.
* ''Series/LawAndOrderOrganizedCrime'':
** Nova is a Black gangster who's also a lesbian. [[spoiler: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.
* It's heavily implied that Gus Fring of ''Series/BreakingBad'' and ''Series/BetterCallSaul'' 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''.
* ''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.

* ''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.

* Many games in the ''VideoGame/FireEmblem'' franchise feature two bandits, one pink, one blue that are quite clearly masochistic homosexuals.

* 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.

* ''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 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.
** 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.
* [[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.
* [[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.
** [[AmoralAfrikaner Hoyt Volker]] himself briefly plays this for FauxYay BlackComedy. After [[spoiler: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.

* 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". Though it wasn't part of the plan, they just go with it anyway.

* 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.

* 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.
** Considering that the majority of the Underground are descendants of a PenalColony, 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.
* ''Webcomic/WhenSheWasBad'' has Connor Hammond, nephew to local kingpin Jakob Hammond. He isn't out to the other members of his gang.

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

* Tielo and Fergal of ''Webcomic/{{Otherworldly}}''. Members of the Unseelie Mob (TheFairFolk version of organized crime), and also fiancés.

* In ''Roleplay/TheGamersAlliance'', Galeras Matheson is one of the heads of the Matheson Crime Family and is openly gay.

* [[spoiler:Alberto Falcone]] from WebVideo/TheJokerBlogs

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

* 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 - and possibly about his own sexuality.
* 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.
** 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.
* The protagonist of ''Film/{{Moonlight|2016}}'' 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.
* In ''Film/ColdPursuit'', two of Viking's crew, [[spoiler:Mustang and Dexter]], are a couple and are hiding it from the rest of the gang.
* ''Film/InOrderOfDisappearance'': 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.
* In ''Film/BirdsOfPrey2020'', 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.
* ''Film/TenDeadMen'': 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.
* Irish coming-of-age film ''Cowboys and Angels'' features [[spoiler: 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.]]
* In ''Film/HighHeelsAndLowLifes'', Mason's boss is a Kerrigan, an old-school gay LondonGangster with a veneer of civilisation (played by Creator/MichaelGambon). Behind his back, Mason refers to him as "the old poof", but Kerrigan is the one person that hard man Mason is scared of.
* ''Film/TheKillingGene'': Daniel is a gangster who, along with the rest of the gang, raped Jean and murdered her mother. He's also sleeping with [[spoiler:and informing for Eddie, a police officer who's investigating the gang, suggesting he's at least bisexual.]]

* 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 Creator/RobertBParker's ''Literature/{{Spenser}}'', ''Literature/SunnyRandall'' and ''Literature/JesseStone'' novels.

* In Creator/NeilGaiman's story "Keepsakes and Treasures", 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.

* 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.

* 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 ''Series/AshesToAshes2008'' they discover a [=gayngster=] and Ray reacts with disbelief.
* 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/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]].

* ''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/MadTV1995'' 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."

* 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.
* 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.

* 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]].



* Eighties Irish thriller ''The Courier'' (not to be confused with the [[Film/TheCourier2021 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).
* 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''.

* This trope is a staple of the BoysLoveGenre in general when the story focuses on {{Yakuza}} society, for example:
** Nirasawa from ''Manga/BiNoKyoujin'' is a StraightGay {{Bishonen}} 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 BattleButler.
** Similarly ''Manga/{{Kizuna}}'' also focuses on the {{Yakuza}} setting, but in a rather less grim and more romanticized way.
** Kano from ''Manga/OkaneGaNai'' is also an example of this trope, of the LoanShark 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.
** [[{{Seme}} Asami]] is the local crime boss stalked by IntrepidReporter Takaba in the ''Manga/FinderSeries''.
** 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.
** Yashiro from ''Manga/TwitteringBirdsNeverFly'' 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.
* A lot of members from the mafia in ''Manga/Reborn2004'' have [[AmbiguouslyGay extremely questionable sexuality]]... but for a more obvious, straightforward 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.
%%* Not to mention the shoujo classic ''Manga/BananaFish''.
* Buppa, one of the mob bosses in ''Manga/{{Tokyo Tribe}}s'', is a FatBastard DepravedBisexual who rapes boys so hard they explode. Really.
* Tsukuyomi in ''Manga/NegimaMagisterNegiMagi'' is basically a terrorist ([[FunnyBackgroundEvent as far as Sayo is concerned]]). She's also an extreme PsychoLesbian.
* Minor villains Squalo and Tiziano from ''Manga/JoJosBizarreAdventureGoldenWind'', they are dedicated enough to each other than [[spoiler:Tiziano doesn't hesitate to [[TakingTheBullet 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 CampGay due to their really weird clothes, but don't really show any attraction to the same sex. [[UsefulNotes/{{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'' is a rare CampGay version of this trope.

* ''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/ShadowStar'', 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]].

* 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.

* 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.

* ''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=].

* 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.

* 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.

[[folder:Film]]
* 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/{{The Maltese Falcon|1941}}'' 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."
* ''Film/{{Hammett}}'', a 1982 fictionalized account of Creator/DashiellHammett's life before he wrote ''Literature/TheMalteseFalcon'', is also quite overt about the Gutman/Wilmer {{expy}}s English Eddie Hagedorn and "The Punk."
* Creator/DwayneJohnson played one of these in ''Film/BeCool''.

* 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 ''Film/GangsterNo1'' 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]].

%%* Vinnie from ''Stonewall''.

* 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.]]

* ''Film/TheKillingGene'': Daniel is a gangster who, along with the rest of the gang, raped Jean and murdered her mother. He's also sleeping with [[spoiler:and informing for Eddie, a police officer who's investigating the gang.]]

* The topic of at least two ''Series/MadTV'' sketches.

* 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]].

* 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.
** If the player waits long enough, OG Loc ''will'' kill the boyfriend himself.
* Implied in the case of Kazuki Kasen in ''VideoGame/GrandTheftAutoLibertyCityStories'', 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 ''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.

* ''Film/Hammett'', a 1982 fictionalized account of Creator/DashiellHammett's life before he wrote ''Literature/TheMalteseFalcon'', is also quite overt about the Gutman/Wilmer {{expy}}s English Eddie Hagedorn and "The Punk."

* The Rock played one of these in ''Be Cool''.

* 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]].

* It's heavily implied that Gus Fring of ''Series/BreakingBad'' and ''Series/BetterCallSaul'' was more than friends with his first meth cook, Max. Nothing's ever confirmed, but Hector Salamanca makes a disparaging comment about it.

* Kanji in ''VideoGame/Persona4''; 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.

* Minor villains Squalo and Tiziano from ''Manga/JoJosBizarreAdventureGoldenWind'', they are dedicated enough to each other than [[spoiler:Tiziano doesn't hesitate to [[TakingTheBullet 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 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.

* Minor villains Squalo and Tiziano from ''Manga/JojosBizarreAdventureVentoAureo'', they are dedicated enough to each other than [[spoiler:Tiziano doesn't hesitate to [[TakingTheBullet 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 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.

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

* 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.

* Eighties Irish thriller ''The Courier'' (not to be confused with the [[Film/TheCourier 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 [[Gayngst 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).