The best gangster movies to make you question your morals

Genres come and go, but gangster movies never go away. From the black and white era to the 3D, these morally bankrupt murderous mobsters with their own codes of honour have held a fascination for audiences. The guns, the suits, the power struggles, the bonds, the betrayals and, most of all, the unfettered violence have made gangsters and the cinema perfect partners in crime. Class directors like Howard Hawks, Francis Ford Coppola and Scorsese have elevated the genre way above its exploitative roots, and here are some of the greatest gangster flicks to seek out.

25. Infernal Affairs (2002) 

This Hong Kong classic is so good, Scorsese remade it without bettering it. Andrew Lau and Alan Maks' original two-mole thriller inspired The Departed, but Tony Leung and Andy Lau's cop-crook tango throws deeper, darker, deadlier shapes than Damon and DiCaprio's double act. Originally, the movie was heavily inspired by Face/Off, but those Woo-vian bullet ballets were ditched for the psychological stylings of a straight-up urban thriller. Quite a good job, really. There's no other movie quite like it. I mean, come on, that rooftop face-off? Okay, so there's still a bit of Woo's influence.

24. King of New York (1990) 

Dark and nihilistic, King Of New York sears into the memory. That's mainly down to Christopher Walken's turn as Frank White, a paper rich but spiritually bankrupt mob boss back from the Sing Sing grave to rebuild his drugs empire. It's the weird and eccentric schtick that Walken brings to this thuggish kingpin that makes the movie still have such an impact today. Roaming the streets of the Bronx in his stretch-limo hearse, White is New York City's Nosferatu, sucking the life from the city's veins. It's one of his most underseen performances - and one of his best. As Walken says himself, "when I go to an airport, all the cops, that's the movie they know."

23. Sonatine (1993)

Takeshi Kitano's minimalist hitman-in-hiding movie is a brave entry in the gangster canon. It leans on the philosophical side of the job, in an understated but poignant way. He stars in the movie as Murakawa, a Yakuza enforcer dispatched to investigate two sparring clans, only later realising it was an ambush.As a director, Kitano takes quite a few risks with style. That climactic shoot-out filmed from outside, shown only as a light show? The work of pure genius. Having a bunch of thugs clown around on a beach? Sounds a bit Tarantino-esque. It's things like that which got Kitano and the movie noticed in the international film world, earning him legions of loyal fans.

22. The Killing (1956)

Can't do the time, don't do the crime. Kubrick's racetrack stick-up unfolds in flashbacks, its storytelling splintered into pieces that really helps to nail the fatalistic theme. The movie revolves around a motley crew of crooks who team up for One Last Job. We all know how that typically goes.A crime film, said the director, is almost like a bullfight; it has a ritual and a pattern, which pretty much guarantees that the criminal isn't going to make it. As the movie jumps from Sterling Hayden's perfectly planned heist to the aftermath, his cool professionalism comes undone by the gang of squealers and bunglers he's working with. Sound familiar? Tarantino nicked ideas from the movie for Reservoir Dogs, boasting, this movie is my The Killing.

21. Carlito's Way (1993) 

"What might have been if Carlito's Way had forged new ground and not gone down smokin' in the shadow of Scarface?" wondered Rolling Stone magazine about Brian De Palma's mesmeric gangster flick. These days you have to wonder what the Stone guys were smoking not to see the neo-noir clout in the tale of mobster Carlito Brigante (Al Pacino) and his struggle to carve out a law-abiding life for himself. Even without Sean Penn's turn as a coke-hoovering shyster, this is scintillating stuff, from its dying man's voiceover to its bone-cracking violence. 

20. Get Carter (1971) 

It's grim up north. It's even grimmer when East End gangster Jack Carter (Michael Caine) arrives in Newcastle looking for the bloke who supposedly killed his brother. He meets with a local kingpin and starts leaving a trail of bodies behind him, as he desperately seeks justice. Nice and fluffy Michael Caine, this ain't. Get Carter injects the Brit-flick gangster movie with knuckle-scraping brutality. It's a hard-boiled flick that attracted its star due to the realistic portrayal of violence: director Mike Hodges shows that in real life, each punch grinds some teeth in, and just one thrust of the knife can open someone's heart. 

19. Gomorrah (2008) 

Gomorra won the Grand Prix at the Cannes Film Festival, and was selected as Italy’s official entry into the 2009 Academy Awards for Best Foreign Film. It's not hard to see why this grungy gangster flick caused such waves at the time of release. Set in the grubby Neapolitan underworld, it taps into the dangerous, violent world of the Camorra crime syndicate, who make a living moving cocaine. Shot in a lo-fi documentary style, director Matteo Garrone borrows a lot of style tips from the Italian neo-realists (c'mon, you've got to have seen The Bicycle Thief!) with naturalistic lighting, untrained actors and slow, real-time pacing. It makes you really feel like you're eavesdropping on a bunch of brutal thugs.

18. The Killer (1989) 

Chow Yun-Fat seeks bloody redemption in John Woo's seminal actioner, his Hong Kong hitman showing a twisted nobility as he takes on one last job to prevent the girl he injured from losing her sight. And then he winds up blind-sided by his boss, who double crosses him at the last second. "The killer wants to be good," the director reveals. "He's fed up with killing and he's trying to stop. The problem is, once you pick up a gun its hard to put down..."The Killer was slammed at home for glamourising the Triads, but had a much better reception abroad, launching the international careers of both star and director.

17. John Wick (2014) 

The movie that single-handedly relaunched Keanu Reeves' career, John Wick isn't just a gangster movie. It's loads of things. A blistering revenge tale, a tearjerker that tugs on the heart strings, and a bloody actioner. Best of all, it's free of clutter. There's no uneccessary subplots brought in to pad out the running time. The plot moves along nicely, with action focused solely on Wick's mission to wipe out Reek. Sorry, the son of a Russian mob boss played by the guy who plays Reek. He just happens to take out a few of his wannabe-gangstah chums along the way. Director Chad Stahelski proves his time spent on Hollywood sets as a stunt choreographer paid off - this is how you execute a perfect mix of thrills and action. The nightclub scene alone is pure cinematic gold.

16. City of God (2002) 

Ferociously kinetic, Fernando Meirelles and co-director Ktia Lund's adaptation of Paolo Lin's non-fiction epic is also propelled by a righteous social agenda.The film rips through three decades of urban deterioration and criminal expansion in the Rio De Janeiro slums - the favelas. It starts with a blackly comic catch-that-chicken scene, flips to the 60s and then forwards to the 80s via turf wars and the drug-terror tactics of one mean cat, Lil Ze.Meirelles and Lund spin mood on a dime, orchestrating the action around a total lack of morality. There's nothing and no-one in these sun-kissed backstreets that's immune to the horrors of this street-turf war. God, you suspect, is dead.


Gem is GR+'s west coast entertainment news reporter. She’s a bit obsessed with all things Aliens and Terminator.


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