Matt Damon’s Ten Best Movie Roles

Matt Damon is definitely smack dab in the prime of his acting career. Fresh off an Oscar nomination for Invictus, he is hotter than ever. With upcoming projects with the Coen brothers and Clint Eastwood, Damon is approaching megastar status in Hollywood, if he wasn’t already there.

His latest, Green Zone, reunites him with Bourne series director Paul Greengrass. The buzz has been positive, so another hit could be in store for the Academy Award winner. Perusing his filmography, I was reminded how many excellent performances Damon has delivered over the years.

It wasn’t easy to narrow them down, but here are what I think are his ten best roles. (NSFW material and SPOILERS ahead.)

10. Charlie Dillon in School Ties

Damon doesn’t play bad guys very often, but before he became a big screen hero he was young Charlie Dillon, a racist prick who loses his shit after Brendan Fraser’s David Greene steals his girl and starting quarterback job. In his first major part, Damon showed he had the skills to hang.

9. Ilario in Courage Under Fire

Damon went method and dropped weight to portray a drug addicted Desert Storm veteran with a deep dark secret. His scenes are some of the most dramatic in the film, and he more than holds his own going up against Denzel Washington. Despite being a secondary character, he still shines.

8. Pvt. James Ryan in Saving Private Ryan

Although he wasn’t given many scenes in Steven Spielberg’s war epic, Damon didn’t disappoint. Whoever played the titular character in this one was under pressure. The audience and the characters had to believe Ryan was worth saving. Damon’s natural likability made him a good choice.

7. Linus Caldwell in Ocean’s 11, 12 and 13

Matt is a third wheel to Clooney and Pitt, but that doesn’t prevent him from overshadowing the two matinee idols. He also flexes his comedic muscles by being the butt of several jokes. Versatility separates the greats from the pack. Damon proved he belongs in select company.

6. Mark Whitacre in The Informant!

Complete with beer gut and creepy mustache, Damon takes his comic chops to another level in this underrated turn. Whitacre is looney tunes, but not in a Travis Bickle way. Damon plays for laughs rather than scares. This movie gets better with repeat viewings.

5. Mike McDermott in Rounders

Again, Damon goes head-to-head with a pair of acting heavyweights: Edward Norton and John Malkovich. Matty learned the art of cards to prepare for the role and even participated in the World Series of Poker. His climatic sitdown with Teddy KGB is memorable.

4. Colin Sullivan in The Departed

He returned to the role of villain in Martin Scorsese’s Oscar winner for Best Picture. DiCaprio and Nicholson received most of the pub, but Damon kills portraying a mobster who infiltrates the Massachusetts State Police. Pulling off a realistic double agent is tough. Matt makes it look easy.

3. Tom Ripley in The Talented Mr. Ripley

Damon should have gotten a Best Actor Oscar nod back in 1999 for his stunning portrayal of psychotic leech Tom Ripley. His ability to garner both sympathy and hatred is impressive. Ripley is a pathetic loser, but he’s also a calculating murderer capable of switching personalities at a moment’s notice.

2. Jason Bourne in The Bourne Trilogy

It’s the role that transformed Damon into an international action star and once again revealed his talent to wear different acting hats. Clooney and Nic Cage have flopped in similar spots. Not Damon. He adds a credible vulnerability to the conflicted rouge assassin, Jason Bourne.

1. Will Hunting in Good Will Hunting

Matty traverses the emotional spectrum as the damaged genius Will Hunting. Tough guy, romantic lead, loyal friend, self-loathing smartass, frightened little boy. He covers them all in a script he co-wrote with Ben Affleck and snagged a Best Original Screenplay Oscar.