Criminals are cool. It might be a terrible thing to say, but it's true (at least, in fiction). One of the most enduring images in modern fiction is that of the glamorous gangster — a streetwise, Self-Made Man who's rich, powerful, badass, irresistible to women, fashionable, and unfettered by conventional morality. In short, a perfect Escapist Character for times when being a good guy is just too dull.
Violence might be abhorrent in Real Life, but on the big screen it can be just another way to get the audience's adrenaline flowing, and there's nothing wrong with that. Besides, in fiction, it doesn't matter how many dogs you kick as long as you look really cool when you do it.
The critic Robert Warshow wrote a famous essay called The Gangster as Tragic Hero, in which he posited that gangsters like those in Scarface are Americanized versions of Greek or Shakespearian tragic heroes, dark mirrors of The American Dream, or the "great no" to the American promise of success. He argued that they were a counter to the films made in The Golden Age of Hollywood, and were a form of Wish-Fulfillment for working-class audiences with their Rags to Riches stories and charismatic, tragic characters. Even when Executive Meddling had the bad guys getting punished, the filmmakers and actors conspired to give the villain protagonists a memorable death scene that made audiences Cry for the Devil, similar to classic tragic heroes and villains. This essay made a big impact on the likes of Francis Ford Coppola and Martin Scorsese and informed their Genre Deconstruction in The Godfather and Goodfellas; in the case of The Godfather it was essentially an Unbuilt Trope.
This trope was widely popularized in the US during The Roaring '20s when Prohibition made organized crime big business and the gangster became one of the iconic figures of the era; and The Great Depression, where bank robbers were seen as striking at the greedy and foolish banks that got the country into this mess. Of course, it has 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 than play it straight. Indeed, the "rise and fall" narrative has become such an integral part of the gangster genre that it now makes straight examples of this trope nigh impossible.
This trope is also a huge part of Hip-Hop culture, as shown by the name of the Gangsta Rap genre. Many rappers play this trope straight, writing Boastful Raps about all the money they make from pimping, drug dealing, and robbery, while music videos show them driving luxury cars and wearing loads of jewelry while surrounded by strippers in their mansion (all implied to have been purchased with money earned through the aforementioned illicit means). However, other rappers are just as likely to deconstruct this by showing the downsides of being a 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...
In Mexico, there's also the narcocorridos (drug ballads), songs glorifying and glamorizing the culture of Mexico's drug cartels, many of them commissioned by the drug lords themselves to boast about their exploits.
When the cool criminal is the lead character, they're probably a Villain Protagonist or Anti-Hero. Their PR may be helped by only doing crimes against a Asshole Victims, as in a Karmic Thief or Sympathetic Murderer.
Sub-Trope of Evil Is Cool and closely related to Do Not Do This Cool Thing. A direct opposite of Being Evil Sucks. See also Neighbourhood-Friendly Gangsters and Draco in Leather Pants. If the criminals aren't ever shown actually doing anything, well, criminal, they're The Pirates Who Don't Do Anything. Criminals who believe in this point of view may opt to be Just a Gangster and turn down chances to leave their criminal life behind.
- Mello from Death Note. He took over the mafia, and spent most of his time in it wearing leather, eating chocolate, lounging on a garish zebra-print sofa (or sometimes a decadent leather chair), and making Manipulative Bastard Light and Teen Genius Near look like idiots.
- 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 Light Novels, 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 Abominations want in on it. Just ask Ronnie.
- Mostly avoided in the 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 Black Lagoon. Although The Lagoon Company and Balalaika's 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.
- JoJo's Bizarre Adventure: Golden Wind is a Reconstruction of the trope. one of the central themes is that a moral code is just as important to the idea of a gangster as the style and luxury shown off. The Arc Words from the villain are "Only the Results," and the story goes out of its way to show how wrong they are.
- Gangsta.. is all about this. The coolest and most sympathetic characters are either mafioso, prostitutes, crooked cops, or Ax-Crazy Differently Powered Individuals.
- Black Joke: All central characters are gangsters, and the crime world is depicted as very exciting and luxurious.
- Reborn! (2004) and its mafioso families who are very badass. There are ten of 'em and It Runs in the Family.
- Bungou Stray Dogs: The Guild are a bunch of international people 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 (which also counts for this trope) and at present still lives in fear of them despite her Heel–Face Turn.
- Shouwa Genroku Rakugo Shinjuu 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.
- In the Power Man and Iron Fist (2015) series, Alex Wilder says this word for word after viciously taking over one of the gangs in Harlem.
- In the 1989 film All Dogs Go to Heaven, 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.
- The pirate equivalent in Pirates of the Caribbean. 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.
- The Godfather 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.
- Scarface (1932) deconstructs this. Also applies to the Scarface (1983) remake with Al Pacino, which remains hugely popular to this day with the Misaimed Fandom.
- Arthur Penn's heavily fictionalized portrayal of the title bank robbers in Bonnie and Clyde, one of the original "New Hollywood" films, is a very influential example.
- Goodfellas is arguably the purest and most famous example of all time, despite also being known for its more "gritty" take on The Mafia. 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 Real Life, still wanted to be a gangster even after all that.
- Casino, with Robert De Niro, Joe Pesci and Sharon Stone. Even though it might show the illicit and brutal elements of the Mafia, the fact that it's set in the very glamourous city of Las Vegas offsets those aspects of the film's story.
- Another Scorsese film The Irishman 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.
- Reservoir Dogs and Pulp Fiction are often considered deconstructions of this trope, but they're still ridiculously cool.
- Guy Ritchie movies in general, i.e. Lock, Stock & Two Smoking Barrels, Snatch., Rock N Rolla.
- Fight Club made it look so cool to be in such a club that it was pretty much inevitable that some people started their own.
- Public Enemies
- 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 Truth in Television 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.
- Eastern Promises, 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 turns out to be The Mole.
- Angels with Dirty Faces: 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 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.
- Daniel Day-Lewis' show-stealing performance as Bill the Butcher in Gangs of New York is made of this trope.
- American Gangster 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.
- The film version of Layer Cake subverted this trope while deconstructing it. At first, the protagonist makes dealing cocaine look like easy, stylish money with an 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 Black Comedy just how lame the criminal underworld can be.
- In Bugsy Malone, the song "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.
- Sin City 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. And in some cases, they outlive the heroes but usually at great cost.
- Averted in Alpha Dog. 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 King of New York. 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 Johnny Dangerously, 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 "Weird Al" Yankovic: "If money can't buy happiness, I guess I'll have to rent it!"
- In Atlantic City, 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 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 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 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 Psychopathic Manchild 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.
- The Act of Killing 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 The Limey. "I embrace this lifestyle," insists Stacy the Hitman, only to be knocked off well before the credits roll.
- A Bronx Tale: 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 he just did what he had to do and C would be better off going to college.
- American Animals: 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."
- Lord of War has Yuri Orlov, a small-time gunrunner turned giant. It's true that in building a successful arms empire, he inevitably loses his literal brother in crime and his family, on top of becoming nothing more than a pawn of powerful governments (and an enabler for genocide-mongers). But it remains that Yuri will always be wealthy, he loves what he does, and he is enough of a "necessary evil" to have a more or less permanent Get Out Of Jail Free card.
- In Broken Arrow (1996), 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?"
- Zett Nilric in Star Trek: Vanguard, who is elegant, mannered, and sharply dressed to a fault, an expert swordsman, and definitely has a certain flair. Another example from the Star Trek Novel Verse is Ihasz, who shows up in ''A Time To Heal'' and ''Articles of the Federation''.
- Dragaera series protagonist Vlad Taltos. Bit of a deconstruction in the later books of the timeline, but Taltos in particular is made of this.
- 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 League of Magi story "Dante Ascending." Of course, what he thinks are the Avalon Street Homeboys turn into something a lot stranger.
- In Void Moon, 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 crime is the impending departure of her daughter, Cassie admits to herself that she really did enjoy being a criminal. She muses at length about the rush she always got while on a job.
"She remembered how after a while it hadn’t 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."
- The Shivers novella, Babyface & the Killer Mob, revolves around a 12-year-old kid who frequently daydreams of joining the local Miami mob, even pestering gangsters from the titular mob to take him in - and threatening to rat them out if they rejected him. He gets his wish alright when he unexpectedly wakes up in an adult's body, working as the Killer Mob's getaway driver. until the story's ending where it turns out his misadventures are All Just a Dream after getting hit on the head.
- A comic book version of it is the basis for The Supervillainy Saga. Protagonist Gary Karkofsky is a wannabe supervillain for virtually his entire life and finally becomes one after getting a magic cloak. He proceeds to become involved in all sorts of criminal activity and fighting fellow supervillains. By later books, he's immensely rich but also has suffered numerous personal tragedies.
- In 365 Days (and the film adaptations), aside from being occasionally kidnapped or otherwise placed in mortal danger, Laura's life as a Sicilian Mafia boss' lover is portrayed glamorously; she lives in a lap of luxury with expensive material goods galore and access to anything she desires, and there seems to be few limits to Massimo's wealth and influence. Massimo and his criminal/romantic rival Nacho are both portrayed as extremely attractive, and Laura being desired by these men is presented as sexy and exciting.
- Boardwalk Empire: Being set during Prohibition and The Roaring '20s, 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 Al Capone). With very few exceptions most gangsters end up meeting the short end of a gun sooner or later, however.
- Caprica: Sam Adama, enforcer and hitman for the Tauron mob, caring uncle to William Adama, and, well, possibly the coolest character in the show.
- Community: As far back as Abed can remember in "Contemporary American Poultry" (a Whole-Plot Reference to Goodfellas), he always wanted to be in a Mafia movie.
- General Hospital: Weirdly seems to be the MO of the last decade of this show.
- Narcos devotes a huge portion of its running time to chronicling the extravagant lifestyles of the Colombian and Mexican drug traffickers while also showing how violent and deadly such a career choice is.
- Peaky Blinders: This series justifies, deconstructs and reconstructs it at the same time. This is justified by the fact that criminals were on the rise after the first world war, with the police being openly corrupt and many of them having formed an organization of their own. It also deconstructs by making it very clear that high-level professional criminals do indeed have vast wealth and resources, but they are unreliable, many are mentally unstable and are horrible people who have no moral principles who do what they do for pleasure, money and power, not out of necessity (What interests the Shelbys is how they can do whatever they want without consequences because they are influential violent criminals with many resources and explicitly state this several times throughout the series). And he rebuilds with Tommy and some of his allies and enemies who, in particular, are very aware of the misery they spread and really don't ignore it, but think it's worth it because of the professional success he's achieved, as long as it doesn't harm their loved ones and there are lots of montages and slow-motion sequences of the Shelbys partying or doing a Team Power Walk down the street while badass blues-rock blares on the soundtrack . Not to mention a very important detail that all viewers ignore: All the protagonists of this series are really horrible people and cruel criminals with almost no remorse for their actions .
- Revolution: Drexel in "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 Subverted Trope, because he is a violent, Ax-Crazy 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.
- Zig-zagged and deconstructed in The Sopranos. The show can make gangsters look cool at times and uncool at others. Working in The Mafia has its own 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 is relatively well-off, 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 Tony's nephew Christopher finds out the hard way when he finally gets made, the promotion means that he's under even more pressure to earn, when he was expecting it to make his life a lot easier.
- Star Trek: The Original Series: In "A Piece of the Action", 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 build their entire society around it.
- 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. Don't stop idolization of Carl Williams and John Ibraham though.
- The Untouchables: Inverted Trope 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.
- The Wire: Omar. Except the "irresistible to women" part.
- The Yeralash short "Whom to be?" is about a boy's family telling him what they wanted to be at his age, only to hear that he wants to be a gangster (The New Russia in The '90s 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".
- The Trope Namer comes from Geto Boys' song "Damn It Feels Good to Be a Gangsta" used in Office Space, probably one of the three songs the group is known for. The song is a reconstruction of the trope, describing how a "real" gangsta should be (cool, hard-working, not starting fights but able to win one if needed) while calling out "fake" ones who talk big but can't back up their words. In the end, the song also compares the President of the United States to a gangster. The Geto Boys also 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.
- Grandmaster Flash and the Furious Five deconstructed it before gangsta rap was even a thing with "The Message" by making it clear that while the thug life is definitely attractive when you're young, poor, and don't see the point of school and don't want to be a working stiff who can never make ends meet, it will have violent, humiliating, and life-ruining consequences.
- The Notorious B.I.G.'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 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 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.
- Powerman 5000's song Super Villain is this, just with supervillainy rather than regular gangbanging.
- Rabbit Junk's song "Ghetto Blasphemer" (itself part of a segment crossing black metal with hip-hop) features the phrase "feels good to be a gangsta" in its chorus.
- Subverted in Eminem's early Gangsta Rap material. In his serious songs, being a gangster is a horrible, degrading experience and something he only does due to humiliating poverty. In his silly songs, Slim Shady is a loser who spends way more time committing pointless antisocial acts than doing anything that will make him money, constantly talks about killing himself because he hates himself so much, and is only able to attract unappealing, diseased women.
- Our Miss Brooks: In "Sunnydale Finishing School", Miss Brooks receives a letter offering her a position at the eponymous school. Walter Denton, utilizing a Zany Scheme, pretends to fall victim to this trope and begins acting like a mobster while speaking in a blizzard of hard-boiled slang.
- In 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 look down on any Runner who tries to make an entertainment career out of it.
- One of the two major campaign options in 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 Call of Cthulhu, 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 Anything Goes, Moonface Martin (posing as the Rev. Dr. Moon) is Public Enemy No. 13 and wants to be higher on the list (mostly because 13 Is Unlucky). 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 The Pirates of Penzance, the Pirate King's "I Am" Song—"It is, it is a glorious thing to be a Pirate King!"—makes an Older Than Radio example. (On the other hand, these are mostly The Pirates Who Don't Do Anything.)
- In West Side Story, the Jets' Song talks about how great it is to be a Jet.
- The Grand Theft Auto series.
- Played completely straight in Grand Theft Auto: Vice City. While Tommy Vercetti starts the game in the dumps after a failed deal and has to work hard to earn back the fortune he lost, dealing with enemies both within and without... By the end of it, he owns the entire city's underbelly, all his rivals are dead and he's free to enjoy his fabulous life.
- Subverted/averted in 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 Mafia, and his status as an illegal immigrant from Serbia pulls him back to doing crime for money, but he in no way feels good about it. And depending on the players' actions, it ends up costing the life of his girlfriend or his cousin. The player still might enjoy it though...
- Subverted some more in Grand Theft Auto: Chinatown Wars 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 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.
- Other aspects of 5 subvert the trope, including 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 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 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 Mafia: The City of Lost Heaven. While discussing the upcoming sequel, one of the developers called the game "a tribute to gangster movies" and claims this aspect will be toned down in the sequel.
- Although Mafia II 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 Player Character 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 Mafia III, 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 subverted in the second game of Saints Row. The missions against the Brotherhood quickly become mean-spirited enough to make some players uncomfortable.
- Not just the Brotherhood. What Gat and the Boss do to Shogo Akuji—i.e. bury him alive while he begs, screaming, for a Mercy Kill 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. He also tells Julius this more or less before his death in the secret mission.
- And in 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 a game show involving death traps and live firearms. In short, gansta cool seems to have left the building in favor of comically over-the-top psychosis a la Death Race 2000 or Twisted Metal.
- 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 ends up with lieutenants 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 PAYDAY: The Heist and PAYDAY 2. 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 Sleeping Dogs, 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 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. 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 Trauma Conga Line and Wei barely survives.
- Deconstructed in the Yakuza series. When the first game begins, Kiryu is on his way to being a made man; but after Taking the Heat 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 Yakuza 0, 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.
- Wocky Kitaki is this in Apollo Justice: Ace Attorney. His family is the biggest organized crime syndicate in the city, however despite them being a traditional and rather 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 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 lifestyle 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 quit being a gangster however after it's revealed that his father is trying to earn clean money in order to pay for an extremely expensive surgery that will save his life. 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.
- Deconstructed with both Morgan and Lauren in Double Homework. The two used to be in a gang together, but their first real criminal act, an armed robbery, went horribly wrong. Morgan went to prison for a year, Lauren tried to act classier after her escape, and the rest of the gang went their separate ways. Notably, Lauren and Morgan would never get along after the robbery.
- Lucky Dog 1 shows the American Mafia in a pretty positive light despite the obvious dangers of associating with organized crime. This doesn't 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.
- The Villain Protagonist is a whiskey and gin runner.
- Even if most of the cast aren't specifically gangsters, many of them are either employees or patrons of the title speakeasy, and it takes place during 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 every mid-review overdubbing by CJ DaChamp, every character is presented like they're the lead in a Gangsta Rap song. As such, alcohol, guns, and getting laid are presented as universal goals for everyone.
- The Simpsons did it at the end of "Bart the Murderer". Bart has gotten declared innocent for the murder of Principal Skinner when a very alive Skinner storms into the courtroom and asserts his innocence. Bart then opines that crime doesn't pay, and Fat Tony sadly agrees ... before he and his men climb back into their huge expensive limousines to drive away.
- This example from Freaknik: The Musical when the Sweet Tea Mob meets 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 The Boondocks. 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 Glam Rap 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.
- Batman: The Animated Series, Arnold Wesker was a Ventriloquist who had Dissociative Identity Disorder. Unwittingly, Wesker developed a criminal mastermind personality which was vented through the dummy named Scarface, who is modeled after the Trope Maker and Trope Codifier of this very trope), but not the Ventriloquist: At "Read My Lips", we see Scarface sleeping in a huge bed located in a luxurious room with large windows, with cookies, water and a cigarette in his desk. Then we see that the Ventriloquist sleeps in a small dilapidated room with broken windows, wearing only a nightgown. The Ventriloquist lives in Scarface's closet. Scarface is Cigar Chomper, his clothes are elegant and he is a Bad Boss, while the Ventriloquist endures Scarface making fun of his only suit and is an Extreme Doormat.
- This is the basic idea behind The Goodfeathers. They're expies of various actors from gangster movies and are themselves wannabes constantly trying to make a good impression on the Godpigeon and become wise guys. While being a full-fledged gangster appears to be awesome, being a wannabe makes you a Chew Toy.