It has been exactly 20 years since Matt Damon and his childhood friend Ben Affleck launched their careers into high gear when they wrote the screenplay for “Good Will Hunting.” That film would bring them an Academy Award for Best Original Screenplay and a Best Actor Oscar nomination for Damon. The press and praise the film received launched both actors into a steady stream of work for the next two decades.
Damon has had a prolific year in 2017 with two end-of-year film releases “Suburbicon” (directed by good friend George Clooney) and “Downsizing” (helmed by awards magnet Alexander Payne). Earlier this year his film “The Great Wall” met with some protests because of it having a white actor in the lead of a story set in China (a fact jokingly mentioned by faux-enemy Jimmy Kimmel when he hosted the Oscars).
But the lack of great success in 2017 will probably just go down as an anomaly for Damon, who has had one of the most consistent and acclaimed careers of recent years. To date Damon has earned nominations five times at the Oscars, seven times at the Golden Globes and six times at the Emmys, either as actor, writer and producer of various projects. Tour our photo gallery with a look back at Damon’s 15 greatest films.
15. ROUNDERS (1998)
Damon plays a law student who gets involved in the world of underground poker tournaments. While the film met with mixed results Damon gives a strong performance as his character finds himself torn between a career in law and the love of his girlfriend.
14. THE BROTHERS GRIMM (2005)
While Heath Ledger gave the more transformative performance as the shy and awkward younger of the two Grimm brothers, Damon holds his own as the more self-assured and confident of the two. The complicated relationship of the two brothers who would go on to create the famed Grimm’s Fairy Tales is nicely detailed and Damon manages to show a wounded side of his character in regards to his sister’s death.
13. OCEAN’S TRILOGY (2001, 2004, 2007)
Damon played the pick pocket Linus Caldwell in this highly successful series of films which he made with his friends George Clooney, Brad Pitt and Casey Affleck. These films don’t really challenge Damon’s range to much but he clearly seems to be enjoying himself as do most of the all-star casts of the three films.
12. THE RAINMAKER (1997)
A few weeks before “Good Will Hunting” opened, Damon had the lead role in this adaptation of a John Grisham novel. Damon is earnest and likable as a young lawyer who stumbles into a ground breaking legal case.
11. SCHOOL TIES (1992)
Damon’s first major role was in this story of anti-Semitism at an elite private school in the 1950s. Damon who has made a career of usually playing likeable characters is cast against type here as the villain of the film. He is smarmy and bratty as the student who outs the lead character as being Jewish.
10. THE BOURNE SERIES (2002, 2004, 2007, 2016)
Damon latched on to a highly successful franchise when he took on the character of former CIA agent Jason Bourne. The films vary in quality but Damon brings an intelligence and relatability to a character that could have come across as a standard action hero in lesser hands.
9. TRUE GRIT (2010)
The Coen brothers took on a big challenge when they chose to remake the classic John Wayne western that won him the Best Actor Oscar in 1969. Jeff Bridges took the Wayne role and also received Oscar recognition with a Best Actor nomination. Damon took on the role played by singer Glen Campbell in the original film.
8. SAVING PRIVATE RYAN (1998)
It could be argued that “Saving Private Ryan” is the greatest film Matt Damon has ever been in but this list is ranking the best Damon performances so it ends up a little lower than people may have expected. Damon appears later in the Steven Spielberg film as the title character of the film, a soldier whose three brothers were killed in action on Omaha Beach during the World War II battle known as D-Day.
7. COURAGE UNDER FIRE (1996)
This is one of Damon’s best early roles but surprisingly it is a film that almost drove him out of the acting profession. Damon plays a gulf war veteran who is so traumatized by his experiences that he develops a heroin addiction upon his return home. Damon lost 40 pounds to play the scenes of addiction in the film.
6. SYRIANA (2005)
Even though walked away with a Best Supporting Actor Oscar, Damon also shines in the film as an ambitious energy analyst who befriends an Arab Prince and oil tycoon. He is particularly riveting in the later scenes of the film and especially in a shocking moment when his character is involved in a car explosion.
5. THE DEPARTED (2006)
This film was the one that finally won Martin Scorsese a Best Director Oscar. It also took the Best Picture award that year and the film offers Damon one of his most challenging roles. He is paired with Leonardo DiCaprio as two young men both involved in various ways in both organized crime and law enforcement.
4. INVICTUS (2009)
Damon received his second acting Oscar nomination (as Best Supporting Actor) for this true story of how a soccer team victory in South Africa helped heal the racial wounds that country suffered through under apartheid.
3. THE MARTIAN (2015)
Damon won a Golden Globe as Best Comedy Actor for this story of an astronaut stranded on Mars and unable to communicate with anyone to show he is still alive. He does great work in scenes that don’t have any other actors in them and require his star quality alone to sustain audience interest. Damon received his third Oscar acting nomination for this film.
2. GOOD WILL HUNTING (1997)
Damon and Affleck inspired generations of aspiring actors to write their own material when they won an Oscar for Best Original Screenplay. He also received a Best Actor nomination for his role as a janitor who turns out to be a math genius. Blocked from pursuing his natural talents due to childhood abuse Damon’s character is helped by a psychologist played by Robin Williams (Oscar for Best Supporting Actor).
1. THE TALENTED MR. RIPLEY (1999)
Damon was robbed of an Oscar nomination for “The Talented Mr. Ripley” easily the most complex role the actor has ever taken on. He is just riveting in this story of an aimless young man with identity issues who is employed by a wealthy tycoon to go to Italy and find the tycoon’s wayward son Dickie (Jude Law). Damon’s character of Ripley is a compulsive liar who both falls in love with and also wants to become the ultra-smooth Dickie.
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