History Main / InLoveWithTheGangstersGirl

* ''Manhwa/TheTarotCafe'' has a Theatre/RomeoAndJuliet love story between the daughter of a mob boss and the son of a rival boss. Both know full well what will happen, but choose to elope. The daughter's magic pet cat is also in love with her, but no one actually knows about it. [[spoiler:The cat later dies so the daughter and her boyfriend can escape.]]

* Music/CharmingDisaster's "Showgirl" is about a New York nightclub performer who catches the eye of a police officer who's investigating the Mob... which happens to be run by her ''actual'' boyfriend. After the cop gets her mobster boyfriend sent to prison, the showgirl takes up with him, but it's unclear if she has any actual affection for either of the men or if she's just being pragmatic. One of the song's writers, Jeff Morris, has stated the song is inspired by his great-aunt, who ''actually did'' date both a mobster and a cop simultaneously in the UsefulNotes/TheRoaringTwenties.

* ''Series/{{Castle}}'' had an episode "The Blue Butterfly" involving the 50-year-old diary of a gritty private eye, a scuzzy crime boss, a gorgeous gun moll, and a diamond-encrusted butterfly. That one actually turned out very nicely.

* In ''Series/TheSopranos'', Furio gradually falls in love with Carmela Soprano after seeing her day after day while coming by to pick up Tony Soprano every morning. Furio himself is a dangerous Made Man in the Mafia, but Tony is ''the Boss''. Furio's father eventually tells him that he can either abandon his love for Carmela, or [[MurderTheHypotenuse kill Tony]]. Furio does almost go ahead with killing Tony, but backs out and flees the area instead.

* Stanley Ipkiss falls in love with Tina, the girlfriend of Dorian the gangster in ''Film/TheMask''. It results in a big showdown between the two of them, once Ipkiss gets the mask back. And it's Tina who decides she likes Stanley enough to leave Dorian, rather than Stanley trying to take Tina away.

[[caption-width-right:350:[[{{Catchphrase}} "Well, I'm boned."]]]]

* "Hide Your Heart", by Music/BonnieTyler (though written in part by Music/{{KISS}} member Paul Stanley, the band did not do a version until after Tyler).

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[[caption-width-right:350:[[{{Catchphrase}} "Well, I'm boned."]]]]

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[[folder:Anime and Manga]]

* ''Tarot Cafe'' has a Theatre/RomeoAndJuliet love story between the daughter of a mob boss and the son of a rival boss. Both know full well what will happen, but choose to elope. The daughter's magic pet cat is also in love with her, but no one actually knows about it. [[spoiler:The cat later dies so the daughter and her boyfriend can escape.]]
* This is what set up the tragic LoveTriangle between Spike, Vicious and Julia in ''Anime/CowboyBebop''. Especially tragic because Spike (who was a [[TheSyndicate Red Dragon]] member himself) and Vicious used to be the best of friends before this.
* Ian from ''Manga/ACruelGodReigns'' has a fling with a gangster's wife, although it turns out that he is possibly only a soldier.

[[folder:Film]]

* ''Film/MadDogAndGlory'' has a crime scene photographer and the bartender at the bar of a mob guy whose life he saved. Mad Dog learns that Glory is trying to pay off a personal debt to Milo, the aforementioned mob dude, and after coming up short of the money needed, he has to fight Milo, after which they make peace and Milo lets Glory go.

* An in-universe one in ''Film/SinginInTheRain''; in the FilmWithinAFilm ''The Dancing Cavaliers'', Gene Kelly's character has a DreamSequence where he imagines himself falling for Creator/CydCharisse, but ultimately losing her to her mobster boyfriend.
* Played with in ''Film/PulpFiction''; Vincent senses the rising tension between him and Mia and explicitly warns himself to avoid this trope. Not in the least because there's a rumor circulating that his boss Wallace crippled one of his other employees for screwing around with his wife, although Mia herself denies this was the reason and thinks that incident was strictly business-related.
* Stanley Ipkiss falls in love with Tina, the girlfriend of Dorian the gangster in ''Film/TheMask''. It results in a big showdown between the two of them, once Ipkiss gets the mask back. And it's Tina who decides she likes Stanley enough to leave Dorian, rather than Stanley trying to take Tina away.

* ''Film/LittleShopOfHorrors'': Seymour is in love with Audrey, who is the abused girlfriend of a sadistic dentist.

* The movie ''Film/TheMarryingMan'' starts with the protagonist sleeping with a woman who turns out to be the girlfriend of the notorious gangster "Bugsy" Siegel. Uncharacteristically the gangster is a good sport about this and rather than having the couple killed, he [[ShotgunWedding has them marry each other]].
* In the movie ''Film/WildSide'' Alex falls for Virginia who is involved with international smuggler Bruno. A LesYay version of the trope (Alex is a girl).
* This sets up the final tragedy of ''Film/ElMariachi''. Here, the title character falls in love with Domino, the girlfriend of druglord Moco. The Mariachi survives, but Domino isn't so lucky.
* Elvira, drug lord Frank Lopez's girlfriend in ''Film/{{Scarface 1983}}''. She eventually marries Tony, but the lifestyle of a druglord isn't very conducive to a happy relationship, especially since Tony disregarded her advice about [[GettingHighOnTheirOwnSupply not getting high on his own supply]], leading to Tony becoming [[SanitySlippage increasingly unstable]] and costing him his relationship with her.
* In ''Film/LostHighway'', Pete gets in deep with Alice, the gangster boss' girl.

* Emma, Harry and Paul in ''Theatre/BornYesterday''.

* In ''Film/TheFastAndTheFuriousTokyoDrift'', Sean manages this ''twice'' - first in the prologue with the school bully's girl. It doesn't end well, and he ends up on the next plane to Tokyo. There, he falls for Neela - her boyfriend, DK, is a Yakuza associate on top of his standing in the drifting community.
* ''Film/TheHitman'': Garret, an undercover cop working as a hitman for the mafia, has a fling with a mob accountant who also happens to be the mistress of the boss he's working for. He finds out. She eventually ends up with a bullet to the back of her head, Garret ends up getting sold out to the competition.
* Played with in ''Film/{{Solo}}''. Han Solo discovers his old girlfriend Qi'ra, whom he still loves, is now the right-hand woman of powerful gangster Dryden Vos, with both of them making it pretty clear Vos [[ResignationsNotAccepted won't let her go without a fight.]] It's not made explicit that there's a romantic/sexual relationship between them, though some of Vos' behavior towards Qi'ra indicates he [[ShipTease doesn't just think of her as his employee]]. Han being Han, he ignores everyone's warnings to pursue Qi'ra anyway, offering to take her away from Crimson Dawn to begin a new life. [[ForegoneConclusion It doesn't end well.]]
%%* ''Film/BlueVelvet''
* In ''Film/TheCottonClub'' Dixie Dwyer is a singer who is in love with Vera Ciciero- who happens to be Dutch Scultz's girlfriend. Dutch is not pleased.[[/folder]]

* A key element in the Creator/IainBanks story "Dead Air". The relationship and the potential consequences of ''that guy'' finding out drive much of the plot.

* In ''Series/TheSopranos'', Furio gradually falls in love with Carmela Soprano after seeing her day after day while coming by to pick up Tony Soprano every morning. Furio himself is a dangerous Made Man in the Mafia, but Tony is ''the Boss''. Furio's father eventually tells him that he can either abandon his love for Carmela, or [[MurderTheHypotenuse kill Tony]]. Furio does almost go ahead with killing Tony, but backs out and flees the area instead.

* In the ''Series/StarTrekTheNextGeneration'' episode "The Royale", Riker, Data and Worf are stuck in a virtual reality simulation of a poorly written book where the bellhop at the eponymous hotel/casino is in love with a gangster's moll. The bellhop has a gun with which to "deal" with the gangster, but the gangster kills him instead.
-->[[BondOneLiner You should have listened to me, kid.]] No woman's worth dying for. ''Killing'' for, not dying for.

* In ''Series/TwinPeaks'' Juvenile delinquent Bobby Briggs is having an affair with Shelly Johnson, the wife of the more seasoned criminal Leo Johnson
** Also [[spoiler:Sheriff Truman and Josie Packard.]]

* In "[[https://www.youtube.com/watch?v=1o1oizc4_3I El Paso]]" by Marty Robbins, both the male love interests end up dead.
-->''One night a wild young cowboy came in\\
Wild as the West Texas wind\\
Dashing and daring, a drink he was sharing\\
With wicked Felina, the girl that I loved''

* {{Inverted|Trope}} with "Copacabana" by Barry Manilow. A gangster sexually harasses the showgirl the bartender's committed to. It gets the bartender killed, and the showgirl ends up as a broken alcoholic.
* Also {{Inverted}} with Jim Croce's "Bad, Bad Leroy Brown." Leroy is used to having what he wants, sexual conquests included. He makes the mistake of trying to bed "the wife of a jealous man" and ends up having his ass kicked in full view of the neighborhood.
* "Hide Your Heart", by Bonnie Tyler (though written in part by Music/{{KISS}} member Paul Stanley, the band did not do a version until after Tyler).

* This was the plot of the 1921 musical ''Good Morning Dearie'', where it led to the first act ending with a fight scene.

* In ''VideoGame/FalloutNewVegas'', Bruce Isaac is a former lounge singer from New Reno who's in hiding after stealing money from a mob boss as well as the fact that he, in his own words, "might have... sort of... plowed his daughter. A little".

[[caption-width-right:350:[[CatchPhrase "Well, I'm boned."]]]]

->'''Ada''': I'm with you 'cause you're the only man 'round here ''not'' scared of them.\\
'''Freddie''': Oh, I'm scared of them all right.\\
'''Ada''': But you love ''me'' more than you fear ''them'', right?

[[folder: Anime and Manga]]
* A oneshot character in the ''Manga/BlackJack'' manga does this by accident, he's fallen in love with Pinoko's voice, and a coincidence makes him think the gangster's girlfriend is the one with angelic vocal cords. She isn't, and the would-be suitor makes a quick getaway.
* A story in ''Petshop of Horrors: Tokyo'' has a small-time yakuza member fall in love with his boss's girlfriend, who he knew in high school. [[spoiler:When the boss tries to frame the member for a crime, the girlfriend agrees to run away with the guy. It ends [[BitterSweetEnding not so great]]. The guy falls into the ocean and seemingly drowns so that the girl can escape. The girl is later seen telling a police officer the story, implying that she made it. It later turns out that the yakuza member was turned into a dog and taken in by one of D's purebreds.]]

* This is what set up the tragic LoveTriangle between Spike, Vicious and Julia from ''Anime/CowboyBebop''. Especially tragic because Spike (who was a Red Dragon member himself) and Vicious used to be the best of friends before this.

[[folder: Film]]

[[folder: Literature ]]

[[folder: Live-Action TV]]

[[folder: Music]]

-->One night a wild young cowboy came in.
-->Wild as the West Texas wind.
-->Dashing and daring, a drink he was sharing
-->With wicked Felina, the girl that I loved.

-->''Then all of a sudden the music changed, and everyone just held their pulse''
-->''But it felt like your life had been robbed from you, and everything that you held close''
-->''That someone had stolen the woman you loved, and that her love was a devil's lie''
-->''That your heart was gone, and the best thing that you could do was crawl away and die''
-->''It's the painful cry of a man's despair, deep down in his bones''
-->''"I guess misery enjoys company", said big bad Solomon Jones''
* {{Inverted}} with "Copacabana" by Barry Manilow. A gangster sexually harasses the showgirl the bartender's committed to. It gets the bartender killed, and the showgirl ends up as a broken alcoholic.

* {{Downplayed}} and PlayedForLaughs in Jay and the Americans "Come a Little Bit Closer." The narrator is in a bar and the girlfriend of "Bad Man Jose" flirts with him. Attracted, he has a dance and kisses her...but then Jose shows up and he jumps out the window to avoid Jose's wrath. The girlfriend, without skipping a beat, goes and uses the same come-on lines on Jose she was using on him.

[[folder: Newspaper Comics]]
* ''ComicStrip/{{Luann}}''. Luann's brother Brad fell in love with his next-door neighbor Toni Daytona. Unfortunately, she turned out to have an emotionally abusive and dishonest boyfriend named Dirk, who was extremely muscular and could have broken Brad in half without trying.

[[folder: Theatre]]

[[folder: Video Games]]

* In ''Videogame/FalloutNewVegas'', Bruce Isaac is a former lounge singer from New Reno who's in hiding after stealing money from a mob boss as well as the fact that he, in his own words, "might have... sort of... plowed his daughter. A little".

[[folder: Western Animation]]

* In the third episode of ''Series/QuantumLeap'', Ben discovers that his leapee, a boxer named Danny, is in a secret relationship with the girlfriend of his boxing opponent.

* In ''Series/{{TwinPeaks}}'' Juvenile delinquent Bobby Briggs is having an affair with Shelly Johnson, the wife of the more seasoned criminal Leo Johnson

* Furio with Carmela in ''Series/TheSopranos''. Subverted in that Furio is a gangster too, but Tony is ''the boss''.

* ''Film/{{Bound 1996}}'' is a GenderFlip version, or half of one. A lesbian ex-con falls in love with a mafioso's girl, and the girl reciprocates. Then they hatch a scheme to get rid off him, which ends up backfiring on them when he proves to be far more resourceful than either of them anticipated.

* In ''Film/TheCottonClub'' Dixie Dwyer is a singer who is in love with Vera Ciciero- who happens to Dutch Scultz's girlfriend. Dutch is not pleased.[[/folder]]

-->One night a wild young cowboy came in. Wild as the West Texas wind.
-->Dashing and daring, a drink he was sharing with wicked Feleena, the girl that I love.

* In the ''Series/{{Seinfeld}}'' episode "The Friar's Club," Kramer dates a girl who refuses to be seen with him in public. It turns out to be for this reason. The real danger is (unintentionally) from her, however; when Kramer falls heavily asleep in mid-makeout (having been recently attempting polyphasic sleep, which left him seriously sleep-deprived) and she thinks he's dead, she calls some friends to dump the "body" into the Hudson River rather than have her boyfriend find out that she was cheating. Kramer escapes but never finds out what was really going on, assuming she tried to have him killed [[IfICantHaveYou to keep anyone else from having him]].

* In the ''Series/{{Seinfeld}}'' episode "The Friar's Club," Kramer dates a girl who refuses to be seen with him in public. It turns out to be for this reason. The real danger is (unintentionally) from her, however; when Kramer falls heavily asleep in mid-makeout (having been recently attempting polyphasic sleep, which left him seriously sleep-deprived) and she thinks he's dead, she calls some friends to put him in a sack and dump him into the Hudson River rather than have her boyfriend find out that she was cheating. Kramer escapes but never finds out what was really going on, assuming she tried to have him killed [[IfICantHaveYou to keep anyone else from having him]].

* In the ''Series/{{Seinfeld}}'' episode "The Friar's Club," Kramer dates a girl who refuses to be seen with him in public. It turns out to be for this reason, and when Kramer falls heavily asleep in mid-makeout (having been recently attempting polyphasic sleep, which left him seriously sleep-deprived) and she thinks he's dead, she calls some friends to put him in a sack and dump him into the Hudson River rather than have her boyfriend find out that she was cheating on him.

* An in-universe one in ''Film/SinginInTheRain''; in the FilmWithinAFilm ''The Dancing Cavaliers'', Gene Kelly's character has a DreamSequence where he imagines himself falling for Cyd Charisse, but ultimately losing her to her mobster boyfriend.

*

[[/folder]]