Matt Damon talks about his Whitey Bulger biopic that never was

Last Updated on August 2, 2021

Whitey Bulger was once of those “ideas” that multiple studios wanted a piece of. A few years ago, there were a couple of Bulger biopics in development, with each one racing, in typical fashion, to be the first one out of the gate and ultimately command the attention at the box office. One of those films turned out to be BLACK MASS, which we saw a few weeks ago, starring Johnny Depp as the infamous Boston gangster. The other was set to star Matt Damon as Whitey Bulger, with Ben Affleck stepping behind the camera to direct and Ben’s brother Casey playing Whitey’s brother Billy. That film eventually stalled out, and with BLACK MASS getting rolling over at Warner Bros., it never really had much of a chance to get started up again.

Not much has been said about what Damon and Affleck were planning to do. However, while promoting THE MARTIAN, Damon did finally spill the beans a bit about the direction he and Affleck were looking to take with their approach to the material, which would have been far different than what BLACK MASS turned out to be.

Ben and I had an idea that we would do it more like ‘Unforgiven’ — which was the anti-western. We wanted to do the anti-gangster movie. I got a letter from somebody — from a writer in South Boston when [Bulger] got caught and we announced that we were going to do this story. He sent me this letter and he was like, ‘Don’t glorify this guy anymore. Just stop. Please. He caused so much damage to so many people.’
 

And so it didn’t sit well with me. And then as I thought more about it, and Ben and I talked about it, what we realized was there was a way to do a movie that really explored all of our complicity in the raising up of this guy. . . . And, look, I was in ‘The Departed,’ so I’m not knocking anybody. I’m just saying what our way in was going to be, and I think it’s very different than anything that’s been done before and I was really excited about it.

It’s definitely a take on Bulger that BLACK MASS didn’t seem willing to get into, and could certainly make for an interesting movie if it ever got made. But with Affleck a bit busy being Batman for the next few years and Damon always off doing his own thing (BOURNE included), we may just have to chalk this one up as another of those films that wound up getting away.