Who Should Play Whitey Bulger in Black Mass?

Depp is definitely out. So who are the next best contenders to play the Boston crime boss?

Whitey Bulger

So Johnny Depp officially dropped out of the Whitey Bulger biopic Black Mass, based on the book written by Globe journalists Dick Lehr and Gerard O’Neill. Now that Depp is out, producers of the movie are probably scrambling to find a solid contender to play the role of Whitey Bulger. So what kind of gangster guy should producers be looking for?

“They are probably planning on starting when [Whitey] is young, I suppose. So it’s going to be really challenging to find someone because these [filmmakers] are going to need to go from his youth all through his current age at 83,” says author Alison McLennan, a Whitey Bulger expert who wrote her novel Falling for Johnny based on Bulger. “I was thinking Anthony Hopkins for the older man.”

McLennan also adds, “If they’re going to use one actor, it’s going to be a huge challenge. They’d definitely need somebody with an Irish or Scottish heritage. Whitey’s also famous for those icy-blue-on-grey eyes. And maybe somebody from Boston who can get the accent down.”

All valid characteristics necessary for Whitey. But let’s not forget that Black Mass has very modest budget of $60 million for the project. Depp was offered a measly $10 million for the role of Whitey—for which Depp shook his head and said, “Yeah, I don’t think so.” Jack Sparrow does not settle for $10 million. So not only does the Black Mass leading man need to be Irish-American, timeless-looking with a convincing Boston accent, but this guy also needs to be a cheap date. (Is $10 million really considered cheap nowadays?) So, sorry ladies, Anthony Hopkins and Ryan Gosling will have to save their icy-blues for something else.

And finally, some words of advice to these actors from Ben Affleck: “It’s one of those things: If you do Whitey, you better make damn sure you execute and make a good movie.”

Take a look at some of my contenders:

Desmond Harrington

Harrington is best known for his role on Showtime’s Dexter as the conniving baller, Detective Joey Quinn, and his previous role as Chuck’s skeevy uncle Jack Bass in Gossip Girl. He’s good at playing the manipulative law breaker. Harrington also grew up in the Bronx.

Anthony Michael Hall

We all know Anthony Michael Hall as the geeky youngster in John Hughes’s iconic ’80s film The Breakfast Club. But Hall grew up in West Roxbury (accent, check!) and had a significant role in The Dark Knight. So he’s definitely familiar with city crime dramas (yes, Gotham City counts).

Denis Leary

Leary grew up in Worcester, is the son of two natives of Ireland, and even attended Emerson College. Although Leary dabbles mostly in comedy, but his performance in The Amazing Spiderman as Captain Stacy is pretty solid as a crime-fighting hardass.


Damian Lewis

Although the majority of Lewis’s roles take on politics and war, I’m convinced he’d be a fabulous Whitey Bulger. His character of Nick Brody in Showtime’s Homeland is an outstanding example of Lewis portraying a conniving political figure whom every person falls for.