The 50 greatest gangster movies of all time

Hong Kong thriller Triad Election – a sequel to Election, though you needn’t be familiar – wallows in the filthy gutters of the underworld as crime bosses orchestrate a peaceful transfer of power. That clearly doesn’t happen. Director Johnnie To – in one of the grounded entries on his prolific CV – stages all manner of ugliness with gritty panache, from chaotic gunfights to a grisly sequence involving a lackey, a saw and a pack of starved dogs (grounded, in To’s case, involves a meat grinder). The auteur might have directed a better crime thriller in Drug War, but the gritty gangland audacity of Triad Election stands apart in its singular brutality. 

‘Afghanistan banana stand.’

You've seen plenty of gangster and crime movies that build to a heist, but The Hot Rock is a string of heists that take place as a result of unforseen circumstances. Robert Redford and George Segal play against type, presenting themselves as hardened crooks, but ultimately revealing that they're extremely fallible. And just wait until you hear the funky soundtrack that Quincy Jones cooked up for this crime comedy of errors.

‘All men are guilty. They're born innocent, but it doesn't last.’

Calm, cool and quiet, the films of French New Wave progenitor Jean-Pierre Melville don’t rush to action, or anything else. But his penultimate film, involving three crooks who meet by chance and band together to pull off a big job, has a cracking centrepiece: a near-silent, 30-minute jewel heist, à la Rififi, that’s so hypnotic it’s like the crime version of transcendental meditation.  

‘I've been kicked around all my life, and from now on, I'm gonna start kicking back.’

He’s a gangly reform-school graduate with a morbid fascination for firearms. She’s a rodeo sharpshooter with the best eye (and legs) in the business. This lovers-on-the-run classic is tougher and sexier than Bonnie and Clyde (if not as iconic), and the single-shot getaway sequence is breathtaking.

‘Listen to me very carefully. There are three ways of doing things around here: the right way, the wrong way and the way that I do it.’

Scorsese laid on the style for this Goodfellas-like rise and fall centered on the gambling scene in Las Vegas in the 1970s and ’80s. Robert De Niro plays a mob-appointed casino boss whose troubled trajectory symbolizes the sunset years of the Mafia’s grip on the city.

‘An old lady on Main Street last night picked up a shoe. The shoe had a foot in it. We're gonna make you pay for that mess.’

The greatest testament to Orson Welles’s seedy border noir is that it isn’t defined by its legendary opening shot, the long take to beat all long takes. Charlton Heston plays a Mexican newlywed investigating an explosion on the U.S. side of the fence, but his inquiries hit a wall when he collides with an American police captain (Welles at his largest, in more ways than one), who may be the meanest gangster in town.

‘You guys got fat while everybody starved on the street. Now it's my turn.’

The wild and wonderful Christopher Walken never had a better showcase for his inimitable charms than the role of Frank White, a ferocious NYC drug lord on the rebound after his release from Sing Sing. You also get to see him dance to Schooly D's ‘Saturday Night.’

‘It was like a message from God: “Honesty doesn't pay, sucker.”’

It’s not at all reductive to call Fernando Meirelles and Kátia Lund’s hyperkinetic crime saga ‘the Brazilian Goodfellas’, given its immersive narrative and decades-long sweep. But by nature of its setting – the slums of Rio – it tells a very different story, one where the socioeconomic conditions amp up the violence, the desperation and the visual energy. Meirelles and Lund bust out every cinematic trick in their bag, creating a film that shoots out the gate like a bullet and doesn’t relent for 130 minutes.

‘Hey you! Haircut! Where are you goin’?’

A movie to make you wish Gene Hackman came out of retirement, this frenetic, down-and-dirty crime film sees the actor as a no-bullshit NYC cop on the trail of some murky drug lords from France (nicknamed ‘Frog One’ and ‘Frog Two’).

Seijun Suzuki’s slick tale of a yakuza boss forced to wander Tokyo with assassins in hot pursuit is the end-all, be-all of hyper-stylised Japanese gangster flicks. Dripping with cool, Tokyo Drifter’s DNA is all over everything from Point Blank to the collected works of John Woo and Quentin Tarantino, yet nobody has matched it in the half century since it entered the cultural conversation. 

‘You know what I love? When characters you've long since forgotten in this great novel called life show up at the end and the whole story gets filled right in.’

This twisting Steven Soderbergh film is best described as a depiction of unorganized crime, depicting a ramshackle Detroit crew dealing with a job gone wrong. The super-wide angle cinematography is an acquired taste, but seeing Don Cheadle and Benicio del Toro portray complicated criminals trying to save their own hides is worth the trouble.

‘Listen, Little Boy, in this business there's only one law you gotta follow to keep out of trouble: Do it first, do it yourself, and keep on doing it.’

He may not have snorted quite as much cocaine as Tony Montana (who has?), but Antonio ‘Tony’ Camonte (Paul Muni) will always be the original Scarface. Howard Hawks and Richard Rosson’s formative gangster classic shocked the world with its lightly fictionalized take on how Al Capone Tommy-gunned his way to being king of Chicago.

‘You wanna play rough? Okay. Say hello to my little friend!’

The world is yours, Tony Montana, or at least our No. 29 slot is. Don't even begin to complain that Brian De Palma's dizzyingly lurid coke meltdown ranks higher than the 1932 original – it's proven to be vastly more influential, the throbbing id of many criminal fantasies since.

‘Warriors, come out to play-ay!’

About as realistic in its portrayal of street violence as Teenage Mutant Ninja Turtles, Walter Hill’s cult classic nonetheless functions as a gritty time capsule of unsanitised, pre-Giuliani New York. The plot is Greek odyssey meets ’80s arcade game: a crew of leather-vested bad dudes repping Coney Island are framed for the assassination of a rival gang leader, forcing them to fight through the night to clear their names. Beware the Baseball Furies!

‘Nothing is true; everything is permitted.’

‘A sociopathic gangster hides out in swinging London’ sounds like an Austin Powers sequel, but Nicolas Roeg’s psychedelic identity study is more like Persona on mushrooms. Mick Jagger is a reclusive rock star unwittingly harbouring a violent criminal (James Fox) at his flat. Initially at odds, the two grow so fascinated with each other’s divergent lifestyles that by the end, it’s hard to tell one from the other.

‘You don't understand. I coulda had class. I coulda been a contender. I coulda been somebody, instead of a bum, which is what I am, let’s face it.’

You can imagine On the Waterfront’s brazen Mob-adjacent teamster Johnny Friendly (Lee J Cobb) in a Scorsese movie, presiding over the New Jersey docks like a wannabe wiseguy. At least, until he gets whacked halfway through. Here, it’s Marlon Brando’s docker Terry Malloy who represents a form of bare-knuckled rough justice in Elia Kazan’s classic tale of human failings, bad choices and moral courage. 

‘I didn’t do nothing.’

John Singleton’s compassionate, alarming debut was a scary revelation for audiences drawn into the world of South Central Los Angeles and the life of Tre (Cuba Gooding Jr.), a young African-American man trying and failing to steer clear of the violent warfare between gangs that ruled the area.

‘Sit down and shut up, will ya? Try not to live up to all my expectations.’

It's better remembered for popularizing Scott Joplin's rags, but George Roy Hill's verbally deft comedy has staying power as a fun, double-crossing caper, gentler than most films on this list. Stars like Paul Newman and Robert Redford don't hurt the appeal one bit.

‘What thousands must die, so that Caesar may become the great.’

For our money, a superior thriller to Martin Scorsese’s remake The Departed, this classic slice of Hong Kong cinema has the cool AF Andy Lau and Tony Leung karmically connected in the city’s violent criminal underground. One’s an undercover cop, the other is an undercover triad member. The old adage about cops and crims being two sides of the same coin has rarely been this brilliantly realised on screen.

‘You wanna know how to get Capone? They pull a knife, you pull a gun. He sends one of yours to the hospital, you send one of his to the morgue.’

Here's some classy, Oscar-approved filmmaking from Brian De Palma, who marshals the true story of Eliot Ness's crusading Chicago cops to a felicitous pitch of character-driven action. The slow-motion baby carriage scene works great—and not just for geeks eager to drop a little Battleship Potemkin knowledge on their dates.

‘I always said he should burn in hell. But, hey, Chicago will do.’

This list is filled with movies that follow gangsters who meet untimely ends, but directors rarely devote much screentime to the people they leave behind. Steve McQueen's Chicago-set caper is centered around the widows of a recently-deceased criminal outfit, who band together to complete their husbands' unfinished business, attempting to pull off a dangeous heist.

‘You don't crucify people! Not on Good Friday.’

A sharp touch of timeliness gives this London gangster flick its power: Bob Hoskins’s Harold Shand finds himself at the center of a dangerous crime nexus, involving Republican Irish terrorists and the American Mafia – all in the shadow of the creeping, Thatcherite capitalist dream.

‘You have anything to say before I blow your brains out, you miserable prick?’

The first of three collaborations between David Cronenberg and Viggo Mortensen, this explosive thriller stars Mortensen as a diner owner who might not be the all-American small-town guy he appears to be. It's executed with Cronenberg's signature wit and bravura style.

‘One must choose: die…or lie?’

Director Jean-Pierre Melville would become a giant in the specialized field of the gangster film and this is one of his earliest triumphs, a beautiful showcase for rising star Jean-Paul Belmondo as a shifty informant. Cool and minimalist, Melville's style remains influential.

‘You're not the only one that had an unhappy childhood.’

The template for the modern heist movie was set by this brooding slice of French noir, as a gang of thieves plan to pull off the impossible by ripping off a jewelry store on the Rue de Rivoli.  The heart-stopping, near-wordless break-in scene remains unbeaten 60 years on.

‘Harry, do you know what you're doing? You're killing me. You're killing me and yourself.’

Before he set the bar for movie heists with 1955’s Rififi, Jules Dassin left his mark on the world of hustlers and con men with this unsympathetic portrait of London lowlifes desperate to make their next score. Every bit as dark as its title suggests, Night and the City follows American Harry Fabian (Richard Widmark) as he backs the wrong wrestler and learns there’s no escaping the underworld, only sinking deeper into it.

‘Sentimental value? Ah. I heard of that.’

There’s more to David Cronenberg’s full-throated gangster nightmare than just a bunch of naked dudes smacking each other in a sauna. This is a prescient examination of the Russian takeover of London, featuring a career-best turn from Viggo Mortensen as the taciturn, grimacing antihero.

‘We have to score, kill, and we need money. If not, you die, because you’re part of the war.’

A devastating, kaleidoscopic portrait of modern-day crime in southern Italy, Gommorrah became an instant classic upon release and even spawned a five-season Italian series. Director Matteo Garrone dramatized real-world corruption (along with well-armed teens acting out Scarface) and still managed to stay alive.

‘Zed’s dead, baby.’

Quentin Tarantino’s legacy-cementing masterwork drinks from the fountain of eternal cool. It’s the defining movie of the ’90s, but it’s not stuck there, or in any particular decade – when the aliens descend to pick over the remains of our climate-ravaged planet, they’ll find a VHS copy of Pulp Fiction among the ruins and agree that Samuel L Jackson’s existentially exhausted hitman was the baddest motherfucker to ever walk the earth.

‘It's good to die fat as a pig.’

Seijun Suzuki spent years aggravating the execs at Nikkatsu studios with his hyper-idiosyncratic genre pictures, and this psychosexual pop-art thriller turned out to be the last straw. Cherub-faced Joe Shishido plays Goro Hanada, a hitman with a thing for the smell of boiling rice, who’s pushed into a battle of wits with the world’s top-ranked contract killer. As always with Suzuki, the story is merely a framework for the director’s existentialist musings and surrealist flights of fancy. It ended up getting him fired, but given the impact the movie had on the descendents like John Woo and Quentin Tarantino, it was worth it.  

‘But quite frankly your attitude appalls me. It's not what you're saying. It's all this stuff you're not saying. Insinnuendos.’

Movies about ageing criminals getting coaxed into one last job were a trope long before Al Pacino’s ‘Just when I thought I was out, they pull me back in’ bit, but Jonathan Glazer’s darkly comic thriller has a style, tone and language all its own. Much of the attention went to Ben Kingsley’s turn as a foul-mouthed loose cannon trying to push Ray Winstone’s happily retired gangster back into the game, and rightly so. But everyone is really facking great, including Ian McShane as the crime boss who won’t take ‘no’ for an answer.

‘One thing I always try to teach my boys: Always put one in the brain.’

The Coen brothers’ spin on Prohibition-era gangster movies is all plot twists and double crosses, featuring fast, witty dialogue and knockout acting – especially from John Turturro as slippery Bernie Bernbaum, an operator who gets in over his hat.

‘You'll put up, and you'll shut up! You hear nothing, and you see nothing! Just like you did for Bugsy!’

Sergio Leone's Depression-era epic evokes New York City's teeming Lower East Side like no movie before or since. The curiosity of youth is balanced against the euphoria and bitter sacrifices of criminal life. More than just The Godfather of Jewish gangster movies, Leone's masterwork is the apex of a glorious, genre-bending career.

‘If history has taught us anything, it is that you can kill anyone.’

Known as cinema’s greatest sequel, this is such a monstrous beast of a movie that it makes the first installment feel like a short. The time-hopping structure allows Francis Ford Coppola to flesh out the Corleone’s world in violently fascinating new dimensions, yet somehow, the brutal drama of the original is sustained across half a century.

‘And they ain't gonna catch us. 'Cause I'm even better at runnin' than I am at robbin' banks!’

It’s not precisely self-evident watching through modern eyes, but Bonnie and Clyde didn’t just shock ’60s movie audiences, it changed the shape of Hollywood. Borrowing from the attitude and aesthetics of the French New Wave, it presented crime’s most famous power couple – portrayed with smoldering chemistry by Warren Beatty and Faye Dunaway – not as menaces to society but heroes of the counterculture. Critics and studio execs clutched their pearls, but young viewers loved it, and the American film industry spent the next decade telling stories steeped in moral ambiguity and blunt realism – although few achieved Bonnie and Clyde’s level of sheer cool. 

‘$20? Let’s go to the movies!’

The giddy, streetwise flipside to the brooding austerity of The Godfather, Martin Scorsese’s breakthrough explores the grasping underside of the gangland dream. Harvey Keitel’s guilt-ridden Charlie is the heart of the film, but it’s Robert De Niro as firecracker Johnny Boy that you’ll remember.

‘Why can't we pick our own colors?’

Quentin Tarantino set the film scene on fire with this sparkling story of five criminals put together for a heist that goes wrong – each anonymously named after a color and each played by an actor as good as the next. Tarantino charts the bloody fallout with a savage wit, a masterly grip on storytelling and dialogue that’s still to die for, three decades later.

‘I'm funny how, I mean funny like I'm a clown, I amuse you? I make you laugh, I'm here to fuckin' amuse you?’

It might just be Martin Scorsese's finest two hours and change, this swirling, relentlessly paced crime classic that served up a feast of salty dialogue (we all have our favorite quotes) and, in turn, directly inspired both The Sopranos and Quentin Tarantino's on-the-horizon game-changers. It's not a stretch to call Goodfellas the most significant movie of the last 30 years. It's certainly the most fun.

‘Alright, sister, that's a mighty pretty head you got on your shoulders. You want to keep it there or start carrying it around in your hands?’

The best ‘one last job’ movie ever made, Stanley Kubrick’s third feature is a terse and nasty little noir about a career criminal (Sterling Hayden) who assembles a team for the racetrack heist that’s going to net him the dough he needs to get out of the game and marry his gal. Kubrick caps off the story with the kind of nihilistic panache that makes even the end of Dr. Strangelove feel like a happily-ever-after.

‘Leave the gun. Take the cannoli.’

The undisputed don of the gangster-flick family, Francis Ford Coppola’s timeless tragedy of twisted loyalty and moral decay refuses to become any less powerful or relevant. From its epic moments – the horse’s head in the bed, Luca Brasi’s bulging fish-eyes – to the most intimate details (Enzo the baker’s shaking hands, Clemenza’s spaghetti recipe), The Godfather never puts one immaculately crafted leather boot out of line. If we revisit this list in a century’s time, expect it to be holding steady in the top spot.