Matt Damon has had one of the more interesting leading man careers of most of his peers. Damon had a few acting credits to his name before he found his big breakthrough with Good Will Hunting, a film he co-wrote with his best friend Ben Affleck that led to the duo winning the Academy Award for Best Original Screenplay. Damon earned his first of two acting Oscar nominations for his lead performance, and it would begin a film career that has seen him work with several A-list directors, as he has eased comfortably into major franchise releases as well as smaller independent projects.
Damon has movie star qualities with character actor sensibilities that have made him one of the stronger actors of his generation, and yet, it still feels like he’s a bit underestimated. This weekend, he leads Christopher Nolan’s The Odyssey, a film that further solidifies not only his leading man status but his abilities as an actor who can bury himself into a role when necessary. As he graces the big screen once again, this presents the perfect opportunity to nail down his five best performances ever!
Honorable Mention: Loki in Dogma (1999)
Following Good Will Hunting, Damon appeared in Steven Spielberg’s Saving Private Ryan, the poker drama Rounders, and the thriller The Talented Mr. Ripley, so it was a breath of fresh air to see him switch things up, reuniting with his buddy Ben Affleck in Kevin Smith’s controversial religious fantasy comedy film, Dogma. Also written by Smith, Dogma is the fourth film in the View Askewniverse and follows two fallen angels (portrayed by Damon and Affleck) who plan to take advantage of an alleged loophole in Catholic dogma that will allow them to return to heaven after being cast out by God. However, there’s a catch.
Should they do that, since existence is founded on the principle that God is correct in all matters, it would mean that God was wrong, which would undo all creation. You get a taste of Damon and Affleck’s easygoing humor with each other during the lighter moments of Good Will Hunting, and that’s dialed up to a ten watching them riff off each other as Loki and Bartleby. Their banter as the exiled angels represents some of the best moments of the film, and Damon finds added humor in his conflict as Loki, with his existential crisis being both hilarious and, at times, sympathetic.
He’s a fallen angel trying to find his place in the world, and it’s all wrapped up in Smith’s signature whip-smart dialogue that Damon has no problem conveying. Whenever he and Affleck are on screen, Dogma truly pops, and since the latter was already no stranger to Smith’s universe, Damon’s ability to fit right into it makes him stand out even more.
5. Colin Sullivan in The Departed (2006)
Damon has primarily been known to play heroic or sympathetic characters, so it was great to see him subvert those expectations in The Departed as Colin Sullivan, a figure disguising himself as a hero as he hides truly sinister intentions. Directed by Martin Scorsese and from a screenplay by William Monahan, The Departed is a remake of the 2002 Hong Kong film Infernal Affairs and also draws inspiration from real-life people such as corrupt FBI agent John Connolly, the Winter Hill Gang, and crime boss Whitey Bulger. In the film, which is set in South Boston, Irish Mob boss Frank Costello (Jack Nicholson) inserts Colin Sullivan (Damon) as a spy within the Massachusetts State Police, as the law enforcement plants undercover state trooper Billy Costigan (Leonardo DiCaprio) within Costello’s organization to infiltrate it.
The Departed is a stacked ensemble with many fantastic actors, but Damon more than holds his own using his Boy Scout charm and natural likability to mask a ruthlessness that he has no problem easing into. Damon portrays the duality of the character beautifully, able to easily present an upstanding member of law enforcement, all while slipping effortlessly into portraying a snake in the grass who is betraying his badge. The brilliance in his performance is how controlled and deliberate it is. He’s not a foaming-at-the-mouth villain since he has to maintain his own cover, but Damon has moments when his entitlement as a man of the law blurs with the power he has from being groomed by the mob, where you see a hint of rage whenever someone questions his authority. It’s also wonderfully juxtaposed with DiCaprio’s performance.
Colin is more polished and calculated because he has been adequately prepped for his deception, while Billy is constantly on edge and one step away from paranoia. Damon’s role in The Departed is a classic example of an actor playing with the tropes of his persona to portray someone who is less than stellar as a human being.
4. Mark Watney in The Martian (2015)
It’s no easy task to carry a film primarily on your own, but Damon more than proved his worth with his Oscar-nominated turn in The Martian. Directed by Ridley Scott and from a screenplay by Drew Goddard, The Martian is based on Andy Weir’s 2011 novel of the same name, and follows Mark Watney (Damon), an astronaut trying to survive on Mars after being left behind, and the efforts employed by NASA to bring him home. Even though The Martian features notable names in its supporting ensemble, The Martian is pretty much Damon’s show, and he leads it with incredible charm and a relatable humanity that allows the film to be a more human story that isn’t just rooted in the science of it all.
As Mark, Damon showcases many facets of his personality, from his humor to his resilience, all while making the character completely grounded without resorting to unnecessary action-hero cliches. At the end of the day, Mark is a normal man thrust into an impossible situation who has to use his wit and intellect to power through. It’s not always perfect, as Mark’s trial-and-error approach to survival hits roadblocks, but it’s Damon’s everyman charm that motivates the audience and makes them believe that he can get through this. Damon is at his best here during his video logs that not only drive the narrative but also provide a window into who Mark is as a person.
He doesn’t have the benefit of bouncing off other actors in the flesh and in real time to help bolster his performance. The Martian only solidified that one of Damon’s strongest attributes as an actor is that he makes you buy every moment he delivers as a character, and in the case of this film, those moments make the audience root for him from start to finish.
3. Tom Ripley in The Talented Mr. Ripley (1999)
Much like he would later exhibit in The Departed, Damon utilizes a boyish charm yet vulnerability that makes his chilling turn on a dime into a troubled sociopath in The Talented Mr. Ripley one to remember. Written and directed by Anthony Minghella, The Talented Mr. Ripley is based on the 1955 novel of the same name by Patricia Highsmith and follows Tom Ripley (Damon), an American con artist who is sent to Italy, via his own deception, to convince the rich and spoiled Dickie Greenleaf (Jude Law) to return home. However, things don’t go as planned once Tom becomes dangerously obsessed with Dickie and has grown attached to his lifestyle. Law won most of the attention for The Talented Mr. Ripley, including a much-deserved Best Supporting Actor Oscar nomination, but none of the film works without Damon’s calculating and duplicitous performance.
As Tom, Damon engages the audiences’ sympathy because you can tell he’s a lonely soul who finds no value in himself, which is why he desires the lives of others. At the same time, this is all done to disarm you because even though that vulnerability is always on the surface, the desperation of his obsession, which only grows more callous as the film goes along, also presents a man who has a level of ruthlessness and psychological derangement that might be who he is at his core. Damon makes you bounce back and forth regarding how you feel about Tom.
As his misdeeds become more dangerous and lives are ruined in his wake, he still has an innate ability to tug at our sympathies. This is conveyed during Damon’s final scene of the film, which still stands as some of his best work. Tom has found a way to fully live Dickie’s lifestyle as himself and heads off to Greece with a man named Peter (Jack Davenport), a friend of Marge (Gwyneth Paltrow), the woman who was involved with Dickie before Tom infiltrated their lives. Tom and Peter have become lovers, and it seems like Tom will be able to live a “real” and happy life until a moment gives Peter doubt, and he demands answers.
It’s in this moment that Tom’s happiness is threatened again, and after apologizing for his deception, he begins to cry and strangle Peter through his sobs. Most of this happens off-screen, and you can only hear the dialogue, but Damon’s portrayal of Tom’s pain and then the gradual shift to his reluctant violence is a palpable moment that lingers with you long after the movie is over.
2. Will Hunting in Good Will Hunting (1997)
Perhaps because he co-wrote the screenplay and the film is set in an area he was familiar with and accustomed to, Damon’s performance in Good Will Hunting still electrifies because of how lived in it feels. Everything about his choices is authentic, and there is a rawness that gives his journey much of its power. Directed by Gus Van Sant and from a screenplay Damon co-wrote with Ben Affleck, Good Will Hunting is set in Boston and follows Will Hunting (Damon), a troubled soul but self-taught mathematical genius who works as a janitor at MIT. After his talent is discovered by professor Gerald Lambeau (Stellan Skarsgård), Will agrees to study under him in order to avoid jail while also attending therapy with psychologist Sean Maguire (Robin Williams), which makes him confront past traumas.
There are so many layers in Damon’s performance as Will Hunting, and he navigates them like a pro. It’s a role where his masculinity and life-style amongst his blue-collar friends only masks a deep-seeded vulnerability and pain where being tough is a shield to protet him from genuine human emotions and relationships that will challenge him. He rejects emotional intimacy, even though he longs for it. He rejects his natural gifts only because he’s afraid of failing. It’s a duality that Damon excels at here because he finds the humanity in all of it. That’s probably why the character is relatable to so many.
Putting up walls as a defense mechanism, especially for men, is so commonplace when they’re masking past traumas, and Damon plays that truth through the writing and his impeccable performance. It’s an early sign of his natural charisma, but also of how powerful he can be when he digs deep. Whether it’s during his scene with Skylar (Minnie Driver) after she calls him out for being scared about moving to California with her, or during the iconic “it’s not your fault” scene with Robin Williams, Damon makes you feel like you’re going through this emotional exorcism with him. It’s a performance that touches your heart because it’s genuine without a false moment in sight.
1. Odysseus in The Odyssey (2026)
Damon has called working on The Odyssey the best moment of his career, but also the most challenging and the most grueling. None of this was meant to generate sympathy or to suggest that the experience was difficult in a negative sense, but it was all to express how fulfilling this film was for him as an actor. As you watch Damon’s turn as Odysseus, you can see Damon’s fulfillment because his blood, sweat, and tears were given to every facet of this role, and you can tell by every single frame he’s in. It’s his grit and determination that shine through, but it’s ultimately the humanity that he discovers through this journey that makes this his best performance to date.
Written and directed by Christopher Nolan, the movie is based on Homer’s ancient Greek epic, The Odyssey, with the film chronicling Odysseus’ (Matt Damon) years-long journey home after the Trojan War, which also includes encounters with mythical creatures as his wife, Penelope (Anne Hathaway), has to fend off suitors who wish to take his place as the king of Ithaca. There is a level of commitment that Damon exhibits here that keeps the audience enthralled by Odysseus’ journey. It’s a physical performance for sure, but you also see the mental progression he goes through as he transitions from an arrogant warrior to a man humbled by his trauma and experiences on his long voyage home.
Damon is strong throughout, but he hits emotional highs during his encounter with the Sirens and as he confesses his guilt to Penelope (Anne Hathaway) for violating Zeus’s law and killing innocent Trojans during the war. This scene in particular resonates long after it’s over because Damon doesn’t go overboard with theatrics. He’s simply a man admitting his faults and displaying the pain and honesty of what all of this has taught him. Damon surely has more great work in him, but he’s most definitely outdone himself with this performance, and he has reached a new pinnacle of his talents.
The Odyssey is now playing in theaters nationwide.
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