Matt Damon Opens Up About Losing 'Milk' Role to Josh Brolin

Matt Damon, celebrated for his performances in films like The Martian and Oppenheimer, recently revealed the one film that slipped through his fingers. While he praised his replacement’s performance, Damon admitted he was deeply invested in the project, having already researched the real-life story behind it.

During a recent interview, Damon discussed his latest action thriller, The Rip, where he stars alongside Ben Affleck. The film follows two law enforcement partners who stumble upon a large sum of money, forcing them to question each other's loyalty. As Damon and Affleck looked back on their nearly thirty-year careers, the conversation turned to the projects that left a lasting impression.

Missing Out on 'Milk'

When asked about a film he wishes he could have made, 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 an Academy Award nomination for Best Supporting Actor. The film, directed by Gus Van Sant and centered on the life of a groundbreaking activist, also received nominations for Best Picture and Best Director. It went on to win Best Actor for Sean Penn and Best Original Screenplay for Dustin Lance Black.

Reuniting With Ben Affleck for Netflix 's 'The Rip'

Damon and Affleck’s partnership has been a defining force in their careers. Their most notable collaboration, Good Will Hunting, earned them an Oscar for Best Original Screenplay in 1997. Since then, the duo has teamed up on several projects, with Netflix supporting their latest venture.

When reflecting on each other's work, both actors expressed genuine admiration. Affleck highlighted some of Damon's standout roles, saying,

"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 appreciation for 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."