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Feature : 10 Best Movie Gangsters

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What do we love about a life of crime on screen? Is it ever as glamorous, thrilling, scary and full of intrigue in real life as it is on film? The life of a career organised criminal seems to capture everything we love about the movies, everything we wish we could be writ large – in control of everything around us, smiting enemies on a whim and enjoying all the privileges and perks of power. As one Henry Hill put it ‘as far back as I can remember, I always wanted to be a gangster’. Don’t we all?

1. Tony Montana (Scarface – 1983)

The mirror image of the American dream, Tony Montana’s life is a razor’s edge away from that of the entrepreneurs the American Way holds most dear. Substitute coke for web start-ups and guns for annual reports and you have a corporate success story for the ages. Like the archetypal hard working immigrant, Cuban lowlife Tony ruthlessly works his way up from nothing, rising out of the slums of a Miami tenement and amassing a drug empire and vast fortune with nothing but his word and his balls.

Choice line: ‘Look at dem Pelicangs fly’

2. Vito Corleone (The Godfather – 1972)

After a generation of Cagney-inspired, Americanised Mob pictures with Tommy Guns, garish shoes and snarls of ‘you dirty rat’, Vito Corleone is a respectable, well-dressed, highly principled businessman to his core. He makes his decisions with a clear head and goes about transferring his empire to his most competent son Michael with the precision of a military commander. Even the choice he offers to a producer of either his signature or his brains on a contract is a carefully crafted cost/benefit analysis. Not Brando’s signature role for nothing.

Choice line: ‘Is vengeance going to bring your son back to you? Or my boy to me?’

3. Leo O’Bannon (Miller’s Crossing – 1990)

He’s not the smartest prohibition-era crime boss, but Leo’s (Albert Finney) firmly on top, and the reason why is pure mettle. When two Thompson-wielding goons trudge up to his bedroom to whack him, Leo blows one away, escapes the burning house through a window and sticks around to make Swiss cheese of the other from the street. Even friends shouldn’t cross him – when trusted lieutenant Tom (Gabriel Byrne) thinks he’s leaving him in his office to cry quietly after admitting to seeing Leo’s girl Verna, he doesn’t expect Leo to come charging down the hall after him to kick his arse right down the stairs.

Choice line: ‘You ain’t got a license to kill bookies and today I ain’t sellin’. So take your flunky and dangle.’

4. Al Capone (The Untouchables – 1987)

It seems almost quaint that such corruption and violence centred around booze when the rackets of mobsters like Capone are legitimate leisure industries these days, but no heavy handed method was above the don of Chicago, from blowing a little girl to smithereens for being in the wrong place at the wrong time to caving in the head of an overly ambitious minion with a baseball bat at the dinner table. De Niro was at the top of his game, piling on weight and even wearing the same silk underwear the real Capone favoured. He plays Capone as a rambunctious media tart but, like a more brutal Vito Corleone, his every blood-soaked decision has an eye on the bottom line.

Choice line: ‘There is violence in Chicago, but not by me and not be anybody I employ, and I’ll tell you why – because it’s not good business.’

5. Brick Top (Snatch – 2000)

In London’s East End, you can’t swing a cat without hitting a whole host of unscrupulous racketeers, fixers and standover men, and in Snatch’s world of missing diamonds, indestructible Russian assassins and inept burglars, all Tommy (Stephen Graham) and Turkish (Jason Statham) have to avoid is the fearsome boxing promoter Brick Top (Alan Ford). Somewhere between your kindly old Uncle with his constant rhyming slang and Freddy Krueger with his penchant for dismembering the bodies of his enemies to feed his fighting pigs, every nice word that comes out of his quiet, hateful mouth is bitter irony. Like a rattlesnake, you rarely see Brick Top strike, but the danger and menace surround him like an aura. As Turkish explains early on, the one place you don’t want to be is in the pocket of Brick Top.

Choice line (after being offered sugar in his tea): ‘No thank you Turkish, I’m sweet enough.’

6. Marsellus Wallace (Pulp Fiction – 1994)

Like many of the most dangerous movie gangsters and creatures in the animal kingdom, we never see Marsellus Wallace (Ving Rhames) commit an act of violence. By contrast, we see the most terrible of acts committed upon him and still he scares us with his deadpan promise of ‘a pair of pliers and a blowtorch’. Slow and straight talking, when Wallace has something to say time stops until he’s delivered a signature monologue peppered with considered pauses. Until The Gold Watch, we never even see his face clearly, his instructions to boxer Butch (Bruce Willis) to throw the big match delivered while we stare at the back of his commanding black head.

Choice line: ‘In the fifth, your ass goes down. …Say it.’

7. Don Logan (Sexy Beast, 2000)

One of Ben Kingsley’s rare villains, Don Logan is a nightmare of pure id in Jonathan Glazer’s blistering black comedy. Kingsley isn’t tall or solidly built and his nasal cockney twang doesn’t exactly inspire terror. But his spiritual soul brother is Joe Pesci’s Tommy DeVito, an unhinged, loose cannon of destruction waiting for an excuse. Watch the fear and shame in Gal ‘Ray Winstone’, his wife and friends that they’re too terrified to tell Don to just shove off back to England because they’re retired from crime. Murder and terror waiting to happen.

Choice line: “I got to change my shirt, it’s sticking to me, I’m sweatin’ like a c__t.’

8. Li’l Ze (City of God – 2002)

The superlatives usually reserved for gangster movies (and you’ve already read several in this list) can be applied to the power of Fernando Meirelles’ epic of the life of Brazil’s favela drug gangs and still not sum it up. And the most effective part is Li’l Ze, as merciless and monstrous a killer when he’s just a little kid as when he’s a twentysomething gang leader. If watching him laugh as he methodically shoots the hotel staff his friends have tied up before knocking the place over doesn’t convince you of the benefits of forced sterilisation, nothing will.

Choice line (to a young boy): ‘Where do you want to take the shot? In the hand or in the foot?’

9. Henry Hill (Goodfellas – 1990)

In the academic world of film theory, Henry Hill (Ray Liotta) is us, the audience, living our fantasy of mobster life through his exposition of it. We’ve grown up seeing the glamour, the riches, the good lives of wise guys. Many of Hill’s voiceover monologues in Martin Scorsese’s searing story of Mob culture speak of the spoils of organised crime – the parties, the open doors, the best tables at every club. And who’d want to give it up? For he and his friend, Hill says, to live any other way was nuts. Sure the paranoia of drug pushing, threat of murder by your closest friends and boring life under witness protection was the only future, but what a ride…

Choice line: ‘Whenever we needed money, we’d rob the airport’

10. Rico Bandello (Little Caesar – 1930)

The Golden Years of Hollywood meets the old school mobster in the era when they still held sway in everything from alcohol to prostitution. Until Coppola rewrote the rulebook 40 years later, Edward G Robinson’s portrayal of Rico was the template for all that followed. It’s almost comic book camp by today’s standards, and the sneered lines of ‘You’re hanging around with me, see?’ are a museum piece, but Robinson was everything we now feel about Vito Corleone during the pre- and post-war years.

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About Drew Turney

An Australian-based film critic and celebrity interviewer now based in Los Angeles, California.

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