The 15 Best Portrayals of Real-Life Gangsters in Movies

Will Sean Penn's turn as Mickey Cohen in Gangster Squad rival these dynamite performances? It's a tall order.

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Complex Original

Image via Complex Original

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In terms of American crime history, Mickey Cohen never receives the same widespread notoriety of a Jesse James or an Al Capone. Los Angeles historians, however, know all about the Brooklyn-born thug's legacy. After bouncing around from Chicago (where he briefly chopped it up with Capone) to Cleveland, the Jewish troublemaker settled down in L.A. in the late 1940s, where he was assigned by higher-up criminals Meyer Lansky and Lou Rothkopf to keep tabs on their associate Bugsy Siegel. There, in the City of Angels, Cohen truly came of age, upping his murder count, power status, and reputation so much that a group of cops and detectives ignored their profession's rules in order to take Cohen and his men out. Or at least try to.

The LAPD's law-breaking pursuit of Cohen provides the basis for Gangster Squad, the new highly stylized, star-packed action-crime film from director Ruben Fleischer (Zombieland, 30 Minutes or Less). In theaters nationwide this Friday, Gangster Squad features actors like Josh Brolin, Ryan Gosling, and Anthony Mackie playing the good guys. On the other end, there's Sean Penn as Mickey Cohen, with the two-time Academy Award-winning actor's face altered by makeup to more closely resemble Cohen's.

Based on Gangster Squad's trailers and commercials, it's clear that Penn—spouting braggadocios taunts, cold-hearted threats, and grimacing while firing weapons—is in entertainingly heightened form. But the jury is still out on whether he's as good as The 15 Best Portrayals of Real-Life Gangsters in Movies or not. As you'll see here, the pressure is definitely on him.

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Written by Matt Barone (@MBarone)

15. Johnny Depp as John Dillinger, Public Enemies (2009)

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14. Denzel Washington as Frank Lucas, American Gangster (2007)

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13. Eric Bogosian as Eddie Nash, Wonderland (2003)

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12. Delroy Lindo as West Indian Archie, Malcolm X (1992)

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11. Laurence Fishburne as Ellsworth "Bumpy" Johnson, Hoodlum (1997)

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10. Billy Drago as Frank Nitti, The Untouchables (1987)

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9. Stephen Graham as Baby Face Nelson, Public Enemies (2009)

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8. Tim Roth as Dutch Schultz, Hoodlum (1997)

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7. Cliff Curtis as Pablo Escobar, Blow (2001)

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6. Al Pacino as Benjamin "Lefty" Ruggiero, Donnie Brasco (1997)

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5. Vincent Cassel as Jacques Mesrine, Mesrine: Killer Instinct (2008) and Mesrine: Public Enemy #1 (2008)

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4. Warren Beatty as Clyde Barrow, Bonnie and Clyde (1967)

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3. Ray Liotta as Henry Hill, Goodfellas (1990)

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2. Daniel Day-Lewis as "Bill the Butcher," Gangs of New York (2002)

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1. Robert De Niro as Al Capone, The Untouchables (1987)

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