The 25 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. 

ABOUT THE AUTHOR

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

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