Matt Damon Reveals the One Role That Got Away

Matt Damon, well-known for his work in films like The Martian and Oppenheimer, has spoken candidly about a project he regrets missing out on. Despite being replaced by someone he describes as “amazing”, Damon admits he was genuinely keen on the script and had already started digging into the real-life story behind it.

In a recent chat, Damon discussed his latest film, The Rip, where he teams up with Ben Affleck. The thriller sees Damon as a lawman who stumbles across a stash of cash, forcing him and his partner to question each other’s loyalty. The conversation soon turned to the pair’s long-standing careers and the legacy they’ve built over nearly thirty years in the business.

Missed Opportunity: The 'Milk' Biopic

When asked if there was a film he wishes he’d been part of, Damon pointed to the 2008 biographical drama, Milk. He explained,

“I was supposed to do Milk with Gus [Van Sant]. Then Sean [Penn] had something happen to his schedule and he had to push the movie, which made it a conflict for me, so I got recast with Josh Brolin.

“I loved the script, and I'd already done research on it. But as much as I wanted to be in that, it was probably better served by Josh. He was amazing. It was a moment in my 30s when I was like, 'That must've happened for a reason.' So I was sanguine about it at the end.”

Josh Brolin ultimately took on the role, earning himself an Academy Award nomination for Best Supporting Actor. The film, directed by Gus Van Sant and centred on a legendary activist, also picked up nods for Best Picture and Best Director, and won Oscars for Best Actor (Sean Penn) and Best Original Screenplay (Dustin Lance Black).

Back Together: Damon and Affleck’s Latest Collaboration

Damon and Affleck’s partnership is best remembered for the film that landed them an Oscar for Best Original Screenplay back in 1997. Since then, the pair have joined forces on several projects, with their latest effort, The Rip, backed by Netflix.

When asked about each other’s work, both actors had nothing but praise. Affleck said,

“Matt in Stillwater is incredible. The Informant! isn't always talked about, and The Good Shepherd is a really exquisite movie. It's a very subtle, very quiet but really piercing examination of the intelligence service in American history. I find it really beautiful. I'm a fan.”

Damon, in turn, shared his thoughts on Affleck’s performances:

“Ben's got a bunch of them, but the movie he put out right as COVID hit, The Way Back – that was a great performance… I've always been his biggest fan because we were each other's biggest fans when we didn't have any other fans in the world.

“But I do think this happens in middle age, as we get more life under our belts, that there's just been another level up for him this last decade. Like The Last Duel, which we wrote and nobody saw, but he's incredible in that movie. The Tender Bar, going all the way up through Air – he's just on a tear right now.”