The Essential Matt Damon Movies

Matt Damon is one of our most important leading actors working today, not only because he's a talented performer, but also because he's been on both sides of the camera. He's produced and written films, notably writing and starring in the award-winning Good Will Hunting.

Christopher Nolan's The Odyssey opens tomorrow, and Matt Damon has spent the whole press tour saying the same faintly ominous thing about it. He told GQ the shoot felt nostalgic, like the movies he came up on, and that he knew it was "the last chance I was going to have to do something like this."

For what it's worth, Nolan isn't having it. He told Variety there's "a defeatist aspect of viewing it that way that I don't agree with."

I have no idea which of them is right, and I doubt we'll know for another decade. But the argument sent me back through Damon's filmography, one rich with advice we can take away. How do I get hired? What do I do when the star opposite me is eating the movie? Join us on this... er, odyssey.

Good Will Hunting

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We already mentioned this classic, but we'll start the list with it because it's just that good. Nobody was casting Damon and Ben Affleck in anything good, so they wrote themselves parts, and the process took years. Thousands of pages. Drafts hammered out on drives between Boston and LA.

There was a version where Will gets beaten to death with a baseball bat, which, as an ending, is a big choice. By the time it sold, the money had stopped mattering.

"We never cared about money—we wanted to be in the movie. That was our only thing," Damon said in Boston Magazine's oral history. "That was our big ask."

The two guys who had just spent years on a script handed it to Gus Van Sant and stepped back.

"Look, man, you are the director. This was our baby, it's yours now, go and do whatever it is you have to do," Damon said, describing the handoff for Film Scouts.

We put the bench scene on our list of the best movie monologues. What's your favorite part of this one?

The Talented Mr. Ripley

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So Damon wins an Oscar, and every studio in town wants to hand him a hero role, and instead, he goes off to Italy to play a murderer.

Anthony Minghella cast him because audiences liked him. Tom Ripley only works if you catch yourself hoping he gets away with it, which, God help us, we always do.

Damon has talked about the prep in a way that takes all the mystique out of it.

"I have to run six miles a day, I can't eat this food, I have to learn how to play the piano, that's just a checklist, a shopping list of things you have to do every day," he said in an interview via ReelRave.

He lost about 30 pounds because the script needed him to covet Jude Law's body, an assignment he seems to have found funny.

"I was supposed to look like Jude Law, which is impossible in the first place: it's like being told you have to look like Alain Delon. I had to at least make my body look like his," Damon told Kaufmann.

Ocean's Eleven

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Damon wasn't anybody's first idea for Linus Caldwell. Johnny Depp was considered, then Mark Wahlberg was cast and left to go do Planet of the Apes (which, thank goodness, sorry). George Clooney told the story at the 2023 TCM Classic Film Festival with rather less tact than that.

"Some very famous people told us to f*ck right off: Mark Wahlberg, Johnny Depp. There were others. They regret it now. I regret doing f*cking Batman," Clooney said, per IndieWire.

Damon picked up the scraps and then played the kid, the one everyone else in the room outclasses, a hot young star in a room with comedy legends like Carl Reiner.

He's never pretended otherwise. "Ask anybody on the street which actors starred in the Ocean's movies, and they'll tell you it was George [Clooney] and Brad [Pitt]. I'm 'support' in Ocean's," Damon said in an interview with The Times.

Watch the movie with that in mind, and you can see him doing it on purpose. Linus is nervous, so that Clooney and Pitt get to be unbothered, and the whole breezy machine runs on somebody being willing to sweat. If you're building an ensemble, somebody has to take that job, and it's usually the person secure enough not to need the win. I love this one because few films get to be true ensemble pieces anymore. Too many big heads, I guess.

The Bourne Identity

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This one was fraught, suffering four rounds of reshoots, a release date shoved back three separate times, and Doug Liman at open war with Universal.

"The word on Bourne was that it was supposed to be a turkey," Damon told GQ in 2012. "It's very rare that a movie comes out a year late, has four rounds of reshoots, and it's good. So Tony Gilroy arbitrated against himself to not be the writer with sole credit."

Liman didn't cast him for the abs.

"In Matt's hands, I could give Bourne a really dark past, and you would still root for him," Liman told The Hollywood Reporter.

The Departed

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Damon got this job because Brad Pitt asked him to do it. Damon said in GQ's Iconic Characters interview:

"I remember, we were shooting Ocean's 12, and Brad came up and said, 'Hey, do you want to be in a Martin Scorsese movie?' Because Brad, I don't know if you know, produced that. Brad was going to play either Leo or my role, I can't remember which one. I guess they had spoken to Marty, and Marty was like, 'No, I'd like to have Matt.' I thought Brad was joking. What actor do you ask that question of? You're like, 'Shut up, man.' He's like, 'No, I'm actually serious.' And then he handed me the script and it was fantastic."

He's the mole who can't win a fight, can't finish anything. It's one of the most complex villains we've seen in recent cinema. We got into the story in our filmmaking lessons from The Departed.

What's your favorite Matt Damon movie?