Regional crime boss James Joseph “Whitey” Bulger has a curiously strong hold on the imaginations of filmmakers. As one of the last of a largely bygone generation of gangsters, Bulger has become an inspiration for those looking to create screen villains — Jack Nicholson’s character in The Departed, for example, was based on Bulger. So was Pete Postlethwaite’s character in The Town.

The Boston-area criminal has captured the interest of Boston-area filmmakers Ben Affleck and Matt Damon as well, and the two have planned a Bulger film for a couple years now. Looks like the will be beat to the punch, however, by Barry Levinson. The director is attached to Black Mass, a film based on Dick Lehr and Gerald O’Neill’s 2001 book Black Mass: The True Story of an Unholy Alliance Between the FBI and the Irish Mob.

Now Levinson has landed Johnny Depp — star of the Levinson-produced crime film Donnie Brasco — to play Bulger. That gives Black Mass serious momentum. Read More »

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It was announced earlier this week that Ben Affleck and longtime pal Matt Damon would reunite for a biopic about Whitey Bulger, with Casey Affleck set to co-star. We now have a more information about the younger Affleck’s part. He’ll be playing Bill Bugler, little brother of Whitey Bugler (Damon’s role). Unlike notorious gangster Whitey, Billy was an upstanding member of society — Korean war vet, lawyer, politician, and educator. He lost his post as the president of the University of Massachusetts in 2003 when he was found to have spoken with his fugitive brother in secret.

In addition to starring, Damon will also script the film; Affleck the Elder will direct and co-star. It’s unclear when exactly the picture will get off the ground, as both brothers and Damon have plenty of other projects on their plates. But they’ll have to get moving if they want to beat the two other Whitey Bulger movies in the works — there’s one in development with producer Graham King, who produced The Departed, and another titled Black Mass, which was scripted by Russell Gerwitz. [Showbiz 411 via The Playlist]

After the jump, new jobs for Dylan McDermott, Rufus Sewell, Gabriel Byrne, and Toby Stephens.

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Matt Damon and Ben Affleck earned worldwide fame and screenwriting Oscars thanks to the film Good Will Hunting. While each has developed his own career in the years since, the possibility of another collaboration between Affleck and Damon has always been a subject of inquiry. Now, only days after Damon announced his intent to direct his first film (an as-yet untitled legal drama he co-wrote with John Krasinski) and Affleck was said to be the chosen director for The Stand, we’ve got word that the two are going to re-team for a new Boston-set picture.

The subject of the film, which Affleck will direct, is recently captured gangster James ‘Whitey’ Bulger. Whitey Bulger was a prominent member of Boston’s notorious Winter Hill Gang (named for a Somerville, MA neighborhood) starting in the early ’70s, and took control of the gang in ’79. He  fled Boston in the mid-’90s and was on the run until this past summer, when he was arrested in Santa Monica. Other producers are putting together their own Whitey Bulger films, so will Affleck and Damon be able to beat them to the screen? Read More »

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