(Credits: Far Out / YouTube Still)
Sat 14 March 2026 18:45, UK
Part and parcel of being an actor is missing out on roles that you’re desperate to play, although Matt Damon has navigated the last three decades without having to worry about it too much.
Ever since Good Will Hunting transformed him from a relative unknown to an Academy Award winner overnight, he’s been hovering around the top of the casting wish list. He’s served his time as a slumming, jobbing upstart who couldn’t get a job to save his life, which hasn’t ruled him out of having any regrets.
Edward Norton’s turn in Primal Fear was the first one that got away, because Damon was fully aware that it would be a career-maker for the person who was eventually cast, which it was, even if there’s a bizarre alternate timeline out there where Danny Dyer’s audition was successful and he played Aaron Stampler.
Once he’d solidified himself as a star, though, he was the one being offered the parts instead of having to scrap for them. James Cameron’s recollection of the Avatar scenario is different from his, but apart from the eye-watering volume of money he missed out on, Damon won’t look back at not playing Jake Sully and rue the day.
That’s not the case with Dan White, who definitely fit the bill. No stranger to working with Gus Van Sant, the Good Will Hunting and Gerry collaborators were signed, sealed, and delivered to reunite on the filmmaker’s biographical drama, Milk, and the ink on the contract had well and truly dried by early 2007.
Unfortunately, Damon hit a roadblock. Van Sant wouldn’t make the film without Sean Penn in the title role, with scheduling conflicts rearing their ugly head. The start of production was pushed back to January 2008, and he’d already committed to re-teaming with another frequent creative partner, Steven Soderbergh, for The Informant!
When USA Today asked him about the one that got away, he only had one regretful answer. “I was supposed to do Milk with Gus,” he explained. “Then Sean 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,” Damon added, but not without praising his replacement. “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 have happened for a reason’. So I was sanguine about it at the end.”
Sanguine or not, Brolin notched an Oscar nomination for ‘Best Supporting Actor’, which may well have happened to Damon had those scheduling issues not arisen. It took Milk almost 20 years to reach the screen, but it was a matter of months that ruled him out of the role.
