History Main / DamnItFeelsGoodToBeAGangster

The critic Robert Warshow wrote a famous essay called ''The Gangster as TragicHero'', in which he posited that gangsters like those in ''Film/{{Scarface|1932}}'' are Americanized versions of Greek or Shakespearian tragic heroes, dark mirrors of UsefulNotes/TheAmericanDream, or the "great no" to the American promise of success. He argued that they were a counter to the films made in UsefulNotes/TheGoldenAgeOfHollywood, and were a form of WishFulfillment for working-class audiences with their RagsToRiches stories and charismatic, tragic characters. Even when ExecutiveMeddling had the bad guys getting punished, the filmmakers and actors conspired to give the villain protagonists a memorable [[DyingMomentOfAwesome death scene]] that made audiences CryForTheDevil, similar to classic tragic heroes and villains. This essay made a big impact on the likes of Creator/FrancisFordCoppola and Creator/MartinScorsese and informed their GenreDeconstruction in ''Film/TheGodfather'' and ''Film/{{Goodfellas}}''; in the case of ''The Godfather'' it was essentially an UnbuiltTrope.

* ''Film/{{Goodfellas}}'' is arguably the purest and most famous example of all time, despite also being known for its more "gritty" take on TheMafia. Since it's based on a true story, it's largely a straight example for the first two hours (with a few scenes showing the dark side, like being arrested -- but even ''then'' it's an idyllic stay in jail), and then a ruthless, horrific subversion for the last hour as people get whacked left and right...But the main character, in-universe and in RealLife, [[AesopAmnesia still wanted to be a gangster even after all that.]]

* ''Series/{{Community}}'': As far back as Abed can remember in "[[Recap/CommunityS1E21ContemporaryAmericanPoultry Contemporary American Poultry]]" (a WholePlotReference to ''Goodfellas''), he always wanted to be in a Mafia movie.

* ''Series/TheWire'': Omar. [[{{Gayngster}} Except the "irresistible to women" part]].

* The pirate equivalent in ''Franchise/PiratesOfTheCaribbean''. The pirate lifestyle in general is depicted to be a romanticized badass madcap {{swashbuckler}} life of adventure where you get to wear awesome clothes, bed a different salty wench in every port, go through fortunes of doubloons like water, outwit mythical beings, stick it to the man, and most of all ''have the freedom to determine your life's course.''
* ''Film/TheGodfather'' is a general subversion of this trope. The mafia lifestyle, for those at the top, is very glamorous, with Vito holding court from a palatial estate filled with minions. However, as the film goes on, it becomes increasingly clear that the family business is filled with misery and tragedy. The Corleone family gets ripped apart over the course of the series, and Michael never seems to enjoy being a crime lord.
* ''Film/{{Scarface 1932}}'' deconstructs this. Also applies to the ''Film/{{Scarface 1983}}'' remake with Creator/AlPacino, which remains hugely popular to this day with the MisaimedFandom.

* ''Film/{{Gomorrah}}'' is one of the most scathing subversions ever of this trope, as each one of its five stories is a repudiation of TheMafia, showing how unglamorously evil, cowardly, and unfair it can be, essentially parasites sucking the life out of the Scampia and Secondigliano regions in Italy. Bonus points for the story with the two kids who believe in this trope and think they're budding badasses in a ComingOfAgeStory, only to be [[WrongGenreSavvy brutally disabused of it]].
* ''Film/{{Goodfellas}}'' is arguably the purest and most famous example of all time, despite also being known for its more "gritty" take on TheMafia. Since it's based on a true story, it's largely a straight example for the first two hours (with a few scenes showing the dark side, like being arrested -- but even ''then'' it's an idyllic stay in jail), and then a ruthless, horrific subversion for the last hour as people get whacked left and right...But the main character, in-universe and in RealLife, [[AesopAmnesia still wanted to be a gangster even after all that.]]

* Another Scorsese film ''Film/TheIrishman'' is a very ruthless {{Deconstruction}} of this trope to the point where the main protagonist Frank Sheeran has lost everything and everybody he loves dearly.
* ''Film/ReservoirDogs'' and ''Film/PulpFiction'' are often considered deconstructions of this trope, [[Creator/QuentinTarantino but they're still ridiculously cool]].
* Creator/GuyRitchie movies in general, i.e. ''Film/LockStockAndTwoSmokingBarrels'', ''Film/{{Snatch}}'', ''Film/RockNRolla''.

* ''Film/PublicEnemies''
** Dillinger and his squad are filthy rich, help out the common man caught in a financial bind, can woo and bed a different woman every night if they wish, and are generally seen having the times of their lives when they're not dealing with being chased by police or committing bank robbery -- much of which is TruthInTelevision given the real Dillinger's courtesies during at least one of his bank robberies (where he gave a shivering woman his coat). Baby Face Nelson on the other hand was the opposite of Dillinger.
** Likewise, Melvin Purvis, his team, and J. Edgar Hoover are depicted as asexual, aloof, and mechanically devoted to the task of catching crooks, often times descending into wanton destruction of civilian property and civilians.
** The same could be said for those who traveled in close circles that involved Dillinger or Alvin Karpis.
* There's a bit of a cottage industry in averting this trope for more serious works.
** ''Film/EasternPromises'', [[http://pandagon.blogsome.com/2007/10/01/6113/ as thoroughly described by Amanda Marcotte here.]] It's made excruciatingly clear that the gangsters' power rests on an endless heap of raped, abused, and eventually murdered women. Two of the gangsters given character development are a monster and an ineffectual drunk; the one ambiguously nice badass [[spoiler:turns out to be TheMole]].
* ''Film/AngelsWithDirtyFaces'': James Cagney as Rocky Sullivan; he just makes being a gangster look so cool. This is actually discussed and deconstructed through the film. Sullivan becomes something of a hero to the neighborhood kids with his gangster lifestyle, but all it brings him is paranoia, pain, and [[spoiler: death row at the end.]] A huge part of the end of the film is his best friend begging him to destroy his own legend and be remembered as a coward so the kids won't follow in those footsteps.

* ''Film/AmericanGangster'' subverts this with Frank Lucas being a believer in dressing conservatively both as a way to avoid the attention of the law and as a sign of strength. In fact, the only time he disregards this personal standard with a flashy Chinchilla fur coat and hat for a night out turns out to be the biggest mistake of his life as Detective Richie Roberts notice this fancy-dressed newcomer in the New York crime circles and they begin investigate him.

* In ''Film/BugsyMalone'', the song [[VillainSong "Bad Guys"]] is sung by most of Fat Sam's gang -- all about how brilliant it is to be gangsters. Dandy Dan's gang don't have a song, but they all probably apply as well.
* ''Film/SinCity'' plays with this. The mafia is seen as living a rich and powerful lifestyle but many of them get killed off en masse by the heroes. Then again, they remain in power despite the heroes' efforts, usually. [[spoiler: And in some cases, they outlive the heroes but usually at great cost.]]
* Averted in ''Film/AlphaDog''. Right from the start, it's clear that these are a bunch of loser assholes that only an idiot would want to emulate.
* Deconstructed in ''Film/KingOfNewYork''. Jimmy relishes the gangster lifestyle and its perks but is completely unprepared for the harsh side of it. Frank clearly derives no pleasure from it, detests many of the men in the trade, and suffers from deep self-loathing over the things he's done to gain power.

* In ''Film/AtlanticCity'', Lou is an elderly two-bit hood who collects for a penny-ante numbers racket, but he likes to reminisce about his days as a mob enforcer and hitman. It turns out he was [[MilesGloriosus making most of it up]]. When he winds up with a stash of cocaine, he has a lot of fun spending the proceeds on snappy suits and [[MayDecemberRomance his much younger sexy neighbor]]. But when he finally winds up having to kill two real gangsters, he is thrilled to death, gleefully bragging to a random hotel clerk about how he just committed a double murder.
* In the first half of ''{{Film/Fresh}}'', this is the attitude of the titular character. Despite being 12 years old, he already runs drugs for two local gangs, and he brags to his schoolyard crush about how he's going to become a bigshot gangster. She is killed before his eyes when the PsychopathicManchild gangster Jake starts a shootout because he was losing at basketball. It's then he realizes, as the audience probably did well before that point, that the trope is very much subverted. The rest of the movie involves Fresh clawing his way out of the crime-riddled ghetto he lives in. Over the corpses of the gangsters.
* ''Film/TheActOfKilling'' deconstructs this -- the gangsters are perfectly happy with their lifestyle, and society celebrates them, but the focus is on the atrocities they have committed.
* Subverted in ''{{Film/The Limey}}''. "I embrace this lifestyle," insists Stacy the Hitman, [[spoiler:only to be knocked off well before the credits roll.]]
* ''Film/ABronxTale'': C thinks this is true after hanging out with Sonny and getting to see all the perks. However, his father Lorenzo and Sonny himself try to convince him otherwise. Lorenzo points out that everyone in the neighborhood treats him great because they fear him and he can't trust anybody and Sonny tells C that [[IDidWhatIHadToDo he just did what he had to do]] and C would be better off going to college.
* ''Film/AmericanAnimals'': Early scenes emphasize how much fun Spencer and Warren are having being criminals and planning their heist. One scene has them rob a meat locker and drive away while exultantly singing along to Johnny Thunder's "I'm Alive."

* In ''Film/BrokenArrow1996'', Deakins has been planning to break bad for some time, and when he does, he's in his element to the point where it's hard to believe he was ever one of the good guys. When his ex-partner Hale tells him he's crazy, he simply replies "I know! Ain't it cool?"

* In the 1989 film WesternAnimation/AllDogsGoToHeaven, the protagonist, Charlie, is a pretty prominent mafioso who's unfortunately whacked by a business associate. When he returns to Earth, Charlie makes a fortune on gambling and builds his dream casino. The film doesn't shy away from glamorizing his life.

* ''Manga/{{Gangsta}}.'' is all about this. The coolest and most sympathetic characters are either mafioso, prostitutes, crooked cops, or AxCrazy DifferentlyPoweredIndividuals.

* ''Film/{{Gomorrah}}" is one of the most scathing subversions ever of this trope, as each one of its five stories is a repudiation of TheMafia, showing how unglamorously evil, cowardly, and unfair it can be, essentially parasites sucking the life out of the Scampia and Secondigliano regions in Italy. Bonus points for the story with the two kids who believe in this trope and think they're budding badasses in a ComingOfAgeStory, only to be [[WrongGenreSavvy brutally disabused of it]].

* Film/{{Gomorrah}}" is one of the most scathing subversions ever of this trope, as each one of its five stories is a repudiation of TheMafia, showing how unglamorously evil, cowardly, and unfair it can be, essentially parasites sucking the life out of the Scampia and Secondigliano regions in Italy. Bonus points for the story with the two kids who believe in this trope and think they're budding badasses in a ComingOfAgeStory, only to be [[WrongGenreSavvy brutally disabused of it]].

* Film/{{Gomorrah}}" is one of the most scathing subversions ever of this trope, as each one of its five stories is a repudiation of TheMafia, showing how unglamorously evil, cowardly, and unfair it can be, essentially parasites sucking the life out of the Scampia and Secondigliano regions in Italy.

** Although ''VideoGame/MafiaII'' just simply went down the route of having two-thirds of the game glamorize being a gangster before having everything fall apart for the protagonist in the last act. However, it comes off as a subversion for much of the game, as much of the protagonist's activities in the mafia pretty much come off as yet another dead-end-job that's much riskier - there's no real advancement, no path to the top, and it all ends up being not remotely worth the effort.

* {{Deconstructed}} in the ''VideoGame/{{Yakuza}}'' series. When the first game begins, Kiryu is on his way to being a made man; but after TakingTheHeat for a murder his best friend committed, and the chaotic events that followed, he decides to leave his life of crime behind to be a surrogate father to Haruka, only reluctantly returning to the criminal underworld of Japan to help his friends. Majima, meanwhile, seems to exemplify this as Kiryu's polar opposite, gleefully taking in the yakuza lifestyle and all of the violence it entails. As shown in ''VideoGame/Yakuza0'', however, he had to make quite a few sacrifices to attain his position.
** In a flashback in ''0'' it is shown that Kiryu firmly believed this as a teenager. His foster father, who knew better than most what the lifestyle meant in terms of sacrifices, losses, and traumas from experience, did his best to dissuade him, but it didn't take. Kiryu spent most of his life learning how right his dad had been the hard way.

* Subverted in ''VideoGame/SleepingDogs'', life in the Sun On Yee is at first idolized by the likes of Jackie Ma and Wei's friends in the gang. However, it causes the once-childhood friends Dogeyes and Winston to violently drift apart ending with [[spoiler: a massacre at Winston's wedding where nobody was spared, including Winston's wife to be Peggy and Dogeyes being violently chopped by Winston's vengeful mother who feeds Dogeyes the remains of Ratface]]. As a succession crisis forces new members like Jackie to be induced, the harsh realities sink for everyone as the ongoing conflicts lead from one massacre to another with civilians constantly caught in the crossfire and people like Jackie unaccustomed to murdering someone. [[spoiler: When Uncle Po dies, Big Smile Lee purges many competitors to his position as the head and has Jackie Ma violently tortured to death shortly after a TraumaCongaLine and Wei barely survives]].

When the cool criminal is the lead character, they're probably a VillainProtagonist or AntiHero. [[VillainWithGoodPublicity Their PR may be helped]] by only doing crimes against{{Asshole Victim}}s, as in a KarmicThief or SympatheticMurderer.

When the cool criminal is the lead character, they're probably a VillainProtagonist or AntiHero. [[VillainWithGoodPublicity Their PR may be helped]] by only doing crimes against a {{Asshole Victim}}s, as in a KarmicThief or SympatheticMurderer.