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James “Whitey” Bulger is dead, but the notorious crime boss will live ~ above in the renowned imagination and on the screen.

Bulger, 89, was discovered dead in a West Virginia prison today, according to various reports. He was serving 2 life sentences for 11 murders, and also had just been moved from a facility in Florida to the high-security prison in West Virginia this past week. The new York time reports the he was beaten to fatality by two mob-affiliated inmates, citing 2 unnamed jail officials.

It’s an ignominious end for the Irish-American gangster, whose wild, stranger-than-fiction life before and also after that went ~ above the lam in 1994 and also became one of America’s many wanted criminals has actually been written about extensively (including in a biography by two Boston world reporters), and also depicted on screen several times. While countless American “mob boss” personalities today are based loosely on Bulger—or room composites of renowned American mobsters, consisting of Bulger—two major Hollywood productions and a documentary attribute Bulger prominently:

Black Mass

The many recent—and direct—adaptation of Bulger’s story is Black Mass, the 2015 biopic starring Johnny Depp in a duty that earn the gibbs a display screen Actors Guild award nomination. Reviewers said the role was one of the finest in numerous years for Depp, who donned a fake receding hairline, poor teeth, and also bright blue contacts to end up being the infamous mobster.


The film picks increase in 1975, once Bulger was already the head of the powerful Winter Hill gang crime company in and also around Boston. Joel Edgerton plays john Connolly, an FBI agent who grew up with Bulger and also eventually came to be his handler as an informant. Connolly was successfully handled rather by Bulger, coming to be his eyes and ears inside the bureau and helping the crowd boss undermine rival gangs, and also covering up killing he was associated in or ordered. The real-life Connolly is currently serving the end the remainder that a 40-year sentence authorize in 2008, ~ he to be convicted of 2nd degree murder.


Depp apparently watched FBI surveillance footage of Bulger and spoke come his former attorney to nail the man’s mannerisms. (The movie itself got middling evaluate from critics, however Depp’s performance was praised.) Black Mass have the right to be perceived on Amazon, YouTube, or iTunes.

The Departed

Martin Scorsese’s 2006 crime film, which winner the Oscar for best photo the following year, was loosely based on Bulger and also his Winter Hill Gang. The movie legend Jack Nicholson plays candid Costello, the leader of a crime syndicate in Boston, while Matt Damon theatre Colin Sullivan—Costello’s mole within the Massachusetts State Police, who’s clearly inspired by Connolly and also his relationship to Bulger.


The Departed was originally an adaptation of the 2002 Hong Kong thriller Infernal Affairs, but Scorsese said Nicholson want an extra facet to make the story much more immediate. That’s when screenwriter wilhelm Monahan came up through the idea to basic Nicholson’s and Damon’s personalities on Bulger and also Connolly, respectively. Leonardo DiCaprio dram a young state trooper who goes undercover in Costello’s company as he races to uncover Costello’s mole before Costello realizes he’s a cop.


When the film was released, Bulger was still top top the run. The was supposedly seen watching The Departed in a movie theater in mountain Diego the year, a tipster called the Boston Globe. The Departed deserve to be regarded on Amazon, YouTube, or iTunes.

Whitey: United claims of America v. James J. Bulger

Three year after Bulger was captured in 2011, and a couple of months following his sentencing of two consecutive life state in prison, CNN movies co-produced this documentary around the mobster’s life and also various trials. It premiered at the 2014 Sundance movie Festival and received solid evaluate from critics, despite they noted that Bulger’s life the crime was maybe too sprawling for any type of one documentary to cover completely.

Whitey: United claims of America v. James J. Bulger can be perceived on Hulu and Amazon.

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Other roles inspired by Bulger

A number of significant television personalities are based in part on Bulger. This include:

“Sully Sullivan” in the Showtime crime drama Ray Donovan (played by James Woods)“Paddy Doyle” in TNT series Rizzoli & Isles (played by john Doman)“Raymond ‘Red’ Reddington” in NBC crime series The Blacklist (played by James Spader)

The movie that never was

Fellow Bostonians Matt Damon and Ben Affleck were reportedly working top top a film with Warner Bros, scripted by Terence Winter (the creator and also writer of Boardwalk Empire), yet it did not move forward after Black Mass was released in 2015.

“We had a very different take it on it,” Damon called the Hollywood Reporter in 2015. He said that he and also Affleck had received a letter from a southern Boston writer that made them rethink the project. “It to be a really relocating letter that basically said: ‘Don’t glorify this man any kind of more. You re welcome stop.’ and this is to take nothing far from Black Mass. I hear the movie’s great. But Ben and also I agreed through the guy who’d created us. And so we come up with this idea of act it much more like an anti-gangster movie. Do it look choose what the was: something grotesque.”