Top 10 Movie Portrayals of Real Life Gangsters

Script written by Tiffany Ezuma. You think you’re a tough guy? We’ll see about that. The movies are full of gangsters and made men, but our favorites are those based on a real guy who made his way up the mob ranks the hard way. In this video, WatchMojo.com as we count down our picks for the top 10 movie portrayals of real-life gangsters. For this list, we’ve chosen movie depictions of real-life criminals who were part of a gang – which means, those baddies who acted alone or as part of a twosome need not apply.
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Script written by Tiffany Ezuma.

Top 10 Movie Portrayals of Real Life Gangsters


You think you’re a tough guy? We’ll see about that. Welcome to WatchMojo.com, and today we’re counting down our picks for the top 10 movie portrayals of real-life gangsters.

For this list, we’ve chosen movie depictions of real-life criminals who were part of a gang – which means, those baddies who acted alone or as part of a twosome need not apply.

#10: Sean Penn as Mickey Cohen
“Gangster Squad” (2013)

While the stylized film itself was only so-so, Penn embodied the spirit of the ex-boxer turned gangster. As the main antagonist of the movie, every time he’s on-screen he’s a powder keg of emotion, often erupting at the slightest provocation. He’s loud, brash, and unwilling to back down even as the cops are closing in on him. Penn strikes a perfect balance between cocky and calculating when portraying this Jewish Mafia member and king of the Sunset Strip.

#9: Robert De Niro as Al Capone
“The Untouchables” (1987)

Rod Steiger’s depiction in the 1959 biopic was a complex, unglamorous portrayal of Capone; but leave it to De Niro to blow anyone else out of the water. Standing out in a film like this isn’t a cakewalk, with Billy Drago also giving a great performance as the real-life Frank Nitti. But De Niro is truly terrifying as this Prohibition-era criminal mastermind, using rough dialogue and a commanding nature to intimidate agent Eliot Ness, but also standing tall as a high-profile member of society.

#8: Tim Roth as Dutch Schultz
“Hoodlum” (1997)

There’s a toss-up in this film between Roth’s performance and Laurence Fishburne’s portrayal of Ellsworth “Bumpy” Johnson; but Roth edges him out. Even though Schultz is the associate of mob boss Lucky Luciano, it’s hard to believe this guy is taking orders from anyone. He’s wild on screen and there’s something about his character that’s slightly unhinged. It seems that Dutch is the one calling all the shots, as he orders hits and tries to double-cross his boss.

#7: Jack Nicholson as Jimmy Hoffa
“Hoffa” (1992)

Even though the movie only met with fair reviews, Nicholson perfectly embodies this larger-than-life Teamsters boss. Mostly told in flashbacks, it tells the story of how Hoffa came to be such a powerful political figure and enemy to JFK, among others. Nicholson is quietly menacing and it’s easy to tell he’s not someone to be messed with. He brings his trademark poker face to the role, making it impossible to guess what he’s thinking.

#6: Al Pacino as Benjamin “Lefty” Ruggiero
“Donnie Brasco” (1997)

Ruggiero would strictly be the bad guy in any other film but in this portrayal, his character is much more complex. His friendship with undercover agent, Donnie Brasco, shows that he’s more than a killer – he’s a low-on-the-totem-pole mafia man who’s been passed over for promotions and has a son at home who’s struggling with drug addiction. Pacino’s Ruggiero is a man with everyday problems; so it’s almost easy to understand why he does what he does.

#5: Warren Beatty as Benjamin “Bugsy” Siegel
“Bugsy” (1991)

When you’ve also portrayed the iconic Clyde Barrow, playing the tough guy starts to come naturally. At least that’s the case with Beatty when he depicts mobster-turned-hotelier-turned Vegas big shot, Bugsy Siegel. Beatty plays Bugsy as a man with vision others can’t see, who decides to start a hotel casino in the desolate terrain of Las Vegas. He’s a complicated man, trying to keep the love of his woman while gambling on their future. But that doesn’t make him soft!

#4: Daniel Day-Lewis as Bill “the Butcher” Cutting
“Gangs of New York” (2002)

Day-Lewis is one of those actors that completely transform himself on-screen, and he’s almost unrecognizable as the Butcher. His demeanor is completely changed, and he comes across as a caged animal – ready to attack at any moment, and his best scenes are when he’s doing his worst. Though the character is not exactly a true-to-history portrayal of the real Bill the Butcher, whose family name was Poole not Cutting, the role still earned Day-Lewis the third Oscar nod of his career.

#3: Robert De Niro as Sam “Ace” Rothstein
“Casino” (1995)

In his second spot on our list, De Niro displays again that he and his “GoodFellas” co-star Joe Pesci have great chemistry as they portray business partners in the Las Vegas casino industry. As a gambling handicapper, De Niro depicts Rothstein as someone calculating, methodical, and more conservative than his partner. Sam doesn’t let anything slide past him though, and his attention to detail leaves him as the only one unscathed.

#2: Denzel Washington as Frank Lucas
“American Gangster” (2007)

As Harlem heroin dealer-turned-kingpin Frank Lucas, Washington gives one of the strongest performances of his career. He takes Lucas’s Scarface-like tale, and paints it as the classic American success story of working hard to achieve your dreams. But in his case, working hard means hiding heroin underneath the coffins of soldiers on their way back from Vietnam. The movie may have fictionalized some aspects of Lucas’ life but every bit of this performance is believable.

Before we let our number one pick outta the slammer, here are a few honorable mentions:
- Tom Hardy as Forrest Bondurant “Lawless” (2012)
- Cliff Curtis as Pablo Escobar “Blow” (2001)
- Delroy Lindo as West Indian Archie “Malcolm X” (1992)
- Eric Bogosian as Eddie Nash “Wonderland” (2003)

#1: Ray Liotta as Henry Hill
“GoodFellas” (1990)

He’s the man who became an FBI informant and helped take down fifty of his mob pals, and it’s Liotta’s depiction of Hill as an outsider that makes this performance so memorable. Viewers sympathize with this man who grew up in the Mafia culture and proudly proclaims at the beginning of the film: “As far back as I can remember, I always wanted to be a gangster.” Even the real-life Hill praised Liotta’s performance, often appearing in the media in support of the film. We don’t wanna know what he woulda done had he not liked it…

Do you agree with our list? Which gangster seemed real to you? For more tough-guy Top 10s published daily, be sure to subscribe to WatchMojo.com.
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