Sean Penn, Johnny Depp & More: Actors as Real-Life Gangsters (Photos)

Gangster Squad stars Sean Penn in the role of real-life 1940s mob kingpin Mickey Cohen. From Johnny Depp’s John Dillinger to Steve Buscemi’s Nucky Thompson on HBO’s Boardwalk Empire, see other real mobsters behind the characters.

Gangster Squad stars Sean Penn in the role of real-life 1940s mob kingpin Mickey Cohen. From Johnny Depp’s John Dillinger to Steve Buscemi’s Nucky Thompson on HBO’s Boardwalk Empire, see other real mobsters behind the characters.

Ryan Gosling’s Mom Borrows Eva Mendes’s Clothes; Beck Stars in Ads for Saint Laurent
The World According to Sean Penn
‘Gangster Squad’ Pushed Back

Warner Bros/AP

Sean Penn/Mickey Cohen

Sean Penn portrayed the mob boss of all mob bosses—Los Angeles–based Meyer Harris “Mickey” Cohen—in the latest pulp crime flick, Gangster Squad. Cohen was no stranger to dealings with other notorious gangsters, at times joining forces with Bugsy Siegel and Al Capone during his career and eventually becoming the West Coast strong-arm extension for the East Coast syndicate during the 1940s and 1950s.


Robert De Niro/Lefty Rosenthal

Deeply involved in Las Vegas organized crime, Frank “Lefty” Rosenthal was the real-life mobster portrayed in Martin Scorsese’s 1995 film Casino, which starred Robert De Niro and Joe Pesci.


Steve Buscemi/Nucky Johnson

Enoch Lewis “Nucky” Johnson became a household name when Steve Buscemi started playing him in the popular HBO drama, Boardwalk Empire. Taking advantage of the public’s desire for liquor during the Prohibition-era 1920s, Johnson ruled over Atlantic City as a venal city treasurer and bootlegger. But how true to life is Buscemi’s Nucky? “I don’t feel compelled to accurately portray the real person,” said Buscemi in an HBO Q&A, “but rather a corrupt political boss of that era.”


Jack Nicholson/Whitey Bulger

Martin Scorsese’s The Departed swept the 2007 Academy Awards, winning an Oscar for Best Picture. The film—based on Andrew Lau and Alan Mak’s 2002 Hong Kong film Infernal Affairs—stars Leonardo DiCaprio, Matt Damon, and Jack Nicholson, who plays organized-crime lord Frank Costello, said to be loosely based on James Joseph “Whitey” Bulger. In a life-is-stranger-than-fiction story involving FBI informants, drug trafficking, and racketeering, Bulger seemingly pulled a vanishing act and was the subject of a national manhunt beginning in 1995. He was arrested in 2011 in Santa Monica, Calif., and awaits trial for a string of murders that took place during the 1970s and 1980s.


Johnny Depp/John Dillinger

In the 2009 shoot-’em-up crime drama Public Enemies, Johnny Depp played notorious bank robber John Dillinger as a mysterious, violent hustler with a colorful personality. A product of the Great Depression, Dillinger robbed a dozen banks and was killed at age 31 after a bloody shootout. After serving time in the Indiana State Prison, Dillinger was quoted as saying, “I will be the meanest bastard you ever saw when I get out of here.”


Johnny Depp/Joseph Pistone (a.k.a. Donnie Brasco)

Sporting a killer mustache in 1970s-era crime drama Donnie Brasco, Johnny Depp plays undercover agent Joseph Pistone, who infiltrated and took down the Bonanno crime family in New York City while operating under the alias Donnie Brasco. While Pistone is a fictional construct, the longer Brasco stayed undercover, the more he feared he was becoming a mobster himself. In an interview with National Geographic in 2005, the FBI legend said he still travels in disguise due to a mob contract on his head.


Charles Bronson/Machine Gun Kelly

Before Charles Bronson was in Death Wish, he was generating fear as the titular notorious bank robber in Machine Gun Kelly in 1958. A Prohibition-era thug, George Celino Barnes fittingly chose his nickname after his favorite weapon. After a slew of offenses ranging from racketeering to kidnapping, he spent the rest of his years behind bars in Alcatraz.


Robert De Niro/Jimmy the Gent

Best known for raking in millions from the Lufthansa heist in 1978, James “Jimmy the Gent” Burke was associated with the Lucchese crime family. His story was said to be the inspiration for Jimmy Conway, Robert De Niro’s character in Goodfellas.


Denzel Washington/Frank Lucas

A Manhattan heroin drug lord in the 1970s, Frank Lucas rose from humble limo driver to powerful kingpin. His story was portrayed by Denzel Washington in the 2007 film American Gangster. Lucas was released from prison in 1991.


Faye Dunaway and Warren Beatty/Bonnie and Clyde

With a hankering for stolen cars, bank robberies, and bloody shootouts, these criminal lovebirds were charismatically played by Warren Beatty and Faye Dunaway in the 1967 film. Despite their cinematic (and notorious) mad love, their larcenous hijinks ended in 1934, when they were shot to death by police in Louisiana.


Robert De Niro/Al Capone

No stranger to intense mobster roles, Robert De Niro played fearsome crime-syndicate boss Al Capone in director Brian De Palma’s 1987 film, The Untouchables. The legendary Prohibition-era mobster—who has also been played by Rod Steiger, Jason Robards, Ben Gazzara, William Forsythe, F. Murray Abraham, and William Devane, as well as currently by Stephen Graham on HBO’s Boardwalk Empire—spent the later years of his life ill from contracting syphilis, and his name now synonymous with the Mafia.


Ray Liotta/Henry Hill

An unusual story of gangster turned FBI informant, Henry Hill of the Lucchese crime family—immortalized by Ray Liotta in the 1990 movie Goodfellas—died in June 2012. His story was chronicled in Nicholas Pileggi’s book Wise Guy: Life in a Mafia Family. Following Hill’s death, Liotta said of him, “Although I played Henry Hill in the movie Goodfellas, I only met him a few short times, so I can’t say I knew him, but I do know he lived a complicated life.”