Matt Damon's Best Movies, Ranked
When he’s not busy doing cameos in the MCU or acting as Jimmy Kimmel’s arch-nemesis, Matt Damon is usually found being one of the most consistent leading men in Hollywood.
Comfortable in a wide range of genres and tones, he’s the kind of actor who rarely blows you away emotionally (his three unconverted acting nominations at the Oscars perhaps attest to that) but who also never gives anything below an 8/10 performance, regardless of the movie around him.
This year, Damon has had the responsibility of shouldering the biggest movie of the summer—and perhaps of his career. We are talking, of course, about Cristopher Nolan’s The Odyssey, in which Boston’s favourite son has graduated from supporting turns in the director's previous films (Interstellar and Oppenheimer) to finally take the lead role of Odysseus—the Greek hero whose attempts to get back home are forever being disrupted by various beasts, witches and gods—in what is arguably the starriest cast of the decade so far.
All of which got us thinking about the prolific actor’s best movies. In the list below, ranked in descending order, I’ve rounded up a selection that hopefully reflects the actor’s skills, charisma and his remarkable versatility. Read on for more about each one and use the guides to find them on all of the usual platforms.
The Amalfi Coast locations; the impossibly chic clothes; the immaculate performances by Jude Law and Gwyneth Paltrow; and a supporting turn by Philip Seymour Hoffman for the ages—indeed, there is no shortage of reasons to watch Anthony Minghella’s The Talented Mr Ripley. Matt Damon’s turn as Patricia Highsmith’s most slippery protagonist may be the best of the lot, though.
The character had already been played a couple of times before—by Alain Delon (Purple Noon) and Dennis Hopper (The American Friend)—but Damon brought a much different energy to the role for Minghella’s endlessly stylish classic. Set to be the director’s glorious return after sweeping the Oscars in 1998 (nine wins from 12 nominations) with The English Patient, Minghella delivered a film that felt defiantly spiky, uncomfortable, and notably queer (zero wins from five).
I love both movies very much, but there’s no doubt which one has better stood the test of time. It’s still the best thing Damon has starred in.
Another great string in Damon’s bow is his phenomenal career as an action star. We got to see a little bit of this in The Rip earlier this year and will no doubt get to see a bit more of it in The Odyssey, but Damon’s definitive action role will always be Jason Bourne.
Since first appearing as the lethal but forgetful asset in The Bourne Identity in 2002, Damon has gone on to play the character a further three times. For me, the second (Supremacy) and third (Ultimatum) installments (tellingly, they're the only ones both written by Tony Gilroy and directed by Paul Greengrass) remain the strongest in the franchise.
It’s strange given the amount of great movies he’s been in, but Damon hasn’t ever really threatened to take home an acting Oscar. He did win a Golden Globe for The Martian in 2016, even if it wasn’t really a comedy, but his only time on stage as a winner at the Oscars was when he and Ben Affleck (who were a sprightly 27 and 25 years old at the time) enjoyed a shock win for Best Original Screenplay.
The year was 1998, and the movie was Good Will Hunting, a cosy autumnal classic that I never get tired of watching. The story follows Damon’s unlikely mathematical genius as he gradually opens up to a shrink played by Robin Williams.
The late great comedian won Best Supporting Actor that year, but Damon (who was nominated as the lead) had to make do with the honour of sharing the same air as Peter Fonda, Dustin Hoffman, Robert Duvall and the eventual winner Jack Nicholson (for As Good as It Gets), who were all bona fide legends as well as 30-40 years his senior. I presume he didn’t mind.
If the Ocean’s movies confirmed Damon as the new kid on the A-List block, The Departed cemented his place in the big leagues. Here was a movie directed by Martin Scorsese with a cast featuring Leonardo DiCaprio, Jack Nicholson, Martin Sheen, Alec Baldwin and Mark Wahlberg, and yet depending on how you looked at it, Damon was playing the juiciest part.
Sure, DiCaprio’s good cop is the one we root for, but Damon’s rat narrates most of the movie and gets all the best lines and scenes. The movie, which follows the race between an undercover cop and a crooked policeman to find each other's identities first, is a remake of the modern Hong Kong classic, Infernal Affairs. It’s also Scorsese remaking GoodFellas by way of Massachusetts. It’s not the director’s best movie, I would argue, even though it won Best Picture, but it might be his most rewatchable.
Mileage will vary on where The Odyssey lands on most peoples' lists of top Damon movies at the point, so let's just say that we're "debuting" it just outside his finest work so far. This is not a reflection on the movie itself or its clear importance to Damon's career (he may yet win that acting Oscar), it's just always a good idea to let the dust settle a little before adding a movie to an actor's Mt. Rushmore.
What we can say is that Damon carries a great deal of Nolan's monumental epic on his finely sculpted back—including in a number of scenes that look like they were absolute hell to film. But he's really at his best in Odysseus' more vulnerable moments, like when he approaches Penelope as a beggar late on, or when he's tied to mast to hear the Sirens' song. The awards race will be long and rocky, but he's certainly in with a chance.
When Damon was breaking out in the 1990s, he quickly amassed a respectable C.V. of legendary collaborators. A year after Zwick came Francis Ford Coppola's The Rainmaker—a John Grisham courtroom drama adaptation that came very close to making this list—before the biggest of the biggies another year later: Steven Spielberg’s Saving Private Ryan.
Of all the “how do we get Matt Damon home?” movies to date (Martian, Interstellar and Odyssey all fall into this genre), Spielberg's WWII classic remains the most prestige-heavy project he's been involved in. Of course, in other circumstances, it would be much higher on this list, but seeing as Damon (who plays the title role) only really shows up in the latter (and frankly less interesting) bits of the movie, I’ve decided to keep it out of the actor’s top tier.
The easiest way to imagine Ridley Scott’s The Martian is to think of Cast Away in space. We get Damon as an interplanetary Robinson Crusoe, stranded on the unforgiving surface of Mars. Although, unlike Tom Hanks and his trusty volleyball in that Robert Zemeckis classic, Damon’s best friends are the good old laws of science.
The Martian was, of course, written by Andy Weir, the acclaimed author behind this year’s smash hit Project Hail Mary—and if you enjoyed the practical problem solving that makes up the majority of that film, you’re going to have a great time with this one, too.
It says all you need to know about Damon’s watchability that his most successful starring movie (in terms of box office) to date is mostly about a man trying to grow potatoes.
Goofy and charming Damon is probably the most underrated Damon we have. We got to see it in full midlife crisis mode in Alexander Payne’s occasionally brilliant Downsizing and in Steven Soderbergh’s The Informant!, in which Damon hid his leading-man good looks behind a modest moustache and a pair of aviator glasses.
That role, of course, was one of many goofy guys he’s played for Soderbergh over the years—a fruitful artistic collaboration that began with the still flawless Ocean’s Eleven 25 years ago. Clooney and Pitt naturally take up most of the oxygen in Soderbergh's jazzy heist classic, but Damon’s ability to go toe-to-toe with them was proof he was on his way to triple-A status in Hollywood. The sequels ain’t bad, either.
One of the earliest roles that allowed Damon to show his chops was the part of Specialist Ilario in Edward Zwick’s gripping Gulf War drama Courage Under Fire.
Released in 1996, just shy of Damon’s breakout year, it comes from a genre of American heroism that would later (along with the actor himself) be torn to pieces in movies like Team America: World Police, but don't let that get in the way of what is really a damn fine movie and genuinely the kind of thing that Hollywood doesn't make anymore.
The story centres on Denzel Washington’s Nat Serling, a Lieutenant Colonel who is tasked with determining whether a captain (Meg Ryan) who died during a tense operation should become the first woman to receive the Congressional Medal of Honour. Damon only appears in a few scenes as Ilario, a medic who survived the operation and is now dealing with the emotional trauma, but it allowed him to share the screen with Washington, and he more than holds his own.
We’re so used to seeing Damon as the hero that a performance like the one he gives in The Last Duel comes as a big surprise. He’s played various kinds of bad guys over the years, and in movies as disperate as Margaret and Interstallar, but it’s rare that you get to see him rolling around in the dirt like he does in The Last Duel—and I mean that in both the metaphorical and figurative way.
Ridley Scott’s last great movie (at time of writing) takes Akira Kurosawa’s Rashomon and plunks it in the French middle ages to tell an age old (and apparently true) story of j’accuse from the perspectives of a knight (Damon), his wife (Jodie Comer) and his former squire (Adam Driver)—at least that’s how I remember it.
