Matt Damon Reveals the Film Role That Slipped Away
Matt Damon opens up about a major part he nearly played, why he had to step aside, and how the experience shaped his outlook—while reflecting on his creative partnership with Ben Affleck.
Matt Damon, a familiar face to British cinemagoers thanks to his turns in The Martian and Oppenheimer, has spoken candidly about a role that narrowly eluded him. While he’s quick to praise the actor who eventually took the part, Damon admits he was rather taken with the script and had already begun delving into the real-life story behind it.
In a recent chat, Damon discussed his latest venture, The Rip, an action thriller where he stars alongside Ben Affleck. The pair, who have spent nearly thirty years navigating the film industry together, found themselves reminiscing about their careers and the projects that have defined them.
Missed Opportunities and Unexpected Turns
When pressed on which project he most regrets missing, Damon didn’t hesitate to name 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.
He went on,
“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 stepped into the role, earning himself an Academy Award nomination for Best Supporting Actor. The film, directed by Gus Van Sant and centred on a renowned activist, also picked up nods for Best Picture and Best Director, and took home Oscars for Best Actor (Sean Penn) and Best Original Screenplay (Dustin Lance Black).
Creative Partnerships and Mutual Admiration
Damon’s collaboration with Affleck is the stuff of Hollywood legend, their most celebrated effort being Good Will Hunting, which saw them both collect Oscars for Best Original Screenplay back in 1997. Since then, the duo have joined forces on several occasions, with their latest project, The Rip, backed by Netflix.
Asked to reflect on each other’s work, Affleck didn’t hold back in his praise for Damon, singling out a few personal favourites:
“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, highlighted Affleck’s recent 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.”