Josh Brolin Landed Matt Damon's Dream Role After Scheduling Chaos
A Hollywood casting shuffle led to one actor's disappointment and another's Oscar nomination. The behind-the-scenes story reveals how timing changed everything for a major biopic.
Matt Damon recently opened up about losing what he calls his biggest career regret. The actor was originally set to star in Gus Van Sant's acclaimed 2008 biopic but got bumped due to a scheduling nightmare that reshuffled the entire production.
During a recent conversation with USA Today about his upcoming action thriller The Rip, Damon revealed the painful details. He was supposed to work with director Van Sant on the Harvey Milk story. Then Sean Penn's schedule shifted, forcing the entire movie to be pushed back.
"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," Damon explained.
The Role That Got Away
Damon had already invested serious time preparing for the part. He'd studied the script extensively and conducted research on the real-life story of the groundbreaking activist and politician. The project meant something personal to him.
"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," he said.
Josh Brolin stepped into the role and delivered a performance that earned him an Academy Award nomination for Best Supporting Actor. The film itself became a critical darling, collecting nominations for Best Picture and Best Director. Sean Penn won the Oscar for Best Actor, and Dustin Lance Black took home the award for Best Original Screenplay.
Reuniting With Ben Affleck
The interview came as Damon promotes The Rip, his latest collaboration with longtime friend and creative partner Ben Affleck. Netflix is backing their new action thriller, which follows a law enforcement agent who discovers a large sum of money and must navigate questions of loyalty with his partner.
The duo's partnership dates back to their breakthrough success with Good Will Hunting in 1997, which earned them both an Oscar for Best Original Screenplay. They've continued working together across multiple projects over nearly three decades in Hollywood.
When discussing each other's work, both actors showed mutual admiration. Affleck praised several of Damon's performances, singling out Stillwater, The Informant!, and The Good Shepherd as standout work that doesn't always get the recognition it deserves.
Damon returned the compliment, highlighting Affleck's recent hot streak: "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 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."