The 2008 movie Matt Damon will never forgive himself for not making: “I was devastated”
What happens when you get Matt Damon, one of the best scripts he’s ever read, a character he’d do anything to play, and a director he knows and trusts implicitly? As it turns out, absolutely fuck all, if you’re Matt Damon.
There can’t be many things worse for an actor than having the part of a lifetime ripped away by circumstances that they can’t control, with Damon becoming the unfortunate victim of a domino effect that robbed him of a movie he was determined to make, and a potential Oscar nomination, to boot.
In Hollywood, scheduling conflicts are used as the go-to explanation for every movie that falls apart, gets pushed back, mothballed, or cancelled, while it’s become a handy excuse for actors who want to quit or back out, too. In Damon’s case, he was all in; it was one of his prospective co-stars who cost him big time.
It’s especially cruel because the film had been in development since 1991, and after finally escaping from cinematic purgatory to get in front of the cameras 17 years later, a last-minute reshuffle ruled out the Academy Award-winning Good Will Hunting screenwriter, and it’s haunted him ever since.
He was all set to reunite with that picture’s director, Gus Van Sant, who he’d worked with again on Gerry, to play Dan White in the biographical drama, Milk. Sean Penn was signed and sealed for the title role, which eventually won him an Oscar, but a scheduling snafu caused a ripple effect that crushed Damon.
“I was desperate to do the Dan White role,” the erstwhile Jason Bourne confessed. “It was one of the best scripts I’d ever read. Then it got pushed back because of Sean’s schedule, and I was devastated, even though it was only two weeks of work.” Two weeks of work that were enough to get Josh Brolin a ‘Best Supporting Actor’ nomination, though, which could have been Damon’s.
Thanks to Penn’s conflicts, the start date for Milk had to be delayed, with the first day of principal photography taking place in January 2008. Damon was set to begin Steven Soderbergh’s The Informant! in May, which usually would have freed him up for the two weeks necessary to shoot his scenes as White, but not in this case, since he had to gain 30 pounds for the role.
Not only had he first agreed to play the role of Mark Whitacre in 2002 when making Ocean’s Eleven with Soderbergh and had little time to pack on the beef before shooting, but the black comedy had already been pushed back so that he could star in Robert De Niro’s The Good Shepherd after Leonardo DiCaprio dropped out, and it wasn’t going to happen again.
It wasn’t his fault that he wasn’t able to milk Milk for a fortnight and possibly get an Oscar nomination for his troubles, but he’s too nice a guy to suggest that it was Penn’s, which technically it was.
