The 15 Best Portrayals of Real-Life Gangsters in Movies

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)

The legacy of robber extraordinaire John Dillinger is a lofty one, notable for its stronghold on the public consciousness during his criminal reign as well as after. As newspaper readers and everyday men and women viewed him, he was an outlaw who could've starred in motion pictures if he'd chosen a different career path. Known for his good looks and his come-and-get-me confidence, Dillinger enjoyed the kind of celebrity status that'd have him on gossip blogs and National Enquirer covers today.

Thus, it's only right that director Michael Mann cast one of Hollywood's all-time great heartthrobs-with-talent, Johnny Depp, to play Dillinger in the uneven but ultimately riveting 2009 flick Public Enemies. It isn't necessarily Depp's best performance, nor is it particularly grandiose—he basically plays a heightened version of himself while holding a Tommy gun and wearing 1930s garb. But it's a refreshing and convincing reminder that Depp is incredibly charismatic, especially when he's not covered in elaborate makeup and hamming it up in a Tim Burton or Gore Verbinski movie.

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

The best thing about Flight, the recent Denzel Washington-starring drama about an alcoholic airplane pilot: Its immediate ability to remind us that he's a superior actor. That's not always the case with his ongoing string of stylized action movies (i.e., The Book of Eli, Safe House), in which Washington is typically solid but usually gives the impression of a proven actor taking the easy way out. In that sense, Flight has much in common with Ridley Scott's 2007 true-crime flick American Gangster.

Washington gives a powerhouse performance as Frank Lucas, a heroin dealer and organized crime kingpin who ran the streets of Harlem throughout the late 1960s and early '70s. American Gangster fictionalizes many aspects of Lucas' life, but it's nonetheless compelling, fast-paced, and home to numerous top-shelf actors at their best.

Playing Lucas as suave, determined, and bullshit-free, Washington conveys the aura of a less-tragic Tony Montana.

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

Wonderland—the sordid dramatization of porn star John Holmes' (Val Kilmer) involvement in a July 1981 quadruple homicide in Hollywood—is a sloppy, overblown movie housing several excellent performances, namely Eric Bogosian's turn as the ordeal's alleged mastermind, Eddie Nash.

Originally born in Palestine (as Adel Gharib Nasrallah), Nash rose to fame in Hollywood by owning various nightclubs and discos, and, in a much quieter fashion, dealing drugs and living the criminal lifestyle. It's said that the Wonderland Murders were payback from Nash after his house was robbed two days earlier (on a tip from his "friend" Holmes, who was indebted to the robbers).

Bogosian's performance is certainly one of Wonderland's showiest, blending a dangerous cult-leader-like charisma with the actor's own natural creepiness. With those large, piercing eyes, Bogosian intimidates by merely waking up in the morning.

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

Spike Lee's towering 1992 biopic Malcolm X is a mesmerizing showcase for star Denzel Washington. Both Lee and Washington delivered their best work—Lee, to his credit, also co-wrote the film's sprawling, meticulously layered screenplay (with Arnold Perl), adapting The Autobiography of Malcolm X.

One of the screenplay's (and, in turn, the movie's) most fascinating sections comes early on, when a younger Malcolm Little (who'd eventually replace the Little with X when he joined the Nation of Islam) is a hotshot, zoot-suit-wearing criminal soaking up guidance from numbers-running Harlem gangster West Indian Archie (Delroy Lindo). It's a small role, but Lindo—who'd return to the Spike Lee business with an even better performance in the 1995 film Clockers—nails Archie's enviable but untrustworthy swag with real panache, as well as his mental deterioration later in life.

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

On the whole, director Bill Duke's talk-heavy Hoodlum isn't an entirely exciting gangster flick. It's far too concerned with expository conversations and wrongfully impartial to action, relying on its game cast to carry the whole weight. Fortunately, Laurence Fishburne brought his A-game as Ellsworth "Bumpy" Johnson.

Running things in Harlem, Johnson started off working under illegal lottery (or "numbers") impresario Madame Stephanie St. Clair, earning the neighborhood's respect at the young age of 27 by conducting fruitful, cordial business with the Italian Mafia. In Hoodlum, Fishburne portrays Johnson during his rise to infamy under the guidance St. Claire (Cicely Tyson) and against opposition from aspiring racketeers Lucky Luciano (Andy Garcia) and Dutch Schultz (Tim Roth).

Fishburne's performance is all in-command coolness, with Johnson making a name for himself by keeping a level head and besting foes with smarts more so than brawn.

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

As Al Capone's righthand man Frank Nitti in Brian De Palma's The Untouchables, character actor Billy Drago makes for a very formidable enforcer. He's the Chicago crime outfit's deadliest gun, the enforcer that Capone tasks with unloading multiple Tommy gun bullets into elder officer Jim Malone (Sean Connery) in one of the movie's better sequences, as well as killing a police-protected snitch in a precinct. And Drago—a slithery, skeletal-looking presence who's able to induce fear more through creepiness than physical intimidation—owns the role.

Interestingly, however, Drago's version of Nitti isn't all that much like the real version. Using some creative license, screenwriter David Mamet changed Nitti's story quite a bit for the film's benefit. In reality, Nitti handled Capone's financial pursuits, not his body-dropping assignments. For those tasks, Capone was more likely to call upon Fred Burke or Jack McGurn.

And when Drago's Nitti dies from Ness pushing him off of a rooftop, that's just Mamet providing a satisfying, good-conquers-evil conclusion—really, Nitti ran Capone's operation for six years after the latter's death, before committing suicide in 1943 to avoid a potential jail sentence.

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

New rule: Moving forward, any mob and/or gangster movie or TV show must include British actor Stephen Graham. Need convincing as to why? Catch up with HBO's Boardwalk Empire, which features Graham killing it as Al Capone, playing the infamous criminal as a combustible tough guy who conceals an underlying, family-triggered softness.

And, wouldn't you know it, Graham's work on Boardwalk Empire isn't a one-shot deal. In Michael Mann's John Dillinger (Johnny Depp) versus Melvin Purvis (Christian Bale) flick Public Enemies, Graham beasts out as Baby Face Nelson, Dillinger's craziest associate. Like the real-life gangster he portrays, Graham's performance is a study in contrast: He looks harmless enough, but give him a gun and as much as a side eye and he'll murder you with unbridled, easily detectable pleasure.

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

As previously mentioned in regards to Laurence Fishburne's strong performance, the 1997 gangster flick Hoodlum is, at times, a verbose slog, one devoid of a sufficient amount of energy. Whenever Hoodlum does liven up, though, it's most likely due to the scene-stealing presence of Tim Roth. Playing Lucky Luciano's (Andy Garcia) right-hand man, Dutch Schultz, Roth tears through the film with menacing unpredictability.

At any given moment, Roth is able to provide a jolt with either a deadly threat or murderous act, but, at the same time, he's a joy to watch. Similar to Heath Ledger in The Dark Knight, but on a much lesser scale, he's so good that you sit around anticipating his next scene whenever he leaves the frame.

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

It's no small order to find an actor capable of playing Pablo Escobar—after all, he's one of history's most well-known and mythologized drug lords. Wisely, when casting the 2001 George Jung biopic (starring Johnny Depp) Blow, director Ted Demme and his colleagues opted away from big-name actors, any of whom would've taken audiences out of the picture. Imagine trying to buy that you're seeing Escobar at work if the Colombian cocaine trafficker is being portrayed by George Clooney or Liam Neeson.

In actor Cliff Curtis, the filmmakers found a relatively unknown performer who both resembled a younger Escobar and could legitimately command the screen. Which was crucial, since Escobar's scenes in Blow depict him as the criminal leader that he was, and, furthermore, quietly scary.

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

You can't help but feel for Benjamin "Lefty" Ruggiero in director Mike Newell's 1997 mob drama Donnie Brasco. A 30-year wiseguy, he's never been able to rise above being the Bonanno crime family's go-to hit man, and, at home, his son is addicted to drugs and his personal finances aren't up to snuff.

When FBI agent Joseph Pistone (Johnny Depp) goes undercover to smoke out the Bonanno crew, he quickly takes a liking to the sympathetic, seasoned Ruggiero. Their friendship anchors the film and lends it a tragic energy, since, once Pistone finishes his job, Ruggiero's world will go from undesirable to decimated.

Always so damn good playing louder, larger-than-life characters, Pacino is just as masterfully efficient when he tones it down. As Lefty Ruggiero, he's able to generate empathy for a Cosa Nostra member who, you know, has killed over 20 people in his lifetime.

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

If not for director Jean-Francois Richet's pair of excellent Mesrine movies back in 2008, stateside true crime buffs might still be unaware of Jacques Mesrine's story, and that'd be, well, criminal. Regarded as France's most notorious criminal, "The Man of a Hundred Faces" (as he was called due to his penchant for disguises) lived for the spotlight, using the aforementioned get-ups to move about in broad daylight even though he was a wanted criminal. Not to mention, the fame-lover always kept a hot chick by his side whenever he wasn't robbing banks, busting guns, or kidnapping people.

When it comes to French actors, very few are better than Vincent Cassel, so give Richet a hand for casting the country's premier thespian as Mesrine. In both Mesrine: Killer Instinct and Mesrine: Public Enemy #1, Cassel dominates every single frame, chewing through scenery and seemingly having the time of his life playing Mesrine with a cocksure swagger that's frequently offset by explosive violence. He's always threatening but never unappealing, strutting around like he runs the world but can also destroy it whenever he sees fit.

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

Bonnie Parker and Clyde Barrow—better known, simply, as Bonnie and Clyde—helped to romanticize the criminal lifestyle without doing so intentionally. Clyde was the head of the "Barrow Gang," a gun-toting crew that, between 1931 and 1934, robbed banks, inconspicuous stores, and gas stations, killing several people in the process. Bonnie, meanwhile, is said to have hardly ever taken part in any of the gunplay, despite the media's depiction of her as Clyde's equally badass partner-in-crime after their police-executed assassination on May 23, 1934.

Their public romanticism came from photos discovered inside the couple's Joplin, MO, hideout, that showed Bonnie and Clyde embracing each other and showing love against an illegal backdrop. And it was those photos that fueled director Arthur Penn's classic 1967 film Bonnie and Clyde, starring the gorgeous Faye Dunaway and the debonair Warren Beatty.

Back in the 1960s and '70s, actors didn't come any more handsome, revered, and heartthrob-ish than Mr. Beatty, so he was the perfect choice to embody Clyde Barrow with likability, charm, and a sexiness that'd make audiences root for him and leave them saddened once he and Dunaway's Bonnie get pummeled by dozens of bullets. It's one of the best "movie star" performances from a true Hollywood icon.

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

He's the orator of the immortal opening lines from master director Martin Scorsese's Goodfellas, arguably the greatest mobster movie ever made: "As far back as I can remember, I always wanted to be a gangster." And that's exactly what Henry Hill (Ray Liotta) became, working his way into the operation ran by Irishman Jimmy Conway (Robert De Niro, playing a character based on real-life criminal Jimmy Burke), an associate of mob boss Paul Cicero (Paul Sorvino, who's role was based on Paul Vario).

Unlike the other gangsters on this list, Henry Hill is seen in Goodfellas as a vulnerable, at times scared regular guy who joined the mob more for idol worship (he grew up in awe of the local Lucchese crime family in East New York, Brooklyn) than sheer bloodlust. As played by Liotta, he's no pushover, either, evidenced by a scene in which he nearly beats a guy to death for messing with his girlfriend (Lorraine Bracco).

Mostly, though, Hill serves as the audience's conduit, watching in both horror and wonderment as his associates, namely hot-headed Tommy DeVito (Joe Pesci, who's character is based on Thomas DeSimone), kill and brutalize like it's nothing. It comes as no surprise—aside from the fact that Goodfellas is based on Nicholas Pileggi's non-fiction book Wiseguy, about Hill's life—Hill eventually sells Conway out to the FBI and heads into the Witness Protection Program to save his and his family's asses.

Hill "always wanted to be a gangster," but, as sold wonderfully by Liotta, he wasn't entirely built for it.

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

In Steven Spielberg's Lincoln, Daniel Day-Lewis, per usual, gives a gargantuan performance our nation's 16th president, but there's something missing, something that's there in There Will be Blood and Gangs of New York. That thing: maniacal ruthlessness.

In our opinion, Day-Lewis at his best when he's being ferocious, and in Martin Scorsese's mid-19th-century-set epic Gangs of New York, his work as the cold-blooded, bloodthirsty crime overseer Bill the Butcher (based on Bowery Boys leader William Poole) is madness personified. The actor snarls and roars his way through a role that's equal parts magnetic and repulsive.

His dynamic evilness manifests itself greatly in a scene where the Butcher tosses a knife at underling Amsterdam Vallon (Leonardo Dicaprio) and beats the shit out of him, leaving him a bloody mess and with the parting words that he'll let Amsterdam live as a "freak worthy of Barnum's museum of wonders."

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

Playing the notorious Chicago crime lord Al Capone should be any actor's dream role. Not the biggest man in any room, Alphonse Gabriel Capone made up for his somewhat diminutive stature by always being the meanest, coldest, most ruthless gangster around (see: the 1927 Saint Valentine's Day Massacre). That was just amongst his illegally minded peers, though. To the public, he was a Robin Hood of sorts, using his dirty money to assist various charities.

It's a complicated acting assignment, no doubt, and in the 1987 Brian De Palma film The Untouchables, Robert De Niro killed the role in a monstrous, effectively sinister performance. Mixing charm with malice, De Niro's Capone sells icy dialogue like, about Treasury Department agent Eliot Ness (Kevin Costner), "I want you to get this fuck where he lives! I want his house burned to the ground! I wanna go there in the middle of the night and I wanna piss on his ashes!"

Capone's most memorable scene in The Untouchables involves a baseball bat, which he uses to bash a fellow mobster's head in, a moment inspired by a real-life 1929 incident where Capone bludgeoned three gangsters (John Scalise, Albert Anselmi, and Joseph "Hop Toad" Giunta) to death.

Fun method acting fact: In order to fully immerse himself in the role, De Niro always wore the same old-styled silk underwear that Capone wore. Hey, at least he was comfortable while going all Josh Hamilton on folks.