Fun
Frisky
Nostalgic
Intense
Adventurous
Choked Up
Curious
Romantic
Weird
Johnny Depp, occasional pirate and wearer of scarves, is reportedly back in the Oscar game with Black Mass, Scott Cooper’s bloody new biopic depicting the life of South Boston gangster James “Whitey” Bulger. Depp, who embodies Bulger with slick grey hair, icy blue eyes, and a rapt, relentless trigger finger, has created quite the buzz with his performance, which is currently coming down off a Toronto International Film Festival high and seamlessly shifting into wide release gear. Though Cooper’s ambitions have received mixed reviews, it’s Depp who allegedly transcends the film, now playing in a theater near you.
But wait a minute, you say? Martin Scorsese already made a movie about Whitey Bulger, right? And won Best Picture for it? Well yes, The Departed and Jack Nicholson’s character Frank Costello were loosely based on Bulger’s story, but that film was actually a remake of Japan’s Infernal Affairs, an equally bloody gangster noir that revolves around a similar saga of police infiltration of organized crime. Nicholson’s rendition of a variation of Bulger, however, still serves its purpose in a subgenre of crime fiction based on real-life notorious, violent figureheads.
So how do other portrayers of history’s most hardened criminals stack up against one another? Some are downright terrifying while others offer quietly brooding, but equally sinister performances. See if you agree with our ranking below of who embodied who best.
Brad Pitt as Jesse James, 'The Assassination of Jesse James by the Coward Robert Ford'
Having one of Hollywood’s most handsome men star as Jesse James perhaps gives the famed leader of the Missourian gang of bandits a little too much credit. James wasn’t necessarily a looker in the conventional sense of the word, but he was a tactical, charismatic outlaw whose charm won over the hearts of Southerners far and wide — but pissed off enough of his own men to get him shot in the back. [Where to stream The Assassination of Jesse James by the Coward Robert Ford]
Robert De Niro as Al Capone, 'The Untouchables'
If you’re going to have anyone play Al Capone in a Brian De Palma movie, you may as well cast the best fake gangster in the business. De Niro owned it as the infamous bootlegger, but it’s worth arguing that if James Gandolfini had been as big a star as he was circa 2001 back in 1987, he — with his hairline and husky stature — would have made for the perfect Capone. [Where to stream The Untouchables]
Fernando Rey as Alain Charnier, 'The French Connection'
Rey starred as French heroin trafficker Alain Charnier in William Friedkin’s drama about a car chase with some detective work sprinkled throughout. Despite being of Spanish descent, Rey gave a timeless performance as the deadly Frenchman Charnier, who, at times, you couldn’t help but root for. [Where to stream The French Connection]
Faye Dunaway as Bonnie Parker, 'Bonnie and Clyde'
Bonnie Parker was, by no means, a blonde bombshell like Dunaway. She was, however, a fierce broad who knew how to sling a pistol in addition to unofficially introducing “the skinny arm.” Dunaway’s badassery in Arthur Penn’s classic crime film arguably did the legacy of Bonnie Parker justice, depicting her as an all-American everywoman who, for every dollar she stole with her partner Clyde Barrow, let innocent, tax-paying citizens keep their share. [Where to stream Bonnie and Clyde]
Denzel Washington as Frank Lucas, 'American Gangster'
Though the real Frank Lucas has publicly stated that only a small portion of the events that occurred in Ridley Scott’s biopic were true, the former heroin smuggler was overwhelmed by the accuracy of Denzel Washington’s portrayal. [Where to stream American Gangster]
Al Pacino as Benjamin "Lefty" Ruggiero, 'Donnie Brasco'
Pacino has a way, in many of his roles as an organized crime leader, of being equally chilling and endearing — ultimately proving to us how undercover FBI agent Joseph Pistone (Johnny Depp) became so enthralled with his target in the first place. [Where to stream Donnie Brasco]
Tom Hardy as Charles Bronson, 'Bronson'
From Ronald and Reggie Kray in the upcoming Legend to Peaky Blinders‘ bootlegger Alfie Solomons, there’s no denying that Tom Hardy is terrifyingly great at portraying real-life criminals. But before you see double the Hardy as the Kray twins in the upcoming biopic, check out the actor’s knockout performance as bare-knuckle boxer Charles Bronson in Nicholas Winding Refn’s harrowing prison drama. [Where to stream Bronson]
Jack Nicholson as Frank Costello, 'The Departed'
We previously mentioned how Nicholson’s ruthless, manic Frank Costello is a loosely reimagined version of Whitey Bulger. While Scorsese’s rendition isn’t as true to the history books as Black Mass is said to be, Nicholson gives a commanding, nightmare-inducing performance as one of Boston’s most-feared criminals. [Where to stream The Departed]
Al Pacino as Sonny Wortzik, 'Dog Day Afternoon'
Still riding The Godfather wave, starring as Michael Corleone only helped Pacino cement the legitimacy of embodying real-life criminal John Wojtowicz (named Sonny Wortzik for the film’s purposes). Whether or not this is the work of perfect casting or Pacino’s frequent work making him the ultimate anti-hero throughout the ’70s, there’s no denying how closely the actor and bank robber resemble one another. [Where to stream Dog Day Afternoon]
Robert De Niro as James Conway, 'Goodfellas'
De Niro strived to become Jimmy “The Gent”Burke so much so (Conway was Burke’s birth name), the actor was rumored to have met with the real Henry Hill to ask him questions about Burke’s interests (besides, you know, the obvious), mannerisms, and specifically, how he would typically hold his cigarettes. [Where to stream Goodfellas]
Like what you see? Follow Decider on Facebook and Twitter to join the conversation, and sign up for our email newsletters to be the first to know about streaming movies and TV news!
