[[quoteright:350:[[VideoGame/MafiaII http://static.tvtropes.org/pmwiki/pub/images/mafia2screenshot_201.jpg]]]]
[[caption-width-right:350:[[{{Anvilicious}} Doesn't work out that well for him at the end.]]]]

->''"As far back as I can remember, I always wanted to be a gangster."''
-->-- '''Henry Hill''', ''Film/GoodFellas''

Criminals are ''[[EvilIsCool cool]]''. It might be a [[FamilyUnfriendlyAesop terrible thing to say]], but it's true. One of the most enduring images in modern fiction is that of the glamorous gangster -- a streetwise, SelfMadeMan who's rich, powerful, badass, [[AllGirlsWantBadBoys irresistible to women]], [[BadassInANiceSuit fashionable]], and [[TheSociopath unfettered by conventional morality]]. In short, a perfect EscapistCharacter for times when [[GoodIsBoring being a good guy is just too dull]].

Violence might be abhorrent in RealLife, but on the big screen it can be just another way to get the audience's adrenaline flowing, [[TropesAreNotBad and there's nothing wrong with that]]. Besides, in fiction, it doesn't matter how many [[KickTheDog dogs you kick]] as long as you [[RuleOfCool look really cool]] when you do it.

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 film-makers 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.

This trope was widely popularized in the US during TheRoaringTwenties, when Prohibition made organized crime big business and the gangster became one of the iconic figures of the era; and TheGreatDepression, where bank robbers were seen as striking at the greedy and foolish banks that got the country into this mess. Of course, it has [[OlderThanTheyThink roots much further back in history]] -- the popularity of outlaws like Jesse James and Billy the Kid in the American frontier era certainly counts, and even as far back as Robin Hood it was cool to steal. However, modern works are more likely to subvert or deconstruct this trope as play it straight. Indeed, the [[{{Tragedy}} "rise and fall" narrative]] has become such an integral part of the gangster genre that [[DeadHorseTrope it now makes straight examples of this trope nigh impossible]].

SubTrope of EvilIsCool and closely related to DoNotDoThisCoolThing. A direct opposite of BeingEvilSucks. See also NeighborhoodFriendlyGangsters and DracoInLeatherPants. If the criminals aren't ever shown actually doing anything, well, ''criminal'', they're ThePiratesWhoDontDoAnything. Criminals who believe in this point of view may opt to be JustAGangster and turn down chances to leave their criminal life behind.



[[folder:Anime and Manga]]
* Mello from ''Manga/DeathNote''. He ''took over the mafia,'' and spent most of his time in it wearing leather, eating [[TrademarkFavoriteFood chocolate]], lounging on a garish zebra-print sofa (or sometimes a decadent leather chair), and making MagnificentBastard Light and TeenGenius Near look like idiots.
* ''LightNovel/{{Baccano}}'': Even the most innocent and endearing characters in the series have connections to either the Mafia or Camorra.
** Firo actually invokes this in the LightNovels, citing one of the reasons for joining the Camorra was "to be like the Italians who appeared in those movies and stories."
** Being a gangster feels so damn good that even omnipotent {{Eldritch Abomination}}s want in on it. Just ask [[spoiler:Ronnie]].
* Mostly avoided in the ''VideoGame/{{Gungrave}}'' anime: While Big Daddy's mafia is quite stylish and honorable, and there are some scenes with cool cars and houses, it is never a major point of the series. Harry, with his fast cars, white suits, and beautiful women, comes closest to this trope... though of course, it doesn't last.
* Subverted in ''Manga/BlackLagoon'': Although The Lagoon Company, and Balalaika's [[TheMafiya Hotel Moscow]] branch initially appear to be playing this straight the series makes it ''very'' obvious that these are ''not'' happy people. Balalaika and her men were more or less forced into a life of crime after they were screwed over by their own government.
* ''Manga/JoJosBizarreAdventure'': In Giorno's case, It feels good to be a Gang''star''!
* ''Manga/{{Gangsta}}.'' is all about this. The coolest and most sympathetic characters are either mafioso, prostitutes, crooked cops, or AxCrazy DifferentlyPoweredIndividuals.
* ''Manga/BlackJoke'': All central characters are gangsters, and the crime world is depicted as very exciting and luxurious.
* ''Manga/KatekyoHitmanReborn'' and its mafioso families who are very badass. There are ten of 'em and ItRunsInTheFamily.
* ''Manga/BungouStrayDogs'': The Guild are a bunch of international people [[NamedAfterSomebodyFamous named after real life authors]] who have awesome powers, live swanky lifestyles and kick tonnes of ass. However, averted by Kyouka, who once was a pawn of the port mafia and at present still lives in fear of them despite her HeelFaceTurn.
* ''Manga/ShouwaGenrokuRakugoShinjuu'' has Kyoji (reformed criminal who wants to pursue rakugo, so an aversion) and his boss (played straight). The boss tries to preach this lifestyle, only to get trumped by Kyoji's performance of Dekigokoro, about a boss and the underling who tries to prove himself to him.

[[folder:Comic Books]]
* In the ''[[ComicBook/LukeCage Power Man]] and ComicBook/IronFist'' (2015) series, [[spoiler:[[ComicBook/{{Runaways}} Alex Wilder]]]] says this word for word after viciously taking over one of the gangs in Harlem.

[[folder:Films -- Live-Action]]
* 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'' and its sequels apply the trope to some, but not all, of the characters. Most of the lives of the gangsters are glamorous, with Vito Corleone's reign in particular being idyllic. However, the hardships end up destroying the happiness of Michael's family and lead to the violent murders of Sonny and Fredo.
** Even the latter part of Vito's reign (especially when the other families turned against him) breaks down the glamor of Mafia life. The whole series is a complete deconstruction of the trope, with even Michael seeking redemption he knows he can never get at the end of his life.
* ''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.
* Arthur Penn's heavily fictionalized portrayal of the title bank robbers in ''Film/BonnieAndClyde'', one of the original "New Hollywood" films, is a very influential example.
* ''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....But the main character, in-universe and in RealLife, [[AesopAmnesia still wanted to be a gangster even after all that.]]
** Creator/MartinScorsese being TheMovieBuff knew this trope well and deliberately subverted it with this film, insisting that audience look at it from the inside and sort [[GrayAndGrayMorality their own moral alignment themselves]].
* ''Film/{{Casino}}'', with Robert [=DeNiro=].
* ''Film/ReservoirDogs'' and ''Film/PulpFiction'' are often considered {{Deconstruction}}s 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/FightClub'' made it look so cool to be in such a club that it was pretty much inevitable that [[http://en.wikipedia.org/wiki/Fight_Club_(film)#Cultural_impact some people started their own]].
* ''Film/PublicEnemies'' -- Dillinger and his squad are filthy rich, helps 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 the ReverseMole]].
* ''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.
** In fact, [[TypeCasting most movies]] with Creator/JamesCagney qualify.
* Daniel Day Lewis' show-stealing performance as Bill the Butcher in ''Film/GangsOfNewYork'' is made of this trope.
* ''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 fur coat and hat for a night out turns out to be the biggest mistake of his life as the cops notice this fancy dressed newcomer in the New York crime circles and they investigate him.
* The film version of ''Film/LayerCake'' subverted this trope while deconstructing it. At first the protagonist makes dealing in cocaine look like easy, stylish money with and excellent pension plan. By the end, he's been through hell and back just trying to retire into obscurity, and the audience is shown via the medium of BlackComedy just how lame the criminal underworld can be.
* 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.
* At the end of ''Film/JohnnyDangerously'', Johnny admonishes the audience that "Crime doesn't pay" -- and then when his limo pulls up and two dames drape themselves over his arms, he admits, "Well, it pays a little."
-->'''From the theme song by Music/WeirdAlYankovic:''' "If money can't buy happiness, I guess I'll have to rent it!"
* 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. Said crush is killed before his eyes when the PsychoticManchild gangster Jake start 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 in 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.

* Zett Nilric in ''Literature/StarTrekVanguard'', who is elegant, mannered and sharply dressed to a fault, an expert swordsman, and definitely has a certain flair. Another example from the ''Franchise/StarTrekNovelVerse'' is Ihasz, who shows up in [[Literature/StarTrekATimeTo ''A Time To Heal'']] and [[Literature/StarTrekArticlesOfTheFederation ''Articles of the Federation'']].
* ''Literature/{{Dragaera}}'' series protagonist Vlad Taltos. Bit of a deconstruction in the later books of the time line, but ''Taltos'' in particular is made of this.
* [[Franchise/ConanTheBarbarian Conan]] spends much of his time (and started his career) as a thief, but moves on to bigger and better things including mercenary soldier, mercenary general, and eventually king of Aquilonia. The original stories (and the 1980 movie treatment) note how much more honorable Conan is than the venal, corrupt wealthy noblemen who are usually his victims.
* Virgil's entire motivation in the ''Literature/LeagueOfMagi'' story "Dante Ascending." Of course, what he thinks are the Avalon Street Homeboys turn into something a lot stranger.
* In ''Literature/VoidMoon'', Cassie Black leaves the straight world behind to go back to her old life as a cat burglar. While the immediate motivation for returning to a life of a crime is the impending departure of her daughter, Cassie admits to herself that she really did enjoy being a criminal. She muses at length on the rush she always got while on a job.
--> "She remembered how after a while it hadnít even been about the money. It was about the charge it put in their blood. She remembered how they could stay up the rest of the night making love after a job was finished."

[[folder:Live-Action TV]]
* ''Series/BoardwalkEmpire'': Being set during Prohibition and TheRoaringTwenties, this show is full of this one. Half of the main cast are either really well-known gangsters (Arnold Rothstein, Johnny Torrio, Nucky Thompson, Jim Colosimo) or young gangsters just starting to make a name for themselves (the fictional Jimmy Darmody, and the very real Meyer Lansky, Charlie "Lucky" Luciano, and UsefulNotes/AlCapone). With very few exceptions most gangsters end up meeting the short end of a gun sooner or later, however.
* ''Series/{{Caprica}}'': Sam Adama, enforcer and hit man for the Tauron mob, caring uncle to [[TheCaptain William Adama]], and, well, possibly the ''coolest'' character in the show.
* ''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/GeneralHospital'': Weirdly seems to be the MO of the last decade of this show.
* ''Series/PeakyBlinders'': There are lots of montages and slow-motion sequences of the Shelbys partying or [[PowerWalk Power Walking]] down the street while badass blues-rock blares on the soundtrack.
* ''Series/{{Revolution}}'': Drexel in "[[Recap/RevolutionS1E6SexAndDrugs Sex and Drugs]]" believes in this trope. He's rich, powerful, fashionable, badass, has a lot of women surrounding him, and is certainly not bound by conventional morality. However, it is a SubvertedTrope, because he is a violent, AxCrazy thug who will get people killed because he thinks it's fun and games, and is politically incorrect towards a family of Irish cops who burned the poppy fields he uses for heroin. In fact, Drexel proves to be the opposite to such a degree that his surprising death at Aaron Pittman's hands is quite satisfying.
* ''Series/TheSopranos'' can make gangsters look so cool at times and so pathetically uncool at others. Working in the Mafia is shown to come with its perks, but we're also shown how much of the lifestyle is not so glamorous, and sometimes even outright scary. Sure, Tony has a nice house and makes a lot of money, but he has to face his boorish family all the time (and vice versa), suffers from depression and anxiety attacks, and he always has to worry about his "friends" turning on him, maybe leading to his arrest or assassination. As Christopher finds out when he finally gets made, the promotion means that he's under even more pressure to earn and is given more responsibilities, when he was expecting it to make his life a lot easier.
* ''Series/StarTrekTheOriginalSeries'': The gangster lifestyle in 1920's Chicago was so appealing to the inhabitants of Sigma Iotia II that the inhabitants of that world decided to [[PlanetOfHats build their entire society around it]].
* ''Series/{{Underbelly}}'': Attempts to dispel the myth that gangsters are cool, the bad guys are the JerkAss types who are put away by the few honest cops, or killed by the corrupt cops or each other. [[MisaimedFandom Don't stop idolization of Carl Williams and John Ibraham though]].
* ''Series/TheUntouchables'': InvertedTrope in the 1990s version: A boy gets some odd jobs from Al Capone's gang and finds he likes the bling involved. When Eliot Ness finds out, he drags the boy to a morgue to show what will likely happen to him if he wants to be a gangster. When the kid retches at the sight of a dead gangster with his throat bloodily slashed, he gets the point.
* ''Series/TheWire'': Omar. [[{{Gayngster}} Except the irresistible to women part.]]
* The {{Series/Yeralash}} short "[[https://www.youtube.com/watch?v=ijBoRu3ifwk Whom to be]]?" is about a boy's family telling him what they wanted to be in his age, only to hear that he wants to be a gangster (UsefulNotes/TheNewRussia in TheNineties was that kind of time). Suddenly, the chief gangster of the neighborhood flies through their window, alight after another bomb in his car, and tells the boy "You better dream about being an astronaut".

* A ''huge'' part of Hip-Hop and Gangsta Rap culture.
* The TropeNamer comes from Geto Boys' song "Damn It Feels Good To Be A Gangsta", probably one of the three songs the group is known for.
* Rap music is just as likely to deconstruct this trope as well, showing the downsides of being Gangsta: Sure you're badass, if you don't mind dealing with prison, drug addiction, friends dying young, your own life being in jeopardy, siring children out of wedlock, etc.
** [[Music/WuTangClan Raekwon]]'s debut album ''Only Built 4 Cuban Linx...'' is probably the TropeCodifier for gangsta rap deconstructing this trope.
** Music/TheNotoriousBIG's ''Ready to Die'' both plays it straight and deconstructs it, in that the first part of the album is comprised of the protagonist rapping about the issues he faces getting to the top, including his [[CrapsackWorld bleak surroundings]] ("Things Done Changed"), criminality ("Gimme the Loot"), people out to get him ("Warning") and the fact that he can die at any moment ("Ready to Die"). Only after he has made it do we get songs like "Juicy", "Big Poppa" and "One More Chance", which play it straight. Even then however, the album talks about how being a gangster (and a [[CelebrityIsOverrated celebrity]]) means he can't trust anybody ("Me and My Bitch") and how everything now is a struggle ("Everyday Struggle"). Eventually, on the album's last track ("Suicidal Thoughts"), he contemplates whether it's worth living at all.
** The Geto Boys deconstruct it themselves in "Mind Playing Tricks On Me", a harrowing depiction of what it's like to be a paranoid, guilt-ridden drug dealer, as does the song that named the trope, which stresses that if you are one, you'll know it and won't have to prove yourself; instead of talking, you act and let your actions speak for themselves.
* This is the whole point of the ''narcocorridos'' in Mexico. ''Narcocorridos'' are songs glorifying and glamorizing the culture of Mexico's [[TheCartel drug cartels]], many of them commissioned by the drug lords themselves to [[BoastfulRap boast about their exploits]].
* Music/Powerman5000's song ''Super Villain'' is this, just with {{supervillain}}y rather than regular gangbanging.
* Music/RabbitJunk's song ''Ghetto Blasphemer'' (itself part of a segment crossing black metal with hip-hop) features this phrase in its chorus ("Feels good to be a gangsta.")

* Creator/{{Capcom}}'s unreleased ''Pinball/{{Kingpin}}'' plays this trope as straight as a gunshot -- the player and the antagonists are all mobsters, and aside from death, any negative consequences of the lifestyle never arise.

[[folder:Tabletop Games]]
* In TabletopGame/{{Shadowrun}}, the player characters are specialized criminals for hire, living double lives on the wrong side of the law. The mega-corporations often use them as deniable/disposable assets for espionage and sabotage against each other, as well as "extraction" (kidnapping) and "wetwork" (assassination). Played especially straight with the 4th Edition supplement book Vice, which is unsurprisingly all about all the various forms of crime a runner can commit and the various criminal elements in the world that runners can work with, including rules for how to play a high-rolling Made Man.
** However, many professional Shadowrunners looks down on any Runner who tries to make an entertainment career out of it.
* One of the two major campaign options in ''TabletopGame/{{Spycraft}}'' is "freelance", where the players essentially operate their own small criminal organization, and it is invariably awesome.
* One of the many period-appropriate career choices for an Investigator or NPC in ''TabletopGame/CallOfCthulhu'', naturally. Depending on how high you roll for your spending level during character creation, being a gangster or criminal in general can be very, ''very'' lucrative indeed. That's not even counting how badass your character will look trying to gun down a shoggoth with a tommy gun.

* In ''Theatre/AnythingGoes'', Moonface Martin (posing as the Rev. Dr. Moon) is Public Enemy No. 13 and wants to be higher on the list (Mostly because ThirteenIsUnlucky). He helps a stowaway, Billy Crocker, pose as Public Enemy No. 1. At first the two of them are treated as celebrities, but when Billy's true identity is learned, they're both thrown into the brig. The greatest disappointment of his career is finding out that he's no longer a wanted man.
* In ''Theatre/ThePiratesOfPenzance'', the Pirate King's IAmSong--"It is, it is a glorious thing to be a Pirate King!"--makes an OlderThanRadio example. (On the other hand, these are mostly ThePiratesWhoDontDoAnything.)

[[folder:Video Games]]
* The ''VideoGame/GrandTheftAuto'' series.
** Subverted/averted in ''[[VideoGame/GrandTheftAutoIV GTA IV]]'', the main character, Niko, comes to America so that things can be different, after his life as a soldier, sailor and people-smuggler. His cousin's debts, bad blood with the Russian Mob, and his illegal immigrant status pulls him back to doing crime for money, but he in no way feels good about it. [[spoiler:And depending on the players actions, it ends up costing the life of his girlfriend or his cousin]]. [[DoNotDoThisCoolThing The player still might enjoy it though...]]
*** Subverted some more in ''VideoGame/GrandTheftAutoChinatownWars'' and ''The Lost And The Damned'' so far.
*** Ditto in ''The Ballad of Gay Tony'', since your main reason for breaking the law is to pay back debts to various criminals.
*** Super-duper subverted in ''Vice City Stories'', where the main character isn't even a criminal (and is probably the closest thing the game has to a good character) and is forced to engage in deviant acts by his drug-running commanding officer in the Army.
** Franklin Clinton of ''[[VideoGame/GrandTheftAutoV GTA5]]'' is an attempt at {{Reconstruction}}. He's sick of his gangbanging friends because they can't see how stuck-in-a-rut their lifestyle is while he dreams of taking his life to the next level...which means committing more ''sophisticated'' crimes. However his work for other people ends with him repeatedly being shafted in payment.
*** [[IndecisiveDeconstruction Other aspects of 5 subvert the trope,]] including [[spoiler:the brutal murder of fan favorite Johnny at the hands of Trevor,]] and Michael striking a deal with a government agent to escape his life of crime, with Michael and his partners later being forced to [[spoiler:torture and kill]] on the government's behalf in order to return the favor. Not to mention that two of the game's three endings require Franklin to [[spoiler:murder one of his closest partners.]]
** The online component of ''Grand Theft Auto V'' attempts to put the power into the ''player's'' hands. Start your criminal empire, build out your crib, and enjoy the high-octane lifestyle with your fellow online buddies at your wing.
* This sentiment is commonplace in ''VideoGame/MafiaTheCityOfLostHeaven''. While discussing the upcoming sequel, one of the developers called the game "a tribute to gangster movies" and claims this aspect will be [[DarkerAndEdgier toned down in the sequel]].
** 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.
** Averted with Vito Scaletta, the PlayerCharacter of the game. Even before things start going down in the last act, Vito had spent years in prison for stealing gas stamps so he could pay back a loan his mother inherited from her husband, she dies of sickness while he is in jail, his welcome back party ends up with him having to bury a corpse and it turns out everyone save for Joe tried to abuse his trust. By ''VideoGame/MafiaIII'', he is pretty jaded.
*** However he has a chance to see it either improve or get even worse after working with Lincoln Clay. On one end he would end up ruling together with him and re-establish a criminal empire even more powerful than ever or takes over Marcano's old businesses and legitimizes them in his stead and finally get what he wanted. Subverted with Cassandra and Burke if they rule alone as they drive the city to complete ruin and disappears/dies.
* Also [[SubvertedTrope subverted]] in the [[VideoGame/SaintsRow2 second game]] of ''VideoGame/SaintsRow''. The missions against the Brotherhood quickly become [[MoralEventHorizon mean-spirited]] enough to make some players uncomfortable.
** Not just the Brotherhood. What Gat and the Boss do to [[spoiler: Shogo Akuji--i.e. bury him alive while he begs, ''screaming'', for a MercyKill instead--]] also hit some players pretty hard. When it's not being balls out cool or fun, Saints Row 2 delves into some truly horrifying areas.
** Played straight in the rest of the game. Pimping out your hideouts, customizing your rides, building your gang, it's all really cool.
*** And in [[VideoGame/SaintsRowTheThird the third game]], the Saints have become a successful brand name. Crime is now so cool there is an energy drink named after your gang among other things, while you are still going on murderous rampages. Not only that, but there seems to be one "Professor Genki" who hosts [[DeadlyGame a game show involving death-traps and live firearms]]. In short, gansta cool seems to have left the building in favor of [[CrossesTheLineTwice comically over-the-top psychosis]] ''a la'' ''Film/DeathRace2000'' or ''VideoGame/TwistedMetal''.
*** It's implied the Saints "rob" banks as a publicity stunt, which they do by walking in, shooting the roof twice, and handing out autographs and photos while in Gat masks.
*** Subverted in the kill Killbane ending. The Boss choosing being a real gangster instead of a public icon it ends up with lieutnants dead and the Boss wondering if it was all worth it.
** By the fourth installment, the Boss is so cool, he's been elected ''President of the United States''. Saving the country from a nuclear missile helped a lot for P.R (even then he couldn't poll for shit according to his campaign leader before he was hired)
* Chains "Damn It Feels Good to Be a Robber" from ''VideoGame/PAYDAYTheHeist'' and ''VideoGame/PAYDAY2''. It helps that almost all robberies will result in at least one hundred grand in cash (most of which is sent to the swiss banks), and the blood of ''at least'' fifty courageous coppers on a non-stealth run.
* 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 cause the once childhoods 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 leads 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]].

[[folder:Visual Novels]]
* Wocky Kitaki is this in ''VisualNovel/ApolloJusticeAceAttorney''. He family are the biggest organized crime syndicate in the city, however despite them being a traditional and rather [[NeighborhoodFriendlyGangsters neighborhood friendly criminal organization]] Wocky himself is completely different, instead believing that being an "O.G" is all about living rough, not being scared of cops, killing people, and dying young. He even goes so far as to not care that he [[spoiler: has a bullet pressed up against his heart that could kill him at any moment (although it's implied that is slightly afraid of dying, he never lets these emotions known)]].
** This goes further. Wocky's father, the current head of the "Kitaki clan", wants to get out of the gangster life style and become a legitimate businessman, however Wocky doesn't want any of it believing that "a "G" can't be a "G" unless they are living the "G" life". Wocky eventually agrees to quite being a gangster however after [[spoiler: it's revealed that his father is trying to earn clean money in order to pay for a extremely expensive surgery that will save his live. His father doesn't want to use the money they have now because "it was the gangster life that nearly killed him", and he doesn't want to use the "money that nearly killed him" for the operation to save his life.]]
* ''VisualNovel/LuckyDog1'' shows the American Mafia in a pretty positive light despite the obvious dangers of associating with organized crime. This doesn't it mean it completely glosses over details like the gruesome punishment given to traitors of the organization or even the number of fatalities that can occur during mob wars, but for the most part it plays this straight.

[[folder:Web Comics]]
* ''Webcomic/{{Lackadaisy}}'': The CrazyAwesome [[strike:VillainProtagonist]] AntiHero is a whiskey and gin runner. Most of the other cast members are gangsters as well.
** Even if they're not specifically gangsters, many of them are either employees or patrons of the title speakeasy, and it takes place during the Prohibition. In other words: still criminals. The author even jokingly suggests that the little old lady who innocently tried to dispose of some bad sardines down her sink drain is a criminal based on sanitary disposal laws at the time.
* In ''Webcomic/{{Sinfest}}'', used in [[http://www.sinfest.net/archive_page.php?comicID=2952 this strip]]

[[folder:Western Animation]]
%%* ''WesternAnimationTheSimpsons'' did it at the end of [[http://en.wikipedia.org/wiki/Bart_the_Murderer this episode]].
* This example from ''WesternAnimation/FreaknikTheMusical'' when the Sweet Tea Mob meet Trap Jesus.
-->'''Trap Jesus:''' You think when I was nine, I wanted to trap?\\
'''Virgil:''' Uh, nope, no...\\
'''Trap Jesus:''' ''Hell yeah'' I did! I look around this city, see nothing but a gang of fiends on every corner of every block, and all I could think is, what a lucrative business opportunity. And ''now'' look at my swag. I'm the most ''biggest, notorious,'' dope man in the South. I'm a '''''BOSS.'''''
* Spoofed in several episodes of ''WesternAnimation/TheBoondocks''. It doesn't depict very many actual gangsters, but it devotes a fair bit of screen time to gangster-wannabes Ed Wuncler and Gin Rummy and gangster-themed GlamRap stars Gangstalicious and Thugnificent, portraying them as fools at best and dangerous criminals who set a poor example for black youth at worst.
--> '''Gangstalicious:''' That's why I'm always telling you kids, the drug game's cool, but in some ways... it's not so cool. But mostly it's cool.