Matt Damon's Best & Worst Movie Roles: The Best

10. 'Dogma'

Who He Plays: Loki, an angel with a bad attitude, trying to get back into heaven (which would destroy Earth) in Kevin Smith's controversial comedy
Why It Ranks: In his first meaty comic role, Damon earns his wings. He and Ben Affleck are partners in crime, just a year after their 'Hunting' breakthrough.

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9. 'The Rainmaker'

Who He Plays: Law-school grad who sues an insurance company for denying treatment to a dying man
Why It Ranks: No one does "earnest good guy" like Damon, and with Francis Ford Coppola directing, he was the perfect David to the insurance companies' Goliath, inspiring outrage long before 'Sicko'.

8. The 'Ocean's' Trilogy

Who He Plays: Linus Caldwell, the youngest, least experienced, least confident of Ocean's gang ... wait, why was he recruited, again?
Why It Ranks: He's the butt of everyone's jokes, the screw-up whose parents have to rescue him. But he makes us laugh, plus he seduces Ellen Barkin. Pretty smooth for a bumbling rookie.

7. 'Syriana'

Who He Plays: Bryan Woodman, a U.S. businessman working for Big Oil in the Mideast
Why It Ranks: Damon is all business in Stephen Gaghan's take on global turmoil. Not even the death of his son can distract him from his real job -- making money. It's a quiet, confident dramatic performance.

6. 'Courage Under Fire'

Who He Plays: Heroin-addicted Gulf War vet Illario, knower of Meg Ryan's true battlefield fate
Why It Ranks: Damon dropped 40 pounds for the role, an impressive piece of method acting that caught the eye of legendary director Coppola, who just so happened to be casting 'The Rainmaker' at the time.

5. 'The Talented Mr. Ripley'

Who He Plays: Bi-curious psychopath Tom Ripley
Why It Ranks: Damon takes his everyman persona and gives it a chilling twist, going from charming to creepy in the blink of an eye. We loathe Ripley, we pity him ... and we salute Damon, whose unnerving performance gave us bad dreams for a week.

4. 'The Good Shepherd'

Who He Plays: Bright young CIA recruit, terrible husband
Why It Ranks: Damon's carefully understated portrayal of an enigmatic man so patriotic he'd rather creep around Soviet Russia than spoon Angelina Jolie was heralded by just about everyone except Oscar voters. We give those horn-rimmed glasses partial credit.

3. 'Good Will Hunting'

Who He Plays: The smartest man ever to mop for a living
Why It Ranks: You know the story: Damon and BFF Affleck became "overnight" sensations when their film grossed $138 million. Lost in the glow of their Oscar win for Best Screenplay was Damon's Best Actor nomination for sticking it to all the apple lovers out there.

2. 'The Departed'

Who He Plays: Det. Colin Sullivan, who's employed by the state of Massachusetts but married to the mob
Why It Ranks: He was overlooked at the Oscars, but Martin Scorsese's explosive masterpiece wouldn't have worked without Damon, who was superb -- corrupt, but still very human -- as the film's morally compromised center.

1. The 'Bourne' Trilogy

Who He Plays: Titular amnesiac spy Jason Bourne
Why It Ranks: Damon's work as a thinking man's action hero has cemented his status as a superstar and proved him to be one of the most versatile actors working today: He's charismatic, athletic and sympathetic in a way that other action icons (ahem, James Bond) are not.

Matt Damon's Best & Worst Movie Roles: The Worst

5. 'All the Pretty Horses'

Who He Plays: A 1940s cowboy who falls in love with Penélope Cruz
Why It Ranks: Director Billy Bob Thornton was forced to axe more than an hour from his four-hour long adaptation of Cormac McCarthy's novel, a move that he and Damon credit for the film's underdeveloped characters and general pointlessness.

4. 'Legend of Bagger Vance'

Who He Plays: A one-time golf star and now full-time drunk inspired to play again by a mysterious caddy named Bagger (Will Smith)
Why It Ranks: Despite Damon's best efforts (he learned to golf), Bagger's incessant adage-spewing and a schmaltzy love story make this a cinematic bogey.

3. 'Gerry'

Who He Plays: Gerry, not to be confused with the film's only other character, Gerry (Casey Affleck)
Why It Ranks: We appreciate art, but 103 minutes of watching the Gerrys wander lost through the desert, barely speaking? Six-minute-long close-ups of their sweaty brows? Were we wrong to want them to die already?

2. 'Stuck on You'

Who He Plays: Conjoined twin attached at the hip with Greg Kinnear
Why It Ranks: The Farrelly brothers found their first (and only?) major misfire with this exceedingly corny comedy not even Eva Mendes' breasts could salvage. Conjoined twins are supposed to be a helluva lot funnier than this, fellas.

1. 'The Brothers Grimm'

Who He Plays: Wilhelm (just call him Will) Grimm, in Terry Gilliam's fantasy take on the fairytale tellers
Why It Ranks: We can't blame Damon for biting into this one -- must've looked like a sure thing on paper. Even with Gilliam's vision and Heath Ledger as the other brother Grimm, the whole thing fell flat.

How They Began

Remember when Matt Damon played third fiddle to major stars like Brendan Fraser and Chris O'Donnell in 'School Ties'? We don't blame you, that was 1992.

See stars' early roles

Plus: Jason Bourne vs. James Bond

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