Matt Damon’s 10 Best Roles

The Oscar-winning star's career has taken some wild turns over the years

Matt Damon Best Roles
Matt Damon, photo by Lionel Hahn/Getty Images/Illustration by Steven Fiche

    Top Performances is a recurring feature in which we definitively handpick the very best performances from an iconic actor or actress. It has been updated for Matt Damon’s 52nd birthday.

    It’s not enough for Matt Damon to be conventionally attractive, or even physically imposing. He also has to be preternaturally intelligent, a savant capable of outwitting a Fields Medal-winning mathematician, a ruthless Russian card shark, or a millionaire casino owner, as the occasion may demand. This is the curious truth at the center of Damon’s career: Though he’s got all the looks you could hope for in a leading man, it’s what’s behind those steely blue eyes that keeps us coming back for more.

    Maybe it’s because he played a boy genius in 1997’s Good Will Hunting, then followed up that breakthrough role by starring as a shrewd underdog lawyer (Rainman), a wildly gifted poker player (Rounders), and a calculating psychopath (The Talented Mr. Ripley) for good measure. Or maybe this is simply what we expect from people who once attended Harvard University.


    In any case, Damon’s allure has as much to do with his brains as it does with his brawn. This is how the same man who played a nerdy pickpocket in Ocean’s Eleven could turn around and become the action star of his generation the very next year in The Bourne Identity. The frustrating part, at least for those of us who are mere mortals? Even when he’s playing an amnesic action hero who can’t remember his own name, Damon has no problem running intellectual circles around his adversaries.

    This much holds true in Damon’s 2015 sci-fi drama The Martian, just as it holds true in the latest iteration of the Bourne series, Jason Bourne. Both films touch on something essential about the actor that’s often overlooked: there’s always some aspect to his character’s identity that he prefers to keep to himself.

    While this might handicap a lesser actor, Damon uses it to draw us in, peppering his performances in The Martian and Jason Bourne with enough boyish charm and wise heroics to keep us, the audience, rooting from our seats. Can’t the same be said for the enigmatic schmuck Mark Whitacre in The Informant! or the bumbling, self-satisfied LaBoeuf in True Grit? Even The Departeds Colin Sullivan, who’s no hero, is motivated by something slightly beyond our grasp, whether it’s sexual impotence or a similarly private demon.


    All of this is to say that there’s more to Matt Damon than meets the eye, and so we’ve chosen to dig a little deeper into the actor’s 10 best performances in search of some answers. Of course, if you wanna read a real history book, read Howard Zinn’s A People’s History of the United States. Our list may not be quite as exhaustive, and it may not feature any mentally deficient puppets, but it should serve as a recap of Damon’s best moments.

    Collin Brennan

    10. SPC Ilario, Courage Under Fire (1996)

    matt damon courage under fire

    Damon had a small supporting role in the 1996 drama Courage Under Fire as Specialist Ilario, a Desert Storm medic turned heroin addict who took part in a tragic event that Denzel’s Washington’s Lt. Col. Nathan Serling is investigating, Rashomon-style. But despite his limited screen time, Damon makes an indelible impression and not just for his natural acting style and bedrock glimmer of star power. Physically, he is almost unrecognizable.

    In between the filming of the flashback scenes in combat and the present-day interviews with Washington, Damon took it upon himself to shed 40 pounds by undergoing a strict diet and exercise regimen, to the point that his health became severely compromised. Damon was put under medical supervision for several months after the shoot and for another year and a half took medication to correct the stress put on his adrenal gland.

    On Inside the Actor’s Studio, Damon said that he considered giving up acting after making Courage Under Fire because he nearly killed himself to play his part, and then after the film premiered, hardly anyone in the media mentioned him or his performance. Luckily Damon’s extreme measures did not go unnoticed by all, as Francis Ford Coppola picked Damon to star in The Rainmaker shortly after seeing the film, and Stephen Spielberg was so impressed by his performance that he would go on to cast him as his titular paratrooper in Saving Private Ryan.


    Damon’s Moment: In his final scene with Washington, Damon’s character tells him the truth about what happened. His gaunt face awash with sadness and regret, Damon hurts to look at as much as his story hurts to hear. And as excessive as the young actor’s commitment to method may have been for an auxiliary role, his account is a pivotal turning point in the film, and his delivery of it a masterclass. — Leah Pickett

    09. Mike McDermott, Rounders (1998)


    There are traces of Will Hunting in Mike McDermott, the poker-playing law student who flies too close to the sun. Both characters are boyish savants with supreme faith in their own talents, and both have a knack for getting themselves into trouble. The comparisons are inevitable, seeing as how Rounders hit theaters just a year after Good Will Hunting, but playing McDermott presented a new challenge to the young Damon.

    Rather than play the emotional loose cannon, he turns in a restrained performance as the straight man to Edward Norton’s wildcard ex-con, Worm. Speaking of restraint, Damon’s two high-stakes Texas hold’em games against Russian John Malkovich are a master class in understated acting. In both scenes, his face is a blank slate that betrays nothing, leaving us genuinely surprised when the cards turn over.


    Damon’s Moment: The opening scene, during which McDermott loses a huge hand to “KGB.” There’s no crying, no shouting, no shaking his fists at the sky. Damon merely stares ahead like a deer in headlights, his expression a cocktail of pain and disbelief. It’s a devastating moment, and we feel it right along with him. –C.B.

    08. Francois Pienaar, Invictus (2009)

    damon invictus

    To play South African rugby team captain Francois Pienaar in 2009’s Invictus, Damon underwent extensive training. First, in physique: Damon bulked up to play the “huge” athlete, with the help of director Clint Eastwood’s creative setups and camera angles to make him look taller as well.

    Second, in endurance: Damon received intensive coaching at the Garden Rugby Club under Chester Williams, who himself was a player on the 1995 South African rugby team portrayed in the film. And third, in voice: Damon honed his South African accent — along with Morgan Freeman, who plays post-Apartheid president Nelson Mandela — to passable, if not perfect, effect.

    Damon’s Pienaar is far from the most complex character that Damon has played. But his commitment to embodying the man, a child of racist parents whose moral compass and empathetic heart transcend his cultivation, is commendable. Interestingly, The Informant! and Invictus came out in the same year, and the characters that Damon played in each could not be more different.


    Damon’s Moment: Upon visiting the President’s prison cell, a scene filmed in the actual cell on Robben Island where Mandela spent the majority of his 27 years in solitary confinement, Pienaar steps inside, closes the door behind him, and lingers. He spreads his arms so that his fingers touch the wall. He stares out the window. His face glints with shame, sorrow, and awe.

    This scene informs and suffuses the climax, when at the height of the final match, Pienaar gathers his team into a huddle and points to the stadium that rises above, to the voices singing: “Do you hear? Listen to your country…This is it. This is our destiny.” — L.P.

    07. Mark Whitacre, The Informant! (2009)


    In an underrated film that few people saw in theaters, Damon disappeared into the role of Mark Whitacre, a tentative whistle-blower in the lysine price-fixing conspiracy of the mid-1990s whose story was detailed in a 2000 nonfiction book and adapted for the screen by Damon’s Ocean’s Eleven, Twelve, and Thirteen director Steven Soderbergh. The Informant! is a stylish, madcap caper with an arch approach to corporate greed; and as the layers of deceit peel back, so does Damon’s Whitacre, a vanilla schmuck so seemingly unsure of himself and his situation that he borders on naiveté.


    Pulling a reverse of his starvation-diet preparation for Courage Under a Fire, Damon packed on 30 pounds of pizza, beer, and hamburgers to more closely resemble the real-life Whitacre, a bumbling pawn who, with more than a little nudging from his wife, Ginger (Melanie Lynskey), learns how to play the game. Damon excels in playing unpredictable characters — his cameo as Dr. Mann in Interstellar being a prime example — and his Whitacre is, to paraphrase Seinfeld, an engima wrapped in a Twinkie.

    Damon’s Moment: The courtroom scene. In an interview with NPR, Damon said he was directed by Soderbergh to perform the lines to the judge as if he was accepting an Academy Award. He cited this as an example of “perfect direction,” but with another actor, the moment might have fallen flat. Instead, Damon takes his greasy charm and nails it to the wall. — L.P.

    06. Loki, Dogma (1999)

    damon dogma

    No, not that Loki, but wouldn’t it be cool if Damon showed up as Tom Hiddleston’s evil twin in the next Avengers? Damon’s character in the Kevin Smith comedy Dogma is a fallen angel who, alongside fellow fallen angel Bartleby (BFF Ben Affleck), attempts to find a loophole in Catholic dogma that will send them both back to Heaven after being cast out by God. Loki and Bartleby were banished to Wisconsin because Loki got drunk and, prodded by Bartleby, quit his job as the Angel of Death.

    Dogma is a bizarre, ballsy, and deliciously perverse film that also acted as a kind of launching pad for Damon’s career. As Loki, Damon got to use his then underused comedic chops, which likely led to his landing more comedic roles like Greg Kinnear’s conjoined twin in Stuck on You, that memorable cameo in Eurotrip (“Scotty doesn’t know!”), and the starring role in Sarah Silverman’s viral video “I’m Fucking Matt Damon.”

    Damon’s Moment: The opening scene, in which Loki tests a nun’s faith with “The Walrus and the Carpenter” poem from Through the Looking-Glass. “That’s an indictment of organized religion,” he says, making a compelling case. The nun walks away a skeptic, and Loki says to Bartleby, with a hint of a smirk, “I just like to fuck with the clergy, man. I just love it. I love to keep those guys on their toes.” — L.P.


    05. LaBoeuf, True Grit (2010)


    In a movie filled with solid performances (not to mention the typical Coen Brothers brilliance), Damon stands out as the puffed-up and slightly bumbling Texas Ranger LaBoeuf. True Grit is perhaps the most straightforward genre movie the Coens have ever produced, so most of its eccentricities originate in its characters, who differ substantially from those in the 1969 original. Damon is obviously a more accomplished actor than predecessor Glen Campbell, and he strikes the perfect balance between diving into the role of LaBoeuf and just having a ton of fun with it.

    In fact, long stretches of True Grit play as a kind of pissing contest between the two leads, Damon and Jeff Bridges — not the least of which is an actual shooting contest. As U.S. Marshal Reuben J. “Rooster” Cogburn, Bridges hams it up for laughs in the loudest ways possible. Damon takes a slightly subtler approach, but it’s clear that he’s pulling out all the stops in his supporting role (just listen to that pitch-perfect Texan accent, woo-wee).

    Damon’s Moment: Don’t blink, or you’ll risk missing out on Damon’s finest (and funniest) moment in True Grit. When 14-year-old farm girl Mattie Ross (Hailee Steinfeld) meets LaBoeuf for the first time, she sits up in bed and skeptically asks him, “Are you some kind of law?” LaBoeuf gives a slight smirk, leans back in his rocking chair, and smugly pulls his coat back to reveal a badge. “That’s right. I’m a Texas Ranger.”


    Everything about the delivery — his feigned nonchalance, the way he turns his head slightly to the side while showing his badge — is hilariously spot-on. What’s most impressive, perhaps, is that Damon didn’t stop once he got the Texan accent down; this scene alone proves that he was also an astute student of Lone Star mannerisms. — C.B.

    04. Jason Bourne, The Bourne Series (2002-2016)

    damon bourne

    Few would have expected that the skinny cipher in The Talented Mr. Ripley or even the nerdy Linus in Ocean’s Eleven would soon become the James Bond of his generation, but here we are. Jason Bourne (JB, no coincidence there) is intriguing on the page, but could have easily failed on the screen had it not been for the tight direction of Doug Liman (and later, Paul Greengrass), the shrewd writing of Tony Gilroy, and Damon’s earnest and magnetic performance as the anchor.

    Bourne’s quandary is selective amnesia — he retains the ability to speak several languages and knock enemies out cold with advanced combat skills, and yet he has no idea who he is or where he came from. In the first film, 2002’s The Bourne Identity, Damon is a man found floating unconscious in the Mediterranean Sea by benevolent fishermen, his back riddled with gunshots. Eventually, he takes an American passport name, Jason Bourne, and attempts to piece together his past, present, and future as part of some kind of government conspiracy while also evading assassins.

    The journey to unravel his identity and the larger purpose behind him propels Damon’s Bourne through three sequels, 2004’s The Bourne Supremacy, 2007’s The Bourne Ultimatum, and 2016’s Jason Bourne, and also through millions of box office dollars from moviegoers white-knuckling their armrests at every twist and turn in hopes that the good guy, who is often just as confused as they are, comes out on top.


    Damon’s Moment: Tough call, but this writer is going with — big spoiler alert — Marie’s death in The Bourne Supremacy. Sure, all of the shaky-cam, sped-up fight scenes are great, and the “She’s standing right next to you” scene is spine-chilling every time. But it’s Bourne’s devastatingly human moments, like kissing Marie goodbye and letting her go into the emerald green water that cut through the ruthlessness to the heart of a man worth rooting for. — L.P.

    03. Colin Sullivan, The Departed (2006)


    Damon seems to have the most fun when he’s allowed to go full Boston, and Colin Sullivan is about as Bahston as it gets. A more or less direct character foil to Leonardo DiCaprio’s Billy Costigan, Sullivan drifts between the roles of protagonist and antagonist without ever fully inhabiting one or the other.

    All the same, it’s rare for Damon to play the bad guy, and his undercover gangster is a welcome change of pace from the kinds of roles A-list actors are too often coaxed into. Speaking of A-listers, The Departed is filled with them, and through no fault of his own, Damon has a difficult time standing out in a crowd that includes DiCaprio, Jack Nicholson, and Mark Wahlberg in the profanity-laced performance of his career.


    Damon’s Moment: The Departed is a loud, aggressive, bombastic film, but Damon is rarely guilty of overacting. In fact, his best scene is probably his quietest. When Sullivan secretly meets Costello at an X-rated movie, the camera lingers on him as he squirms and tries to avert his eyes from the pornography. Sullivan is a pretty uncomfortable guy in general — and there’s definitely a subtext to his sexual impotence — but few scenes speak more loudly to his character than this one. — C.B.

    02. Tom Ripley, The Talented Mr. Ripley (1999)


    The Talented Mr. Ripley is a psychological thriller to the hilt: psychological in that our anti-hero, Tom Ripley, has a brilliant mind he uses to twist his victims into friendship, and thrilling even in the quietest of moments. Damon accomplishes something spectacular with Ripley: a manipulative liar, yes, but also a timid Lost Boy, a fragile figure upon whom first instinct is to cradle and protect. As Roger Ebert wrote in his 1999 review of the film, “He’s a monster, but we want him to get away with it.”

    Damon was nominated for a Golden Globe for his performance, and watching him carry the film with an almost blinding charisma, it’s easy to see why. In making himself a chameleon — his careful interplay between Jude Law, Gwyneth Paltrow, and especially Philip Seymour Hoffman revealing layers upon layers of smokescreen — Ripley’s believe-it-or-not is Damon’s tour de force.

    Damon’s Moment: Warning, major spoiler ahead! Still here? Ok, here it is: When Ripley kills his lover in the end. That one could flirt with the possibility of feeling sorry for Ripley, understanding that it had to be done, underscores the magnitude of Damon’s performance. His anguish, when he has no one to perform for but himself, is real. — L.P.


    01. Will Hunting, Good Will Hunting (1997)

    matt damon good will hunting

    Do you like apples? Well, Damon deserves all the apples for his Oscar-nominated turn as Will Hunting, a boy genius from South Boston who spends half his time getting in trouble and the other half solving advanced math equations. Damon co-wrote the script with childhood friend Ben Affleck, and he clearly relishes the chance to deliver extended, monologue-style takedowns to the people Will deems inferior (that is, pretty much everyone).

    But this isn’t Damon’s best work just because of a few great zingers. The young actor’s performance is one of stunning emotional depth, capable of inciting fits of laughter as well as tears. He spends 90 minutes shunning intimacy and building up defense mechanisms, so the moment he finally breaks down in the arms of his therapist is nothing short of cathartic. The distance he travels to get to that point is extreme, and it’s a testament to Damon’s empathy as an actor as well as a writer. Good Will Hunting is so character-driven that it might have worked just as well as a stage production, but it’s hard to picture a better fit for the lead role.

    Damon’s Moment: In terms of sheer fun, it’s hard to top that intellectual beatdown he delivers to Mr. Harvard Ponytail. Not only does it demonstrate Will’s fierce intelligence and loyalty to his friends, but the schadenfreude is simply off the charts. — C.B.