Jack Nicholson as Frank Costello and Matt Damon as Colin Sullivan in The Departed.

Top 10 Best Matt Damon Movies, From Math Genius to Career Criminal

Alas, Stuck on You did not make the cut.

Matt Damon is among the most instantly recognizable movie stars, and 2023 will bring us two new performances that might be some of his best. He’ll serve as one of the leads and co-writer in his best friend Ben Affleck’s new movie Air Jordan, and has a role in Oppenheimer, Cristopher Nolan’s newest film. Since he appeared on the cinema screen as the bad guy in 1992’s School Ties, Damon has done some incredible performances, and here are his 10 best.

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10) Courage Under Fire

Matt Damon as Specialist Andrew Ilario in Courage Under Fire
Image Source: 20th Century Fox

Courage Under Fire tells the story of Nathaniel Serling (Denzel Washington), tasked with deciding if Captain Karen Walden (Meg Ryan) should be the first woman to receive the Medal of Honor after she died on a mission in Iraq. 

The movie uses a Rashomon-esque structure to show how every one of the survivors remembers what happened the day Walden died, and how their different versions might hide some troubling truths. Both Washington and Ryan are excellent, especially the rom-com queen in a role much more fierce and action-packed than what fans were used to from her.

Damon plays military medic Andrew Ilario, who has developed a heroin addiction since he came back from the war. His role is small, but one that makes a mark, as he lost 40 pounds for it, becoming all bones; a sad, ghostly figure, still haunted by what happened in Iraq. The role could’ve been a forgettable one, but Damon’s performance and commitment make it one of the best in the film. In a movie with both Denzel Washington and Meg Ryan, that is saying something.

9) Ford v Ferrari

Matt Damon as Carroll Shelby in Ford v Ferrari
Image Source: 20th Century Fox

This movie, directed by James Mangold (Logan), is about race car driver turned car designer Carroll Shelby (Damon) and pilot Ken Miles (Christian Bale), as they try to build a vehicle that can win the 24 Hours of Le Mans. The Ford Motor Company hires Shelby, intending to finally beat Enzo Ferrari and his racing team in the renowned competition.

Ford v Ferrari is a two-hander between Damon and Bale. They play a pair of characters who couldn’t be more different and who don’t see eye to eye, but through hard work and being good at what they each do, they start to respect each other, as both share the same objective.

Bale’s role is flashier, but without Damon’s smart, charismatic, gritty performance, the movie wouldn’t work. It’s through his character’s eyes that you understand why this race is so important to him and the Ford Motor Company. With a simple look, Damon can transmit how much Shelby misses racing, and how he’s adapting his expectations in the new role — one which might give him a different, rewarding career if they’re able to topple the Italian giants.

8) The Informant!

Matt Damon as Mark Whitacre in The Informant!
Image Source: Warner Bros. Pictures

Steven Soderbergh’s The Informant! tells the story of informant Mark Whiteacre (Damon), a rising star at an agricultural company in Illinois, who becomes a whistleblower for the FBI when they start investigating price-fixing claims by the company. Although this description might make it look like a movie closer to The Insider, the truth is this film is a satirical comedy with a maniac at its center.

Soderbergh has always done unique, out-of-left-field films, and this might be his weirdest ever. Whiteacre is the ultimate unreliable narrator; a man with bipolar disorder that causes all the trouble he gets into of his own volition. He grows crazier the more addicted he gets to the thrill of being a spy, to the point he starts lying to ensure the FBI keeps him employed.

Matt Damon’s performance here is something he has never done before, as he plays anxious, creepy, cowardly, dumb, and quirky; someone who has drunk his own Kool-Aid and relishes in it. Whitacre calls himself 0014 because he’s “twice as smart as 007”. This absurd, over-confident comment is the perfect way to explain the character, and the panache with which Damon plays it explains why he was nominated for a Golden Globe for the role.

7) Rounders

Edward Norton as Worm and Matt Damon as Mike McDermott in Rounders.
Image Source: Miramax Films

Mike McDermott (Damon) is a great poker player who leaves that life behind after he gets cleaned up by Russian mobster Teddy KGB (John Malkovich). When his best friend Worm (Edward Norton) is released from prison, Mike goes back to the high-stakes poker life so he can save his buddy from getting killed by a loan shark to whom he owes a large sum of money.

Rounders offered an unprecedented look at the game itself, becoming a cult classic among poker fans, and it was the type of project that proved Damon and Norton were leading man material. They’re surrounded by an incredible cast of supporting characters: Malkovich, John Turturro (Barton Fink), Gretchen Mol (Boardwalk Empire), Famke Janssen (X-Men), and Martin Landau (Crimes and Misdemeanors).

This is one of Damon’s earliest lead roles, and he proved he could do it with his eyes closed. His performance is magnetic, playing a smart guy between the world of law and poker, who knows how good he is, and his charisma and assuredness show as the movie goes on. His face when he loses all his money in one hand at the start of the film is incredible, and it should appear in the Urban Dictionary under “losing your shirt”, as it showcases that sensation spectacularly well.

6) The Ocean’s Movies

Matt Damon as Linus Caldwell in Ocean's Eleven.
Image Source: Warner Bros. Pictures

Danny Ocean (George Clooney) plans to rob three Las Vegas casinos in a single sweep, so he hires a team of thieves, where everyone has their expertise, to help him do it. Damon plays Linus, the third in command after Danny and Rusty (Brad Pitt), who everyone treats like a kid. His character gets more to do with each sequel.

This Soderbergh trilogy is pure fun. It has incredible, imaginative heists, especially in the first movie, exuding a sense of style and appeal. The cast is incredible; between the three films it has Clooney, Pitt, and Damon, alongside Julia Roberts, Catherine Zeta-Jones, Al Pacino, Andy Garcia, Elliot Gould, and Don Cheadle, to name a few. 

Damon’s reverence for his older co-stars made him the perfect Linus, as he always looks up to them and wants to be part of the leadership group; a dynamic that might’ve been pretty real for the trio of stars. His character gets more to do in the second and third movies, and his scene with Julia Roberts as Tess, trying to make her pass as the real Julia when they meet Bruce Willis while trying to steal a golden egg, is farcical comedy perfection. 

5) The Departed

Matt Damon as Colin Sullivan and Leonardo DiCaprio as Billy Costigan in The Departed.
Image Source: Warner Bros. Pictures

Martin Scorsese’s The Departed tells the story of two covert men on opposites sides of the law: Colin (Damon) is a crooked cop secretly protecting mob boss Frank Costello (Jack Nicholson), while Billy (Leonardo DiCaprio) is an undercover agent who has infiltrated Costello’s gang with the intent of bringing him down. 

The film might be a remake of Hong Kong hit Infernal Affairs, but Scorsese makes it his own and creates one of his best films of this century. Every actor comes with their A game, having memorable performances, from Damon and DiCaprio to Nicholson (in an unhinged performance if there ever was one), Mark Wahlberg, Martin Sheen, Vera Farmiga, and Alec Baldwin.

Damon doesn’t play sleazy douchebag that much, but when he does, he does it perfectly. This character might be the other side of the coin of Good Will Hunting, as his performance here is rotten at its core, but he’s able to hide it from most people. Colin is an evil, self-interested guy without a moral compass who is only looking for himself and his mob boss, consequences be damned, and the actor plays it perfectly.

4) The Bourne Movies

Matt Damon as Jason Bourne in The Bourne Identity.
Image Source: Universal Pictures

Jason Bourne (Damon) wakes up in a fishing boat with two bullets in his body and no memory. From there on, understanding who he is becomes his main mission while also trying to unravel the mystery of Project Treadstone.

Bourne Identity, the first movie in this action franchise, still feels the best, as it has a beautiful Before Sunrise-esque story wrapped inside a thrilling action movie. The car chase with a Mini through the streets of Paris might’ve greenlighted The Italian Job by itself. The second and third entries, directed by Paul Greengrass, are remembered for their particular style of action. His direction changed how these scenes were shot, giving much more realism with its hand-held movement camera, and spectacular fight-with-whatever-you-have-at-hand choreography.

Damon’s performance as a badass was surprising at first, as he’s always been a more cerebral actor, but the non-conventional story of the first film gave the ins into this character, creating his first franchise that allowed him to take greater risks on other roles.

3) The Martian

Matt Damon as Mark Watney in The Martian.
Image Source: 20th Century Fox

Mark Watney (Damon) is an astronaut who gets stranded alone on Mars after a sandstorm separated him from his crew while they’re leaving the planet. He must think of a way to survive on the red planet while trying to communicate with NASA so that someone might rescue him.

Ridley Scott still has it, even in his 80s, as this movie proved in 2015. The Martian is a bet on science and technology, solving problems, and believing in the good of humanity. Scott’s direction and Damon’s performance are what make this film a good one, while also having some interesting supporting roles from actors as diverse as Chiwetel Ejiofor, Benedict Wong, Mackenzie Davis, Jessica Chastain, and Sean Bean. Special mention goes to Donald Glover, who in three small scenes, creates one of the most fun characters in the whole film.

Watney is smart and has boy-scout looks and attitude, and audiences can’t help but root for him. The same is true of Matt Damon. The character spends most of the movie isolated, and only a big movie star can support being the center of the film so much, as it’s them all alone, all the time, in a one-man show. Damon passes the test with flying colors, imbuing the character with anguish, frustration, and the worry of someone stranded alone on a planet that wants to kill him. Not everything is negative though, as Watney is also able to make people laugh, celebrate his small victories, and succeed with his ideas long enough to be rescued.

2) Good Will Hunting

Matt Damon as Will Hunting in Good Will Hunting.
Image Source: Miramax Films

Will Hunting (Damon) is a Boston screwup working as a janitor at MIT. When he cracks an unsolvable math problem, it becomes obvious that he’s a math prodigy. The problem is that Will keeps getting in trouble as he has anger outbursts, and he’s scarred from his youth. Sean (Robin Williams), the college therapist, might be the only one who can help him let go of his troubled past.

25 years ago, Good Will Hunting changed Matt Damon and Ben Affleck’s careers forever. The duo had written the movie (landing them an Academy Award for best original screenplay) and starred in it, becoming masters of their destiny. By writing roles for themselves where they would shine, they made Hollywood aware of their talents. This film was their break-out hit, and they haven’t stopped working since.

Damon played the leading role, while Affleck portrayed his best friend, and both performances were great. The Ocean’s actor showed Will Hunting as a guy with a tough exterior and a sensible good heart. Having written him first-hand, Damon understood the character, knowing how to show his hurt, fury, smarts, and protectiveness of his friends and life, perfectly. He received his first Best Actor Oscar nomination for the role, and it was well deserved.

1) The Talented Mr. Ripley

Gwyneth Paltrow as Marge Sherwood, Jude Law as Dickie Greenleaf, and Matt Damon as Tom Ripley in The Talented Mr. Ripley.
Image Source: Paramount Pictures

Tom Ripley (Damon), is approached by a rich magnate who believes Ripley knows his son Dickie (Jude Law) and asks him to bring him back from Italy. Once Ripley meets Dickie and his girlfriend Marge (Gwyneth Paltrow), he falls in love with their lifestyle and does anything in his power to stay in that world.

As we said while talking about The Departed, bad-guy Damon is the most interesting Damon, and this film is no different. Although The Talented Mr. Ripley is a study of someone who becomes a sociopath, the actor infuses the character with enough tenderness, confusion, and love to be seen as an antihero. That’s until his worst impulses and desperation sink in, and he becomes someone who will betray, lie, or kill anyone to keep his new status. 

The whole cast is great: Law is all charisma as Dickie, Paltrow gives dignity and personality to a character that could’ve been a nothing part, Cate Blanchett shows the first clues of why she would become a star, and Philip Seymour-Hoffman goes all in as the douchey, horny, Freddie Miles.

Damon’s performance is one of his most layered ever, showing both his desire to fit in and his ambition to climb the social ladder. It’s for all those reasons this could be considered his best acting ever and seeing the list, that’s saying something.

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Image of Rafa Boladeras
Rafa Boladeras
I'm a writer who loves Wes Anderson movies, shows like The Wire, How I Met Your Mother, or Friday Night Lights, and has published a couple of books.