25 Best Movie Portrayals Of Real Life Gangsters

Posted by , Updated on March 23, 2024

Real-life gangster movies pretty much write themselves. By taking the true story of a gangster and fitting it into a Hollywood box, studios have box office gold. From Goodfellas to The Departed, real-life gangster films know how to draw a crowd just by the intrigue that surrounds them. They’re tense, brutal, and fun to watch. But who has played some of the notorious criminals in history? Here are 25 Best Movie Portrayals Of Real Life Gangsters.



Vincent Cassel as Jacques Mesrine

Vincent_CasselSource: https://tribecafilm.com

In the movie Public Enemy #1, Vincent Cassel gave an electrifying performance as the notorious mobster Jacques Mesrine, made famous for his ingenious disguises, bank robberies, and prison break outs.


Delroy Lindo as West Indian Archie

Delroy_LindoSource: https://www.youtube.com/watch?v=KeNo70ICgVI

In Spike Lee’s biopic Malcolm X, Delroy Lindo had a small role as West Indian Archie. He ultimately gave a powerful performance of an intimidating and charming gangster who knows the streets of Harlem like the back of his hand.


Billy Drago as Frank Nitti

billy dragoSource: http://articles.chicagotribune.com

In Untouchables, Billy Drago played Frank Nitti, the man who would succeed Al Capone of the Chicago mob. In the movie, Drago played a quiet, cold, and intimidating figure, almost like a boogie man. However, he didn’t meet his demise by being thrown off a building by Eliot Ness like it shows in the movie, rather, he shot himself when he became a pariah.


Stephen Graham as Baby Face Nelson

stephen grahamSource: http://www.shortlist.com

In Michael Mann’s Public Enemies, Stephen Graham played Baby Face Nelson, one of John Dillinger’s partners who helped him escape prison. Graham gave a solid performance and was called the “British Joe Pesci” by Martin Scorcese.


Tim Roth as Dutch Schultz

Tim_RothSource: http://www.imdb.com/title/tt0119311/

Tim Roth usually knocks any role he’s given out of the park; his performance as Dutch Schutlz in the film Hoodlums was no exception. While Hoodlums wasn’t a great movie overall, Roth gave a menacing and electrifying performance as Schultz.


Laurence Fishburne as Ellsworth "Bumpy" Johnson

laurence fishburneSource: http://www.imdb.com/title/tt0119311/

Speaking of Hoodlum, Laurence Fishburne shined as the mob boss Ellsworth “Bumpy” Johnson. A performance which would be an important precursor to his breakout role as Morpheus in The Matrix.


Cliff Curtis as Pablo Escobar

cliff curtisSource: https://www.youtube.com

Trying to portray Pablo Escobar isn’t something to take lightly. He was one of the scariest and most notorious drug lords in history. However, Cliff Curtis in the film Blow, pulled it off in spades, not only looking like Escobar but portraying a casual yet intimidating figure.


Mark Wahlberg as Daniel Lugo

mark wahlbergSource: http://www.miaminewtimes.com

Mark Wahlberg pumped a lot of iron to get into shape to look like the gangster Daniel Lugo in Pain & Gain. Though Daniel Lugo was more of the brains and Wahlberg played him like dumb brute, he still managed the charming smile and personality that Lugo was said to have in order to pull off his schemes.


James Cagney as Martin Snyder

james cagneySource: http://actoroscar.blogspot.com

In Love Me or Leave Me, James Cagney played the mob boss Martin Snyder. The role and his amazing performance lead to him winning an Academy Award for Best Actor.


Joe Pesci as Tommy DeVito

joe pesciSource: http://www.imdb.com

Tommy DeVito in Goodfellas, played by Joe Pesci, is based on the gangster Thomas DeSimone, also known as Tommy D.

Pesci’s brutal portrayal of the murderous gangster would propel him to winning best actor at the Academy Awards.


Johnny Depp as John Dillinger

johnny deppSource: http://www.imdb.com

Known his charismatic and eccentric performances and characters, Johnny Depp took on a more subdued role in Public Enemies as the infamous John Dillinger. Depp’s charming yet brutal portrayal of Dillinger carried the film.


Warren Beatty as Clyde Barrow

warren beattySource: http://www.imdb.com

Warren Beatty portrayed the ex-con Clyde Barrow in the Academy Award winning film Bonnie and Clyde. His performance garnered him a nomination for Best Actor, but his charm wasn’t enough to take the win. His co-star Faye Dunaway, however, did.


Denzel Washington as Frank Lucas

Denzel_WashingtonSource: http://www.historyvshollywood.com

Denzel Washington always brings the magic in any role he takes on. His cold, intimidating performance as Frank Lucas was no exception. While Russell Crowe played a solid foil to Washington’s character in American Gangster, it was Washington’s amazing acting that ultimately made the story interesting.


Wesley Snipes as Nino Brown

WesleysnipesSource: http://gangsterreport.com/

Arguably the best performance of his career, Wesley Snipes as Nino Brown in New Jack City portrayed an intelligent criminal out to play the game as he saw it in America. Nino Brown is based on the real gangster, B.J. Chambers.


Eric Bogosian as Eddie Nash

Eric BogosianSource: http://articles.chicagotribune.com

Wonderland isn’t the greatest movie, but Eric Bogosian’s portrayal of the mobster Eddie Nash is charismatic, terrifying, and largely creepy.


Sean Penn as Mickey Cohen

Sean_PennSource: http://www.imdb.com

While Mobster Squad wasn’t all that great of a movie, Sean Penn did a great job portraying the mob boss Mickey Cohen. Although, Penn playing a dark, angry, and violent mobster isn’t too much of a stretch.


Robert De Niro as Sam "Ace" Rothstein

Robert_De_NiroSource: http://www.imdb.com

Put Robert De Niro and Martin Scorcese together, and you know you’re going to get something special. In Casino, De Niro played Sam “Ace” Rothstein, a character based on the gangster Frank “Lefty” Rosenthal. His performance is exactly what you’d expect, a tough guy boss, living large and ruling with an iron fist.


Tom Hardy as Forrest Bondurant

Tom hardySource: http://entertainment.time.com

Tom Hardy’s another one of those versatile actors who can pull off pretty much any character he plays. In this case, in the movie Flawless, he plays Forrest Bondurant, a moonshine bootlegger in Prohibition Era America. Hardy easily fit into the skin of a larger than life personality who quickly became a local legend.


Ray Liotta as Henry Hill

ray liottaSource: http://theweek.com

In the movie Goodfellas, Ray Liotta played real-life mobster Henry Hill. Surprisingly, during production, Martin Scorcese didn’t want Liotta to meet Hill. However, after the movie, the two finally met, and the first thing Hill said to Liotta was, “Thanks for not making me look like a scumbag.”


Al Pacino as Benjamin "Lefty" Ruggiero

Al_PacinoSource: http://americanmafiahistory.com

Of course, Al Pacino will always be known as Michael Corleone. However, his role in Donnie Brasco as the real mafia mob boss Benjamin “Lefty” Ruggiero is an under-rated masterpiece performance. Fuggedaboutit.


Tom Hardy as the Kray Twins

tom hardy legendSource: http://ew.com/

What’d we say about Tom Hardy being able to play anyone? Well, in the movie Legend, he literally plays two people at the same time. Not many in the United States know much about the Kray twins, but in England, they’re mafia legends. Hardy definitely showed his acting chops by playing the two very distinct characters, one being particularly crazy and violent.


Johnny Depp as Whitey Bulger

depp whiteySource: http://variety.com

Depp returns as an infamous mob boss, but this time as the more recent Whitey Bulger. The terrifying performance set Black Mass apart and made people wonder if Depp would return to more serious roles. While Depp didn’t get any Academy nods for the role, he went all in and showed a man become increasingly brutal over time.


Jack Nicholson as Frank Costello

jack nickSource: https://www.youtube.com

The Departed is arguably one of the best mob movies in the last decade, and like a fine wine, it just keeps getting better with age. Jack Nicholson’s portrayal of Frank Costello anchors the movie and all the other characters. Some of the best performances are the father/son relationship between Nicholson and Leonardo DiCaprio, which slowly degrades into paranoia about a rat stirring up trouble.


Daniel Day-Lewis as Bill the Butcher

daniel day lewisSource: http://www.independent.co.uk

Daniel Day-Lewis is one of the greatest actors of our time if not of all time. His method acting causes him to absorb every aspect of his character, and it showed in the role of Bill the Butcher in Martin Scorcese’s Gangs of New York. While he didn’t win the Oscar for Best Actor that year, he certainly deserved it for another psychologically nuanced performance.


Robert De Niro as Al Capone

al caponeSource: https://www.youtube.com

Out of all the mob bosses in American history, Al Capone continues to be the most notorious. Who better to play him than Robert De Niro? In the movie Untouchables, De Niro got that chance and nailed it as the strong, charismatic leader hunted by the FBI.


Enjoy this post? Be sure to check out 25 Mobsters In Entertainment We Really Like But Shouldn’t.

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