Matt Damon has publicly shared that he lost the role he most regrets in three decades of filmmaking: a part in Gus Van Sant’s 2008 biographical drama Milk.
In a joint interview with Ben Affleck for USA Today on Jan. 15, 2026, Damon pinpointed Milk as “the one that got away.”
The Scheduling Conflict That Changed the Cast
“I was supposed to do Milk with Gus,” Damon told the outlet. “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 had already completed research on the script and was enthusiastic about the project.
- The delay triggered by Penn’s calendar shift forced the actor to withdraw.
- Brolin ultimately portrayed politician Dan White, the man who assassinated Harvey Milk and San Francisco mayor George Moscone in November 1978.
Award-Winning Results
Milk went on to major awards success:
| Category | Outcome |
|---|---|
| Sean Penn | Won Academy Award for Best Actor |
| Josh Brolin | Nominated for Best Supporting Actor |
Damon praised the final result, saying, “It was probably better served by Josh. He was amazing.” The actor added that the experience taught him a broader lesson: “That must’ve happened for a reason. So I was sanguine about it at the end.”
Current Collaboration
Damon and Affleck used the interview to promote their latest joint project, the Netflix action thriller The Rip. In the film:
- Damon plays Lt. Dane Dumars
- Affleck plays Detective Sergeant J.D. Byrne
- Both characters are Miami officers whose loyalties are tested after finding a large sum of cash
Director Joe Carnahan based the script on a real incident involving a friend who headed tactical narcotics for the Miami-Dade police department. The Rip is now streaming on Netflix.
