Cinema has a habit of making gangsters look cool. Yep, the big screens just can’t get enough of the bad guys. But it’s not just the romantic tough-talk, the bloody action and the glitzy allure of high-flying mobsters that gets us. The gangster genre shows us how criminal networks operate with their own fiercely moral codes; recognisable and even relatable for those of us who’ll never wield a sawn-off shotgun. Call it an offer you can’t refuse, gangster flicks are intoxicating. And here are the 20 best ones out there.
Infernal Affairs (2002) Wai-Keung Lau, Alan Mak
Mixing eye-popping action with existential steez, Infernal Affairs has something more mystifying than any gangster flick before it. What makes it special is the inner turmoil caused by living a lie. If everyone you know and everything you do indicates you are one kind of person and you’re not that person, how d’you live with that? The simple concept of a police mole among the Triads and a Triad mole among the cops – each racing to uncover one another – is the hook for a complex network of suitably tense crosses that have us hugging ourselves with excitement each time we sit down to revisit Chan Wing-Yan and Lau Kin Ming.
The Godfather I-III (1972-1990) Francis Ford Coppola
Coppola’s trilogy constitutes one of the greatest in cinematic history and – through an ingenious fusion of European cinema and American exploitation movies – an outstanding study of family life and organised crime falls into place. The films don’t spoon-feed answers and motivations. In fact, Coppola took a pulpy, salacious novel and pretty much turned it into a bunch of guys sitting around in dark rooms, murmuring. But, every review praises the living hell out of The Godfather trilogy. You know why? Because it’s the perfect character-drama. Few films ever made have been able to get the audience up to speed on so many members in such a short period of time. Brando created one of the most iconic characters in the history of movies with a couple of cottonballs in his mouth and you can virtually see Al Pacino’s inner struggle and decision to finally and irrevocably cross the line.
Pulp Fiction (1994) Quentin Tarantino
“I – say – God – DAMN!” Still one of the most quotable films today, Pulp Fiction managed to synthesize the serious brutality of gangster movies before it with the wacky violence of cartoons and the kind of directionless excitement that only Tarantino can conquer; all to the story of a burger-loving hit-man, his philosophical partner, a drug-addled gangster’s moll and a washed-up boxer. A huge part of what makes this movie so massively memorable is the riffing dialogue that seamlessly combines humor and terror in intelligent conversations. From the very first words uttered, you know you’re watching something special.
Goodfellas (1990) Martin Scorsese
The allure of the mafia is what this visceral view of New York’s gangster scene is really all about. To Henry Hill – who’s based on the real-life crook of the same name – joining the mob is a valid career choice. We’re taken on a seductive tour of a restaurant meeting between “good fellas” and “wise guys” (yep, the screenplay is based on true-crime author Nicholas Pileggi’s bookWiseguy) and made to covet the bling of gangsterdom; cars, watches, women. But later, we share the hero’s tragic-but-not-undeserved downfall. He’s no anti-hero. He’s no victim. He’s a dirty criminal who descends into a fidgety, paranoid mess. Somewhere, though, the real Henry Hill is still laughing; he got the fame he always craved!
Bonnie and Clyde (1967) Arthur Penn
Although the real Bonnie and Clyde lived during the ’30s, the 1960s flick just reinforces the fact that it’ll never be hard to relate to their story, because it builds upon the human desire to escape the tedium of life and enjoy being free. Everyone back in ‘67 was sticking it to authority and these two were certainly no different. As the criminal couple fall steadily in love with each other, they revolutionise the way sex, terror, and ferocious violence played out in world cinema. The movie depicts a kind of a glamourous vivacity that is still present in the gun battles of today’s gangster flicks. And, for better or for worse, going out struck down by a mighty hail of bullets never looked so goddamn cool.
Lock, Stock and Two Smoking Barrels (1998) Guy Ritchie
Ritchie took the cheeky, cockney charm of Alfie and propelled it into the ’90s with some distinct nods to Tarantino, some flashy camera effects, and a contrived plot in which a group of East End Londoners spend a frantic couple of days trying to raise half a million to pay a gambling debt (it doesn’t make for an easy heist). Whatever else, Lock, Stock is full of swag and helluva fun; the movie comes alive every time the rock-heavy soundtrack rears its head; the narration peppers its audience with sarcastic shotgun pellets; the guys sip drinks with umbrellas in them. Things turn to absolute chaos by the movie’s final hour and – thanks to the sadistic drug barons, pot-growers and porn kings – it never runs out of steam.
The Departed (2006) Martin Scorsese
Scorsese’s Boston-based undercover crime thriller is actually a remake ofInfernal Affairs and, as such, the premise should sound pretty familiar: A police officer is actually a mole sent in by a gang to find out what the cops have on them while a police office is infiltrating the same gang; a mental chess match occurs. The Departed wins its own place on this list though – not least because it marks Matt Damon and Leonardo DiCaprio’s best performances to date. Whichever way you look at it, the movie is an absolutely brilliant Americanization of a great Chinese film. While Infernal Affairs does cool, elegant symmetry between the two protagonists flawlessly, Scorsese’s version (feeling a lot like the stuff of his golden years) dots the i’s, crosses the t’s, and puts Dropkick Murphys on the soundtrack.
Reservoir Dogs (1992) Quentin Tarantino
Tarantino has long wanted us to know about his capacity for dreaming up controversial dialogue and savage violence. He’s an auteur known for kitsch and gore; Reservoir Dogs is no different in that respect. In fact, the film’s unsettlingly tragic ending gives us a sense of Tarantino as a master of excess. Yet, with the portrait he paints of the ill-fated friendship between Mr. White and Mr. Orange and how he shows the bad guys wiling away the boring hours between jobs, the movie is also a window into the everyday (and sometimes quite mundane) life of individuals. It’s unexpectedly moving.
Scarface (1983) Brian De Palma
When the ‘83 remake movie arrived in theatres, it was seen by many as shallow – at least in comparison to Howard Hawks’ original Scarface of 1932. Apart from the new Scarface being endlessly quotable, however, it also documented the vicious side of the American underworld in a way never done quite so tastelessly. There’s nothing understated about the Al Pacino-starring flick following the rise and fall of Tony Montana and telling a satirical tale of greed. Set to the backdrop of drugs and chainsaws, the celebration of materialism is garish and glaring, with the final scene descending into a huge orgy of violence. Whatever people thought of the movie back then, it became a phenomenon. It’s 100% over-the-top and that’s exactly what makes it awesome.
The Usual Suspects (1995) Bryan Singer
Who IS Keyser Söze? One of the most inventive gangster flicks of all time,The Usual Suspects absolutely nailed it with its macabre, serpentine journey into the dark corners of the criminal mind. A bent cop, a comic burglary double act, and a “cripple” are among the not-very-usual suspects being blamed for a massacre on the shipping docks of LA. It’s funny, it’s scary, and it’s got a whopper of a surprise ending. One so good, in fact, that it makes you want to rewatch the movie almost immediately and catch Singer out on parts of the story that don’t fit. Unfortunately, as far as twists go, this one is seamless.
Donnie Brasco (1997) Mike Newell
Before Johnny Depp became the master of over-accessorizing and got somewhat lost among his own neckerchiefs, he was doing cool things like gangster movies. Enter: Donnie Brasco. Depp’s turn as Joseph Pistone is a clever move. As an FBI agent, he’s granted access into the mob family of Lefty (Al Pacino, nonetheless) and as the two get closer, their loyalties blur. As Donnie, Depp is so effortlessly convincing that when he amps up the “tough guy,” it’s easy to forget he was once the small-town, softly-spoken Gilbert Grape and is now draped heartily in silk.
Léon: The Professional (1994) Luc Besson
A character-driven gangster flick that delivers a disturbing coming-of-age story (that’s the uncut version, y’all) with the stylish action and thrills any cinephile has come to expect from a Luc Besson movie. Jean Reno plays a loner hitman whose only pleasure in life is the odd glass of milk and a trip to the pictures. When almost all of the family next door are gunned down by crooked cops, he takes Natalie Portman under his wing and sets about taking out Gary Oldman and co. Nobody – NOBODY! – can do evil like Gary Oldman and his mad contortions.
Ghost Dog: The Way of the Samurai (1999) Jim Jarmusch
The concept of Ghost Dog is wonderful: a hitman played by Forest Whitaker follows the code of the samurai. But the film is so much more than that. It’s a reflection on race, death, and the mythical… a “spiritual gangster movie,” if you will. Jarmusch manages to transform the samurai into some kind of phantom that only Wu-Tang’s RZA can see. It’s one weird, genre-bending flick that only gets away with its own far-out style because it doesn’t take itself too seriously. A massively seductive movie.
On the Waterfront (1954) Elia Kazan
Kazan’s gripping study of mob culture and corruption along the docks in New York is that rare cinematic jewel that is – in equal parts – romantic and climactic. The role of gutsy whistleblower Terry was first offered to Frank Sinatra, but it was Marlon Brando’s beefcake that won the role. Luckily, too, because On the Waterfront changed the face of gangster movies with its emphasis on naturalistic acting. Brando managed to convey a melancholy that few other actors have ever matched, in telling his audience that he “really coulda been somebody…” Arguably Brando’s best role.
True Romance (1993) Tony Scott
Given that the screenplay comes from Tarantino, it’s hardly surprising thatTrue Romance exudes the kind of casual concern we’re used to seeing in his other flicks. Christian Slater is somewhat of a genius for creating cooler-than-thou weirdos – especially ones who get the girl – and in True Romancehe manages to pick up the gorgeous Alabama (Patricia Arquette) just by being a comic-book nerd. Alabama’s pretty great, too. As things start to unravel in typical Tarantino style – loaded guns, stolen drugs, and lots of bloodshed – she’s the four-day hooker who’s sugary innocence keeps everything together right up until the end.
The Killing (1956) Stanley Kubrick
If you haven’t yet seen Kubrick’s The Killing, then you’ll want to remedy that as soon as possible. It’s a little noir film that Tarantino borrowed heavily from for Reservoir Dogs and probably the best “just one last job before we retire” gangster movie ever made. Kubrick’s third feature film (which he made at just 27-years-old) follows a career criminal who assembles a mob for a racetrack heist that’s going to get him enough cash to be able to marry his woman. Don’t these gangsters ever learn? As predicted, the plan is foiled and everything goes to sh*t. But – as one of Kubrick’s most perfect films – it’s sure as hell fun to watch.
Casino (1995) Martin Scorsese
Criminally good, Casino is nothing less than a Scorsese masterpiece, based on the true story of the violent life and death of Tony “The Ant” Spilotro, the mob’s chief enforcer during the early 1970s. For those interested in the development of the American mafia, Casino is a fantastic translation of the gaudy haven for high rollers of that time and brings the dusty pages of Las Vegas history to life. It’s glitzy, glam, and seedy, with the best psychotic sidekick in movie history; Joe Pesci’s Nicky Santoro.
City of God (2002) Fernando Meirelles
The exhilarating and insanely violent portrait of young lives gone wrong in the shanty towns of suburban Rio is an exciting insight into the resurgence of Latin American cinema. Director Meirelles does some pretty innovative things with the camera, despite guiding a cast of unknown actors who were chosen from the slums of the city and had never before acted. Selected for their charisma, the boys were trained in improvisation for six months – and it shows. The coming-of-age gang-warfare picture is as impressive as they come.
Jackie Brown (1997) Quentin Tarantino
We all wondered where Tarantino would dare to tread after Pulp Fiction; he chose a surprisingly safe option by telling the story of Jackie Brown, based on a book called “Rum Punch.” It’s a solid movie (although not in the same league as Tarantino’s preceding flicks), but what makes it special is the major league cast. Pam Grier reestablished her career with her amazing performance which echoes her previous blaxsploitation flicks like Foxy Brown. But, unsurprisingly, it’s Samuel L. Jackson as wild antagonist Robbie who really steals the show.
Get Carter (1971) Mike Hodges
Before Get Carter, movies always seemed to assume that gangsters were either stupid or funny. But, this bleak and violent portrayal of criminal life saw Michael Caine and director Hodges paint a grim, grey picture of Northern England that was far more brutal than anything British cinema had seen before. In fact, when the movie surfaced for the first time, the British reception to it was cold. Perhaps Caine’s turn as a remorseless killer in a bleak, twisted world of corruption was too much for audiences back then. And don’t be fooled by Caine’s totally un-badass haircut, either. It was 1971 and that was kind of an “anything goes” time…