Matt Damon Lost A Role That Turned Josh Brolin Into An Oscar Nominee
We may receive a commission on purchases made from links.
Matt Damon has had one hell of a career. Damon has starred in many, many great movies during the course of his decades-long run in Hollywood. From his third act turn in "Saving Private Ryan" to his pivotal role in Martin Scorsese's "The Departed," his resume is impressive, to say the least. But that doesn't mean it's all worked out perfectly. For Damon, there's at least one movie he missed out on, and it led to Josh Brolin ("No Country for Old Men") landing an Oscar nomination.
In an interview with USA Today tied to his role in director Joe Carnahan's "The Rip" (a crime thriller loosely based on real-life events), Damon was asked if there was one movie that "got away" during the course of his career. He name-checked 2008's Oscar-winning "Milk," which would have re-teamed him with director Gus Van Sant. Here's what Damon had to say about it:
"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."
Damon and Van Sant previously collaborated on "Good Will Hunting" (which was very nearly an action movie, believe it or not), a film that proved to be a breakout moment for the actor and his frequent creative partner Ben Affleck (who co-starred in and wrote the movie with Damon).
Josh Brolin and Matt Damon worked together after Milk
Based on the real life story of legendary queer rights activist and politician Harvey Milk, "Milk" follows its namesake (Sean Penn) as he leaves New York for San Francisco with his lover Scott Smith (James Franco) in the 1970s. Determined to accomplish something meaningful with his life, Milk proceeds to open a camera shop in the Castro District, helping to transform the area into a haven for LGBTQ+ people. He eventually goes on to win a seat on the Board of Supervisors and becomes the first openly gay man elected to a notable public office in California, only for tragedy to strike when his fellow politician, Dan White (Josh Brolin), kills Milk in cold blood a year later.
"Milk" was a somewhat modest commercial success but a critical triumph and was nominated for eight Academy Awards, including Best Picture. Penn would go on to win the Best Actor Oscar for his turn in the film, while Brolin received a Best Supporting Actor nomination. Of course, the latter lost to Heath Ledger, who posthumously won an Oscar for "The Dark Knight" thanks to his landmark portrayal as the Joker.
Damon, meanwhile, starred in several films around that same time (including "The Informant!" and "Invictus"), though it's clear he would've appeared in "Milk" if the timing had worked out. Interestingly enough, however, Damon and Brolin wound up crossing paths on screen just a couple years later in the Coen Brothers' 2010 remake of "True Grit" (in which they starred opposite Jeff Bridges). The pair also technically appeared together in 2018's "Deadpool 2," in which Damon made a cameo as a "redneck" (with Brolin starring as the time-traveling Cable).