Is Matt Damon a bona fide A-list movie star or merely a very successful character actor? The answer, of course, is both. Which, in a way, makes him a rare kind of celluloid unicorn. It wasn’t always this way. In the early ’90s, Damon was a Harvard dropout hustling to get his big break on the big screen until enough rejections piled up that he was forced to create his own luck. With his runs-on-Dunkin’ Beantown buddy Ben Affleck, Damon cowrote and costarred in 1996’s blue-collar male-weepie Good Will Hunting. And just like that, he was off to the races armed with a Best Screenplay Oscar and the sort of chameleonic range few would have suspected.
Since then, the now 55-year-old has appeared in more than four dozen films—a smart and seemingly uncalculated crazy quilt of leading-man action blockbusters (the Bourne movies), stylishly giddy ensemble bro-fests (the Ocean’s trilogy), without-a-net one-man showcases (The Martian), hard-hitting historical pictures (Saving Private Ryan), and inspirational dramas (Air). Damon’s longevity seems to be a result of choosing films based less on how many lines or “for your consideration” close-ups he has and more on working with top-caliber directors and listening to his gut. It has served him well.
There are plenty of actors on Damon’s lofty rung in the Tinseltown hierarchy who choose projects based on the size of the payday attached to them (see Affleck’s CV circa 1998–2004). But thanks to his range and intelligence, Damon has always seemed to put the work first. That not only makes him a Hollywood rarity but also a capital-A Artist as well. With his latest movie now in theaters, Christopher Nolan’s epic adaptation of The Odyssey, it seemed as good a time as any to rank the quintessential professional’s top 25 performances. So on to the rankings … Head here for the full list, and read on below for a preview of our top five.
5. The Bourne Movies (2002–2016)
It’s tempting to say that we never knew how good we had it with Damon as Jason Bourne until Jeremy Renner’s wet firecracker, The Bourne Legacy. But the truth is we all knew how great Damon was as Robert Ludlum’s amnesiac, bare-knuckle-brawling spy from the jump. For the first stage of his career, Damon was pegged as the thinking man’s hero. But the Bourne movies showed that he could be cerebral while also scraping up his fists, getting into car chases, and beating the shit out of black-ops goons with nothing more than a rolled-up magazine. It’s no wonder that in the wake of Bourne’s reinvention of the action genre, every subsequent cinematic punch ’em up would ape his hero’s style. Even 007 would take a page from the Bourne playbook by casting Daniel Craig as a more brutish and brutal Bond.
4. The Odyssey (2026)
Christopher Nolan took on an impossible challenge when he first announced his adaptation of The Odyssey. It’s a nearly impossible feat—one which Nolan pulled off spectacularly—but it’s Damon’s Odysseus who shoulders most of the film’s burden. He’s in just about every shot of the nearly three-hour production. So it was on Damon as much as it was Nolan to answer the larger question of why 2026 felt like the right year to adapt The Odyssey. Well, the actor’s take on the ancient Greek hero as a soldier who is broken from his horrific experiences at war answered that question right away. Damon’s Odysseus acts like he’s seeing out the end of civilization itself, even as he fights to keep living in it. While a more imposing actor may have played up Odysseus as a macho military genius, Damon’s measured character was the right match for Nolan’s vision.
3. Good Will Hunting (1997)
It’s too obvious to say that this is where Damon’s career begins in earnest. But it also happens to be true. The story that wound up onscreen is undeniably personal and great and literate and heartfelt and moving thanks to both Damon’s screenplay and his performance. But the Horatio Alger tale behind the making of the movie is, in its own way, just as impressive: A struggling wannabe actor knuckles down and writes his own ticket out of obscurity and winds up onstage at the Academy Awards to receive an Oscar statuette with his best friend. It’s almost too far-fetched to be believed. Yet in its unlikely way, it’s the most rousing character arc that Damon’s ever created. How you like them apples?
2. The Talented Mr. Ripley (1999)
Anyone who’d been a fan of Patricia Highsmith’s sinister series of Ripley novels had to be a bit disappointed by the casting of Damon as the murderous serial impostor, Tom Ripley. He seemed too vanilla, too aw-shucks to get at the con man’s countless layers of evil. But Damon silenced the naysayers with his nuanced turn as the outsider pressing his nose against the glass window of privilege embodied by Jude Law’s Dickie Greenleaf and his impossibly beautiful and poised fiancée played by Gwyneth Paltrow. Anthony Minghella’s film treads a tad too lightly on the story’s gay subtext, but Damon (even in snug, bright-yellow swim trunks) makes you feel the aching longing and envy he experiences in Dickie’s rarefied presence. Two decades ago, this was the kind of role that could hurt an actor’s career, but Damon digs deep and dives into the darkened deep end headfirst.
… and for our number-one pick?
