History Main / Gayngster

* TheMafiya member Isaak Sirko in ''{{Series/Dexter}}''. Points out to the protagonist [[NotSoDifferentRemark it's not that different from 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.

* 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]].

* 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. 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.

* 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.)

* ''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.

* ''Series/PennyDreadfulCityOfAngels'': Fly Rico appears to be bi at least, given he has a casual threesome with Mateo and Rio, while also being a feared pachuco gangster.

* Male [[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]]). 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 male [[OptionalSexualEncounter joytoy]] or starts dating [[GayOption Kerry Eurodyne]], nothing really points to him being gay/bi.

* [[PlayerCharacter V]] in ''VideoGame/Cyberpunk2077'' can be played as this as same-sex romances and sexual encounters are available to the player regardless of whether or not they're playing male or female V, making V a deadly hired gun operating in the Night City underworld who just happens to be gay or bi.

* 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.

* 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.

* 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).

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.

* 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."
** King even brings it up with Squash after he comes out after all these years.

'''King:''' You were an All American. I never met a [[BadassGay meaner, rough, tough, son of a bitch football player all my life!]]\\

* Vinnie from ''Stonewall''.

* A lot of members from the mafia in ''Manga/KatekyoHitmanReborn'' have [[AmbiguouslyGay extremely questionable sexuality]]... but for a more obvious, straightforward example, Lussuria from the Varia is [[CampGay shown outright to be gay]].

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

* Tsukuyomi in ''Manga/MahouSenseiNegima'' is basically a terrorist ([[FunnyBackgroundEvent as far as Sayo is concerned]]). She's also an extreme PsychoLesbian.

* 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.

* Implied in the case of Kazuki Kasen in ''Videogame/GrandTheftAutoLiberyCityStories'', 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.

* 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]].

* 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.

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 Latinx male who dresses and acts in an unambiguously urban macho manner.

** Asami, who provides the trope image for {{Seme}}, is the local crime boss stalked by IntrepidReporter Takaba in the ''Manga/FinderSeries''.

Not related to {{Gayngst}}, but overlap is possible. May overlap with BadassGay, since [[DamnItFeelsGoodToBeAGangster crime is cool]]. Also see ArmouredClosetGay, ManlyGay

** 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 [[BadassGay explicitly homosexual]].

* 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''.

* The great Mr. 2 Bon Clay from ''Manga/OnePiece''.

* Kabu and Nirasaw from ''Manga/BiNoKyoujin'' are two StraightGay guys evolving in the highly homophobic {{Yakuza}} world.

* ''Series/InTheDark'': [[spoiler:Sam]], a fierce, no-nonsense gang enforcer, turns out to be a lesbian.