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 Gun Grave 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.
Black Joke: All central characters are gangsters, and the crime world is depicted as very exciting and luxurious.
Films — Live-Action
The pirate equivalent in Pirates of the Caribbean. The pirate lifestyle in general is depicted to be a romanticized Bad Ass 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 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.
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....But the main character, in-universe and in Real Life, still wanted to be a gangster even after all that.
Public Enemies — 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 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.
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 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 Layer Cake 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 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!"
Completely averted in Killing Them Softly. Imagine The Sopranos cranked Up To Eleven. Set in 2008, it shows in detail exactly how much of an artifact the mafia has become. None of the gangsters drive flashy cars or live in nice homes. The hits are quick, brutal, bloody and done not out of a sense of honor but pragmatism (They murder a man They know to be innocent because people think he's guilty). The gangsters themselves are not mythic badasses but old, overweight, desperately trying to find some happiness and painfully aware of what pathetic symbols of the past They have become while the younger guys are stupid, desperate and violent. Perhaps best symbolised by the fact that a mob poker game, often seen taking place in a flashy nightclub, casino or hotel, is now held in a grey cheap motel room.
Vlad Taltos. Bit of a deconstruction in the later books of the time line, 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.
Boardwalk Empire: Being set during Prohibition and The Roaring Twenties, 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).
Caprica: Sam Adama, enforcer and hit man 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, he always wanted to be in a Mafia movie.
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.
The Sopranos: Can make gangsters look so cool at some times and so pathetically uncool at others. The show makes working in the Mafia look alternately paranoia-inducingly scary and mind-numbingly dull. 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), and he always has to worry about his "friends" turning on him, maybe leading to his arrest or assassination. When Christopher gets made, the promotion means that he's under even more pressure to earn.
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.
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.
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.
This is the whole point of the narcocorridos in Mexico. Narcocorridos are 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.
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 this phrase in its chorus ("Feels good to be a gangsta.")
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).
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 Spycraft is "freelance", where the players essentially operate their own small criminal organization, and it is invariably awesome.
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 Thirteen 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.
Subverted/averted in GTA IV, the main character, Nico, 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. 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...
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.
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.
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.
While the game certainly glamorizes the life of a modern gangster - and the characters themselves definitely enjoy this lifestyle - it does have one notable subversion: as cool as the protagonists are, it still isn't enough to make up for the horrific acts they commit and their general sociopathy. Moreover, although this is subject to interpretation, it can be seen that this is supposed to be how the audience reacts.
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" in a nyancat suit driving a clown car with a cannon that ejects pedestrians. In short, gansta cool seems to have left the building in favour of Death Race 2000 or Twisted Metal style mass psychosis.
Wocky Kitaki is this in Apollo Justice: Ace Attorney. He family are the biggest organized crime syndicate in the city, however despite them being a traditional and rather neighnorhood 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 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 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 us the "money that nearly killed him" for the operation to save his life
Lucky Dog 1 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.
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.
Trap Jesus: You think when I was nine, I wanted to trap? Sweet Tea Mob: 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.
/b/ sure tries to present itself this way. The rest of the site, not at all.
Hill: This animal thing here, this is the longest I've ever been attached to a game. Julian (Hill's son), I could play this with your mother. Give us something in common. Besides sex. Julian:Oh, God. Can we go now?
While not presented as "cool" necessarily, there are a number of common laws that are widely regarded by the public as either bad laws in themselves, or laws so badly enforced that they might as well be. The people that break these laws are thus regarded in a relatively positive light or outright heroic:
Internet pirates sometimes get this treatment due to the RIAA/MPAA's tomfoolery.
One man's freedom fighter is another man's terrorist.
A more specific example might be Julian Assange, one of the founders of Wiki Leaks. Whereas many government officials and representatives see him as a criminal who discloses state secrets, many people in the public see him as someone who values the truth most and just wants to make sure governments don't abuse their power.
Same with Edward Snowden. Enough said.
Common in the 1990s with marijuana users and dealers due to backlash against recreational drug prohibition in the US. Less common recently as the major suppliers of marijuana to the US, the gangs of northern Mexico, sank into a bloody series of turf wars funded primarily by US drug money.