Depp reportedly watched FBI surveillance footage of Bulger and spoke to his former attorney to nail the man’s mannerisms. (The film itself received middling reviews from critics, but Depp’s performance was praised.) Black Mass can be viewed on Amazon, YouTube, or iTunes.

The Departed

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

The Departed was originally an adaptation of the 2002 Hong Kong thriller Infernal Affairs, but Scorsese said Nicholson wanted an extra element to make the story more immediate. That’s when screenwriter William Monahan came up with the idea to base Nicholson’s and Damon’s characters on Bulger and Connolly, respectively. Leonardo DiCaprio plays a young state trooper who goes undercover in Costello’s organization as he races to discover Costello’s mole before Costello realizes he’s a cop.

When the film was released, Bulger was still on the run. He was reportedly seen watching The Departed in a movie theater in San Diego that year, a tipster told the Boston Globe. The Departed can be viewed on Amazon, YouTube, or iTunes.

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

Three years after Bulger was captured in 2011, and a few months following his sentencing of two consecutive life terms in prison, CNN Films co-produced this documentary about the mobster’s life and various trials. It premiered at the 2014 Sundance Film Festival and received solid reviews from critics, though they noted that Bulger’s life of crime was perhaps too sprawling for any one documentary to cover completely.

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

Other roles inspired by Bulger

A number of major television characters are based in part on Bulger. These include:

The film that never was

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

“We had a very different take on it,” Damon told the Hollywood Reporter in 2015. He said that he and Affleck had received a letter from a South Boston author that made them rethink the project. “It was a really moving letter that basically said: ‘Don’t glorify this man any more. Please stop.’ And this is to take nothing away from Black Mass. I hear the movie’s great. But Ben and I agreed with the guy who’d written us. And so we came up with this idea of doing it more like an anti-gangster movie. Make it look like what it was: something grotesque.”

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