Matt Damon’s 15 Best Movies, Ranked

Matt Damon’s 15 Best Movies, Ranked

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 drop-out 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 co-wrote and co-starred 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 50-year-old has appeared in more than four dozen films—a smart and seemingly uncalculated crazyquilt of leading man action blockbusters (the Bourne movies), stylishly giddy ensemble brofests (the Oceans trilogy), without-a-net one-man showcases (The Martian), hard-hitting historical dramas (Saving Private Ryan), and even experimental out-there indies (Gerry). Damon’s longevity seems to be a result of choosing films less on how many lines or “for your consideration” close-ups he has, but more on working with top-caliber directors and listening to his gut. It has served him well. (It didn’t hurt that, up until 2021 anyway, he also operated largely without controversy. That has certainly changed as of late.)

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 C.V. 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, the desperate-father drama Stillwater, it seemed as good a time as any to rank the quintessential professional’s Top 15 Performances. So on to the rankings…in descending order of greatness.

15. Gerry (2002)

Gus Van Sant’s existential ramble is like nothing else on Damon’s resume. Which is part of what makes it so fascinating. Reuniting with the Good Will Hunting director, Damon costars with Casey Affleck as a pair of ordinary guys who call each other “Gerry” as they wander around in the desert and get lost. Depending on your cinematic constitution, Van Sant’s avant-garde slice of improvisational aimlessness is either intriguingly confounding or unmitigated torture. But it’s proof that Damon isn’t afraid to occasionally step out on the ledge and leap headfirst.

14. School Ties (1992)

Made around the time that Damon was bidding adieu to Harvard Yard, School Ties was the young actor’s first consequential movie role. And two of the things that make it more than just a footnote is that a.) it’s a surprisingly effective coming-of-age tale and b.) he actually gets to play the film’s villain—something he would rarely do in the years to come. As an anti-Semitic prep school jerk who torments Brendan Fraser’s Jewish football player hero, the baby-faced Damon oozes toxic WASP-privilege prickdom. The actor’s feat is that, if you squint just a little, you can see the insecurity beneath all of his bile.

13. Contagion (2011)

One of the through-lines in Damon’s career is that if he really connects with a filmmaker he’ll re-team with them over and over again. See Gus Van Sant. Or Paul Greengrass. Or Steven Soderbergh, the director of the Oceans movies, whose white-knuckle thriller Contagion now feels like a prescient Nostradamian howl about a global virus pandemic. But even before COVID-19 would turn the movie into a prophecy fulfilled rather than a far-fetched nightmare, this was a harrowing movie to not only sit through but also to reckon with. The story ricochets between multiple viewpoints, but Damon soars in one of the trickiest roles—the inexplicably immune survivor mourning the deaths of his wife and son. He makes you feel that sometimes it’s the person whose left behind who gets the shorter end of fate’s stick.

12. Rounders (1998)

Thanks to a confluence of two very different late ‘90s pop-culture events—Damon’s post-Good Will Hunting vault to Tinseltown’s A-list and the simultaneous rise of Texas Hold ‘Em as a late-night ESPN spectator sport—Hollywood was ready to gamble on this poker-themed buddy film. It’s like a more predictable and upbeat version of Robert Altman’s California Split only with the Elliott Gould and George Segal parts played by Damon and Ed Norton. Norton gets the flashier part as the weaselly compulsive loose cannon, but Damon acts like an anchor, preventing the film’s more ridiculous moments (basically any scene involving John Malkovich’s borscht-accented Teddy KGB) from drifting too far into choppy seas.

11. True Grit (2010)

No one ever has ever gone wrong by appearing in a Coen brothers movie. And to be honest, it was really only a matter of time before the fraternal filmmakers rustled Damon into their venerable stable of actors. In this adaptation of Charles Portis’ Western novel (previously made into a 1969 John Wayne oater) of the same name, Jeff Bridges and Hailee Steinfeld win the flashy-part jackpot, but Damon is note-perfect as the pompous Texas Ranger, LaBoeuf. He’s a classic Coen brothers type: the blowhard boob. And watching him get put in his place by a precocious 14-year-old girl is just one of this film’s many small pleasures. His totally sweet mustache is the icing on the cake.

10. Saving Private Ryan (1998)

When the pre-release buzz on Good Will Hunting started spreading through Hollywood like wildfire, Damon suddenly found himself in a bizarre position: overnight he’d become the industry’s latest It Boy. Big-name directors started wooing him hard. First, there was Francis Ford Coppola with The Rainmaker. Then came Steven Spielberg with this WWII masterpiece. Yes, Damon is the Private Ryan of the title, but he remains off-screen as more of an idea than a character until the closing minutes of the movie. In other words, there’s not a lot of actually heavy lifting here for the actor, but the movie lives or dies based on the few moments he has. Fortunately, he aces them in a way that a better-known actor would not have been able to. He’s the blank screen the entire mission is projected onto.

9. Ford v Ferrari (2019)

On paper, Ford v Ferrari sounds like the ultimate Dad Movie. On screen, well, it’s also the ultimate Dad Movie. But just because a movie happens to be a straight-down-the-middle, slightly square bit of old-school Hollywood filmmaking doesn’t mean that it can’t also be fantastic. And despite whatever you’ve heard, Ford v Ferrari is fantastic. Damon and Christian Bale make a perfect pair as real-life race car legends Carroll Shelby and Ken Miles, who put their grease-monkey smarts together to help the conservative Ford motor company beat the legendary Italian F1 powerhouse at their own game. The two stars each give master classes in this rousing underdog tale, albeit very different ones—Damon is Ego; Bale is Id—but neither would work without the other.

8. The Oceans trilogy (2001-2007)

When people say ‘they don’t make them like they used to,’ these are the kinds of movies they’re talking about. To be honest, I could take or leave Ocean’s 12, but the bookends in the Steven Soderbergh-directed series are exquisitely engineered heist films. They’re like byzantine Rube Goldberg contraptions, but instead of ping pong balls, rubber bands, and dixie cups, there’s George Clooney, Brad Pitt, and Matt Damon. Clooney is aces as the ringleader and Pitt is wonderfully daffy as his constantly snacking right-hand man, but the beauty of these films (besides the twisty mechanics of the capers) is that every supporting character on the team gets not their chance to solo, they also are given three-dimensional characters. As the resident pickpocket, Damon is 24-karat deadpan gold. There’s not a single line in this trilogy he can’t undersell…and make sing.

7. The Informant! (2009)

Another Soderbergh. Hey, if you happen upon a good thing, don’t throw it away, right? There are folks who love this dark comedy. I’m not one of them…but I’m not not one of them. Still, the reason it ranks so high on this list is because Damon is absolutely mesmerizing in it. As a corporate whistleblower, Damon should be the hero. And he would be in any other film. But Soderbergh turns The Informant! into a tricky, high-wire balancing act with Damon teetering as its unreliable narrator. Are we rooting for this character or not? That’s a challenging assignment for any actor, but Damon keeps the audience off balance until the end credits. It’s not his showiest performance, but it’s arguably his most complex.

6. Courage Under Fire (1996)

This is the sort of decent-but-formulaic middlebrow film that director Edward Zwick seems to excel at. Still, it features the first truly indelible moment in Damon’s movie career. Yes, School Ties came before it. But his gaunt, ghostly presence is unshakeable here. Denzel Washington stars a military officer trying to determine whether a dead helicopter pilot (played by Meg Ryan in flashbacks) deserves to be the first woman to receive the Medal of Honor. Damon plays one of her fellow soldiers, a medic, who Washington interviews to get the truth. With tears brimming his eyes, Damon is thin as a wraith, depressed and suffering from PTSD. He’s seems so fragile and frail, he’s almost unrecognizable. Even after Washington moves on to interview the next soldier on his list, it’s Damon who you can’t stop thinking about. In just a few short minutes of screen time, his impact is so harrowing it haunts the rest of the movie.

5. The Departed (2006)

Yes, we all know that this is not the movie that Martin Scorsese should have won the Oscar for. But let’s move on because The Departed is a damn good film. While no one knows the mean streets of New York better than Scorsese, this Boston-set cat-and-mouse crime flick takes place on Damon’s home turf. So maybe it’s not surprising that he’s the best thing in it. A loose remake of the Hong Kong classic Infernal Affairs, The Departed is like a chess match being played on two boards simultaneously. Leonardo DiCaprio is the cop who manages to go undercover with Jack Nicholson’s mob kingpin and Damon is his reverse—the mobster who infiltrates the cops. What sounds overly schematic on paper works like gangbusters on screen thanks to the two leads. In a rare baddie turn, Damon isn’t just the only actor in the movie who nails the accent, he shows that he’s capable of playing a character whose rotten to the core.

4. 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, bareknuckle-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.

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 on screen 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 on the stage at the Academy Awards to receive an Oscar statuette with his best friend. It’s almost too farfetched to be believed. Yet, 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 imposter, 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 fiancé 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 head-first.

1. The Martian (2015)

It’s hard to imagine a role more bespoke to Damon’s off-screen persona—or at least his perceived off-screen persona—than that of Mark Watney, the hero of Ridley Scott’s The Martian. He’s brainiac smart, charmingly funny, and resourcefully can-do. He also happens to be stranded on the Red Planet all alone. Like Tom Hanks in Castaway or the three seemingly doomed astronauts in Apollo 13, Damon’s Watney makes science and hi-IQ problem solving not only cool, but nerve-wracking and tense. His life depends on his wits. Still, what makes The Martian more than just a big ol’ four-quadrant Hollywood blockbuster is that it’s also a stealthy acting tour de force. Damon has to carry virtually the entire film on his back, which of course is the kind of thing that every actor dreams of until they have to actually do it. Watching it, you find yourself rooting for Watney, but for Damon too. Because you’re never quite sure if he can pull this this one-man show off. Well, he can…and he does. Even if you had a choice, you wouldn’t be able to take your eyes off of him and him alone.

Chris Nashawaty is a writer, editor, critic, and author of books about Roger Corman & Caddyshack. 

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