The life of James “Whitey” Bulger has always been the stuff of great crime fiction. Born in Boston in 1929, Bulger worked his way up the criminal ladder from street-level tough guy to citywide mob boss (and occasional FBI informant) before going on the lam in the early ’90s. A global manhunt followed, ending with his eventual discovery and arrest in 2011, after which he received a life sentence. Now, in another twist straight out of the movies, the 89-year-old was found dead at a federal prison in West Virginia. (At press time, the cause of death has yet to be disclosed.)
It’s a highly cinematic capper to a story that has already inspired a number of movies and TV shows that feature a Bulger-like character — and sometimes even Bulger himself. Here are some of the most notable works based on his life story and where you can watch them.
Black Mass (2015; available for rent or purchase on Amazon, iTunes, and YouTube)
Johnny Depp transformed himself into Boston’s crime kingpin for Scott Cooper’s star-powered drama, which unfolds between the ’70s and ’90s, when Bulger was recruited to be an FBI information by John Connolly (played by Joel Edgerton). Depp was nominated for a SAG Award for his performance, but the real Bulger supposedly gave him a thumbs-down. “Johnny Depp might as well have been playing the Mad Hatter all over again as far as James Bulger is concerned,” Bulger’s attorney, Hank Brennan, told People in 2015.
The Blacklist (2013-present; airs on NBC, past seasons are available to stream on Netflix)
NBC’s hit procedural imagines would what happen if a Bulgeresque criminal mastermind — in this case, James Spader’s Raymond “Red” Reddington — decided to use the rest of his remaining years in lock-up feeding intel to federal authorities … including his long-lost daughter.
Ray Donovan (2013-present; airs on Showtime, past seasons are available to stream on Showtime Anytime)
Season 1 of Liev Schreiber’s popular Showtime serial features James Woods as Boston bad guy Patrick “Sully” Sullivan, who shows up in L.A. and gets involved in Donovan father-son drama. Here’s one nice thing you can say about the otherwise not-nice Sully: He gives the Donovans a common enemy who brings the clan together.
The Town (2010; available for rent or purchase on Amazon, iTunes, and YouTube)
Hometown boy Ben Affleck directed and stars in this Beantown-based crime caper, populated by A-listers like Jeremy Renner, Blake Lively, and Jon Hamm. In one of his final screen performances before his 2011 death, British actor Pete Postlethwaite played Fergus “Frankie” Colm, the Boston gangster who employs Affleck’s reluctant crook.
The Departed (2006; available for rent or purchase on Amazon, iTunes, and YouTube)
While Martin Scorsese’s Oscar-winning gangland epic is adapted from a hit Hong Kong franchise, he and screenwriter William Monahan re-tailored the story to suit the Boston setting. That included modeling Jack Nicholson’s larger-than-life goodfella, Frank Costello, after Bulger. However, the real Bulger’s behavior was too extreme even for Scorsese. “We tried to utilize the information we read about it as a kind of comfort zone to know that a lot of the stuff was factual, because if somebody had written that, I’d say, ‘No, come on. It’s too much,'” the director remarked on a DVD bonus feature.
Brotherhood (2006-2008; available to stream on Amazon and Hulu)
While Whitey Bulger was rising through Boston’s criminal ranks, his brother, William, became a mainstay in Massachusetts politics, serving as the state senate majority leader for 18 years. The diverging paths of the Bulger brothers provided a jumping-off point for this two-season Showtime series, which follows the intertwined lives of the Rhode Island-based Caffee siblings, Michael (Jason Isaacs) and Tommy (Jason Clarke). The former is a career criminal looking to get back into the game, while the latter deals with the bruising world of state government.
Monument Ave. (1998; available on DVD)
Funnyman Denis Leary got serious in this Ted Demme-directed crime drama as a mentor to his criminal-in-training cousin (Jason Barry). Acclaimed Irish actor Colm Meaney plays their trigger-happy employer, Jackie O’Hara — a Bulger stand-in whose own corruption infects everyone in his inner circle.
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