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A conjoined twin, a stranded astronaut, a bipolar informant, and a French knight — these are but a few of Damon’s diverse roles.
Matt Damon has been acting for over 30 years, but the 55-year-old star is only just getting started.
This summer, Damon leads Christopher Nolan’s acclaimed adaptation of Homer’s Odyssey, playing the hero Odysseus, the king of Ithaca. Speaking about getting the opportunity to be a middle-aged blockbuster lead, Damon told Time magazine, “There aren’t a lot of people in their mid-50s as protagonists in these epics. I looked at this like the last movie I’d ever do.”
Damon’s career took off with 1997’s Good Will Hunting, the screenplay of which he cowrote alongside his lifelong pal and costar, Ben Affleck. Since then, he has continued to work behind-the-scenes, teaming with Affleck and Nicole Holofcener on the script for Ridley Scott’s The Last Duel (2021) and producing Manchester by the Sea (2016) and this year’s The Rip.
But Damon is most acclaimed for his naturalistic approach to acting, often taking on roles in which he portrays a grounded and understated “everyman.” Still, he can go for broke — he’s got solid comedic chops, like in the role of Carol, the bumbling pilot, on 30 Rock, and he can do a disarming villain, like in The Talented Mr. Ripley (1999). He can also turn a brief cameo into an unforgettable piece of pop culture history.
Ahead, we celebrate — and rank — the 10 best roles of Matt Damon’s career so far.
01 of 10
Stuck on You (2003)
What would a list of the Best Matt Damon Performances be without the Farrelly brothers’ Stuck on You? The 2003 comedy stars Damon and Greg Kinnear as brothers Bob and Walt Tenor, who are literally attached at the hip. The Tenors are conjoined twins and hometown heroes, known as the best and fastest grillers on Martha’s Vineyard.
Walt has aspirations to be a big Hollywood actor, while his brother would much prefer to stay out of the spotlight. But when Walt’s local one-man show becomes a surprise success, he takes the two of them on a trip to Hollywood to follow his dreams of being a star. However, the brothers’ desires for differing lives threaten to tear them apart — for real.
Relying heavily on physical comedy, Stuck on You proves Damon’s underrated comedic prowess while still showcasing his strengths in being an emotionally grounded screen presence, even when the movie he’s in is patently absurd.
02 of 10
Oppenheimer (2023)
Damon’s role in Christopher Nolan’s Oppenheimer is at once ferocious and a bit funny: Gen. Leslie Groves, a U.S. Army officer who taps J. Robert Oppenheimer (Cillian Murphy) to lead the Manhattan Project. Gruff and determined, Groves also comes across as a bit removed from the complicated, world-ending science that he needs to understand.
Here, Damon is firmly within his grounded, everyman persona, as his Groves provides the perfect foil to Oppenheimer’s high-minded genius. Despite being a character with far less screen time than that of the Oscar-winning lead, Leslie Groves still leaves an unmistakable impression.
03 of 10
The Last Duel (2021)
Damon takes on the facade of an arrogant and unlikable character in his portrayal of French knight Jean de Carrouges. Based on real events, Ridley Scott’s film was penned by Damon, Affleck, and Nicole Holofcener to track three narratives in the story of the last trial by combat in France.
These three dueling (no pun intended) perspectives belong to Jean, Jacques le Gris (Adam Driver), and Marguerite de Carrouges (Jodie Comer). After years spent as both friends and enemies, Jean and Jacques end up in a fight to the death after Marquerite, Jean’s wife, accuses Jacques of raping her.
Though the film has often been overshadowed by its questionable accents and hairstyles, it is ultimately a skillful representation of how men literally see the world differently than women. And while Affleck does seem like he’s having the most fun as the indulgent Count Pierre d’Alençon, Damon nevertheless shines in his annoyingly honor-bound and self-centered de Carrouges: “Damon happily forfeits his likability for the sour, spluttering Jean,” wrote EW’s Leah Greenblatt.
04 of 10
The Departed (2006)
Massachusetts native Damon returned home for Martin Scorsese’s Irish-Americanized take on the Hong Kong flick Infernal Affairs. Damon stars as Colin Sullivan, a plant embedded within the Massachusetts State Police by mafia boss Frank Costello (Jack Nicholson). Meanwhile, the mob has a rat within their own ranks: undercover state trooper Billy Costigan (Leonardo DiCaprio). When both groups realize they have a spy among them, it becomes a deadly race to uncover the moles.
Here, Damon plays against type, a villain nestled within the false persona of a good guy — his typical bread and butter. However, Colin is deeply unlikable, a sleazy mole who is nevertheless magnetic. His performance is perfectly matched against DiCaprio’s Costigan, a contrast that only serves to make Damon’s work resonate harder.
05 of 10
True Grit (2010)
In the Coen brothers’ reimagining of Charles Portis’ 1968 novel — which was first adapted into a 1969 film starring John Wayne and Glen Campbell — Jeff Bridges stars as aging, alcoholic lawman Rooster Cogburn, who is hired by plucky teen Mattie Ross (Hailee Steinfeld) to help her get revenge on the man who murdered her father.
Accompanying this unlikely duo is Damon’s Texas Ranger LaBoeuf, who is seeking the same man, Tom Chaney (Josh Brolin), for the murder of a state senator. Together, the bickering trio sets forth into dangerous territory to track down Chaney and dispense their own type of justice.
It is in True Grit that Damon shows just how chameleonic he can be while still utilizing familiar traits. In EW’s review, Lisa Schwarzbaum wrote, “This isn’t the first time recently that I’ve delighted at how Damon has become one of Hollywood’s most enjoyable, versatile actors. I’m happy every time I see him, and he’s a great costar here, flavoring his LaBoeuf — pronounced La Beef, if you please — with a piquant seasoning of Ranger vanity, bounty-hunting avarice, and Dudley Do-Right earnestness.”
06 of 10
The Martian (2015)
Adapted from Andy Weir’s novel of the same name, The Martian centers on Damon’s Dr. Mark Watney, a botanist on a mission to Mars who becomes stranded after things go awry. Alone and with limited resources, Watney does his best to make the most of his unprecedented situation while his comrades on Earth plan to get him back home. Using ingenuity, humor, and resourcefulness, he fights to survive on the hostile planet.
Damon’s performance earned him an Academy Award nomination for Best Actor, and at the time many critics agreed that it was the best performance he had delivered in years. Indeed, Watney gives Damon the perfect mix of humor and heart, as the actor pivots skillfully between comedic and dramatic moments.
07 of 10
Good Will Hunting (1997)
Damon’s breakout role in Good Will Hunting had him taking on a boyish powder keg of repressed emotion. He stars as Bostonite Will Hunting, a janitor at MIT born on the wrong side of the tracks who finds himself facing prison time following a street fight. But after mathematics professor Gerald Lambeau (Stellan Skarsgård) discovers that Will is a self-taught genius, he lobbies to have Will avoid jail time if he studies math while attending therapy sessions.
Resistant at first, Will finds himself slowly opening up to his troubled but patient therapist, Sean Maguire (Robin Williams), who understands how to get through to the volatile young man. While Williams has been rightly praised for giving the performance of his career — and winning the Academy Award for Best Supporting Actor in the process — Damon is handily on par. The young actor deftly oscillates between vulnerability and rage in a difficult character who is constantly wrestling with his trauma.
Damon’s grounded performance plays off against Williams’ wit, grace, and humor effortlessly, and it proved that he could carry the weight of a complex lead performance.
08 of 10
The Odyssey (2026)
It’s very likely that you read Homer’s Odyssey in high school English class and don’t remember a thing about it, so here’s a quick recap: The plot centers on Odysseus, the king of Ithaca, who leaves his home to fight in the Trojan War for 10 years. However, his journey back is not just difficult — it takes him an additional 10 years. Along the way, Odysseus is faced with a series of trials that test his mental and emotional stamina, such as encountering the Cyclopes Polyphemus and the cunning witch Circe.
Reviews of Christopher Nolan’s newest film are overall stellar, and Damon in particular has received a fair bit of praise. His character shoulders the weight of the world on his shoulders, making him endlessly compelling. Odysseus isn’t some faultless champion: He is human, and Damon brilliantly plays him as such.
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09 of 10
The Informant! (2009)
The Informant! adapts the real-life story of Archer Daniels Midland whistleblower Mark Whitacre, who became an informant for the FBI over his company’s price-fixing tactics during the mid-1990s. However, a simple undercover job eventually spirals out of control, as Whitacre’s increasing mental instability and the coverup of his own crimes jeopardizes both his life and the entire operation.
Some critics were wary of the way the film seems to trivialize a very serious series of events with an ironic and satirical tone; at the time, EW wrote that “[Steven] Soderbergh ultimately made the choice to abandon interesting, dispassionate empathy for the more quick-fix payoff of amusement.”
However, we couldn’t knock Damon’s manic everyman performance, another role in which he takes his strengths and creates something entirely new. “Damon, fattened up to fit his boxy suits, wears Whitacre’s slack demeanor beautifully. The star — who has quietly and steadily turned into a great Everyman actor — is in nimble control as he reveals his character’s deep crazies.”
10 of 10
The Talented Mr. Ripley (1999)
Some might say that The Talented Mr. Ripley ran so that Saltburn could walk. Adapted from Patricia Highsmith’s novel of the same name, the film stars Damon as Tom Ripley, an American con artist who, while pretending to be a Princeton graduate, is hired by a man who believes Ripley went to school with his son, Dickie Greenleaf (Jude Law).
Ripley is given $1,000 and sent to Italy in order to persuade the man’s spoiled playboy son to come home, but instead, Ripley becomes increasingly obsessed with Dickie and his lifestyle— ultimately, to dangerous ends.
Damon astutely weaponizes his persona of “aw shucks” affability for the role of Tom Ripley, which EW once admitted might have been “a hard sell” to “audiences soothed by his amiable boyishness.”
In the end, however, critic Lisa Schwarzbaum admitted that Damon was a perfect fit: “The facade works surprisingly well when Damon holds that gleaming smile just a few seconds too long, his Eagle Scout eyes fixed just a blink more than the calm gaze of any non-murdering young man. And in that opacity we see horror.” It’s this disarming villainy, only just concealed by Damon’s apparent good nature, that makes The Talented Mr. Ripley a masterful tightrope walk and arguably his best performance.
Read the original article on Entertainment Weekly
