Top 20 Greatest Movie Versions of Real-Life Gangsters
#20: Tom Hardy as the Kray Twins
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“Legend” (2015) Let’s be real here - Tom Hardy is great in everything. But he exudes that wonderful mixture of quiet ferocity and professional respectability that makes his dual performance of the Kray twins so fascinating. See also “Lawless,” where Hardy portrays prohibition-era gangster Forrest Bondurant. The Kray twins were brothers Ronnie and Reggie, and they were regarded as celebrities in the ‘50 and ‘60s. They ran the East End of London, mingled with prominent celebrities of the time, and were involved in the likes of murder, arson, and protection rackets. Critics didn’t adore the movie, but most agreed that Hardy was spectacular in the dual role, leading to numerous award nominations and wins.
#19: Johnny Depp as James "Whitey" Bulger Jr.
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“Black Mass” (2015) Johnny Depp’s performance as Whitey Bulger was seen as a massive comeback for the charismatic star, following a string of critical and financial disappointments like “Mortdecai” and “The Lone Ranger.” “Black Mass” follows the story of Boston crime boss, and FBI informant, Whitey Bulger. By 1999, Bulger was considered the second most-wanted person on the FBI’s Ten Most Wanted list, directly behind Osama bin Laden. Critics called it one of Depp’s finest performances, with many considering him legitimately frightening and intimidating. His was perhaps the biggest Oscars snub of the year.
#18: Sean Penn as Mickey Cohen
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“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 Mafia member and king of the Sunset Strip.
#17: James Cagney as Martin Snyder
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“Love Me or Leave Me” (1955) Cagney is one of the greatest movie stars of all time, and his turn as Moe the Gimp is nothing short of extraordinary. Moe the Gimp’s real name was Martin Snyder, a Chicago gangster active in the ‘20s and ‘30s. The film follows his relationship with singer Ruth Etting, who became known as “America’s Sweetheart of Song” for her dozens of hit records. Snyder managed Etting’s career, often pulling personal and political favors from his associates. Cagney perfectly conveys the volatile depth and unhinged violence of Snyder, and he earned himself an Academy Award nomination for his efforts. It was his third, and last, nomination.
#16: Vincent Cassel as Jacques Mesrine
“Mesrine” (2008) This French film has often garnered comparisons to Brian De Palma’s “Scarface,” although this one is actually based on a true, albeit extraordinary, story. French criminal Jacques Mesrine was a horrible man, responsible for numerous murders, kidnappings, and bank robberies. Throughout his career, Mesrine earned the moniker The Man of a Hundred Faces, as he had an incredible penchant for disguising himself and evading capture. He also escaped from prison on numerous occasions and once attempted to kidnap his sentencing judge. Vincent Cassel’s performance as Mesrine was universally lauded, with The New York Times calling him a combination of Robert Mitchum and Robert De Niro. It doesn’t get much better than that.
#15: Mark Wahlberg as Daniel Lugo
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“Pain & Gain” (2013) Despite the somewhat goofy title that makes it sound like a wrestling movie, “Pain & Gain” is a decent action comedy that proves one of Michael Bay’s more respectable efforts. Bay knows how to work with his actors, generating fantastic comedic chemistry and some strong performances, particularly from Mark Wahlberg in the role of Daniel Lugo. Lugo was the manager of Miami’s Sun Gym, and de facto leader of the Sun Gym Gang, a group of bodybuilders who were responsible for two murders and a kidnapping in the 1990s. Despite numerous historical inaccuracies and some questionable depictions of the criminals, Wahlberg’s performance is typically excellent and charismatic. And more than a little scary.
#14: Johnny Depp as John Dillinger
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“Public Enemies” (2009) Before he was Whitey Bulger, Johnny Depp proved that he could play criminals, with exceptional aplomb, in his role as John Dillinger. Dillinger is one of the most famous gangsters in American history, known for twice escaping from jail and robbing two dozen banks throughout the country. He was enormously popular at the time thanks to exaggerated media accounts, and he was famously gunned down outside Chicago’s Biograph Theater on July 22, 1934. His story was told in Michael Mann’s “Public Enemies,” and Depp’s performance as Dillinger garnered rave reviews. It’s Depp at his most natural and human, not bogged down by heavy makeup or goofy accents. There’s clearly something about him that makes for a compelling gangster!
#13: Delroy Lindo as West Indian Archie
“Malcolm X” (1992) In 1992, Spike Lee released the incredible “Malcolm X,” based on the autobiography of the legendary figure. Denzel Washington appears in the titular role, while Delroy Lindo plays gangster “West Indian” Archie. Archie co-operates an illegal numbers racket with Malcolm and eventually confronts him over some gambling winnings. The story of Archie comes primarily from the eighth chapter of Malcolm X’s autobiography, where it’s claimed that a tense confrontation with Archie was one of the reasons for Malcolm fleeing Harlem. Such a dangerous and threatening person requires a great actor, and Delroy Lindo portrays Archie with just the right amount of eerie discomfort.
#12: Cliff Curtis as Pablo Escobar
“Blow” (2001) It doesn’t get much worse than Pablo Escobar. Escobar is perhaps the most famous drug runner in history, known for creating and leading the Medellín Cartel. His Cartel dominated the American cocaine trade, leaving Escobar with an estimated net worth of some $30 billion. The Cartel was also incredibly dangerous and killed upwards of 3,500 people, including hundreds of innocent civilians in plane and truck bombings. In Ted Demme’s (demmy) “Blow,” Escobar is portrayed by Cliff Curtis. “Blow” follows the story of George Jung (played once again by Johnny Depp!), an American cocaine smuggler who worked for Escobar and the Cartel. Curtis does a stellar job portraying the outwardly friendly, yet viciously violent Escobar.
#11: Tim Roth as Dutch Schultz
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“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, who is portrayed with sardonic verve by Andy Garcia, 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.
#10: Joe Pesci as Russell Bufalino
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“The Irishman” (2019) Much was made of “The Irishman” owing to its awesome cast, which includes the likes of Robert De Niro, Al Pacino, and Joe Pesci in an exceedingly rare role. Pesci played Russell Bufalino, the acting boss of the Bufalino Family of Northeastern Pennsylvania. If “The Irishman” is to be believed, this crime family was responsible for the murder and famous disposal of union leader Jimmy Hoffa. Both “The Irishman” and Pesci’s performance earned widespread acclaim, leading to his third Academy Award nomination, and first since 1990. The nomination was fully deserved, as Pesci is utterly magnetic throughout the long movie, particularly at the end when the elderly Bufalino and Frank Sheeran are reminiscing on their time together.
#9: Robert De Niro as Al Capone
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“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: Jack Nicholson as Jimmy Hoffa
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“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.
#7: Al Pacino as Benjamin “Lefty” Ruggiero
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“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.
#6: Warren Beatty and Faye Dunaway as Clyde Barrow & Bonnie Parker
“Bonnie and Clyde” (1967) This landmark film broke numerous Hollywood taboos of the time, including depictions of sexuality and graphic violence. Both are highly necessary for this tale. Bonnie and Clyde became two of the most famous gangsters in American history via the Barrow Gang in the 1930s. This gang is known for their countless robberies, murders of both police officers and civilians, and for the resulting media sensationalism - particularly in regards to the depiction of Bonnie Parker. Their story was re-energized in 1967 with the release of the film starring Warren Beatty and Faye Dunaway in the titular roles. Despite some controversial glamorization, their performances earned widespread acclaim, and both received Academy Award nominations.
#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 Warren Beatty when he depicts mobster-turned-hotelier-turned Vegas big shot, Bugsy Siegel. Beatty plays Bugsy as a man with a 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
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“Gangs of New York” (2002) Day-Lewis is one of those actors that completely transforms themselves 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
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“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
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“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.
#1: Ray Liotta as Henry Hill
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“Goodfellas” (1990) As great as Joe Pesci is as Tommy DeVito, we have to give this one to Ray Liotta as Henry Hill. 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…
