vulture lists

Every Matt Damon Movie Performance, Ranked

Moviegoers love to root for Matt Damon. Photo: Twentieth Century Fox/Warner Bros./DreamWorks

This article was originally published in 2019 and has been updated to include The Last Duel, Damon’s latest.

For someone who has lived his entire life in the public eye — he was playing the bad guy in School Ties while he was still at Harvard — Damon, unlike his famous buddy Ben Affleck, has done an excellent job at hiding in plain sight. “I’m a married man with kids and there’s no scandal about me,” he said in 2015. “I don’t think I’ve done anything to create any mystique around myself.” That everyman quality may be a mask — a mask that sometimes drops, such as in his infamous discussion with Effie Brown on Project Greenlight — but it has been an incredibly effective one. Damon’s right: There’s little mystique about him. Clearly, that’s just the way he has always wanted it.

Damon has shown a certain pragmatic efficiency in his choices of roles, valuing respected directors rather than taking huge risks on passion projects himself. He has been smart and prudent, trusting other people’s visions, picking solid, sturdy projects that he has faith will work, rather than throwing caution to the wind. As a result, he’s put together a very old-school career, limiting embarrassment, but stretching when the right part arises. And some of his most fun roles are cameos so small they don’t even qualify for this list: He remains one of the highlights of both Steven Soderbergh’s Che and Unsane. He knows what roles work and which ones don’t.

Thus, the lows on this list of Damon’s big-screen performances are not as low as you might find on, say, Affleck’s list. But the highs still show off his range, and his intelligence. He has put together a nearly three-decade career at this point. He has, all told, rarely stepped too far afield. There are no truly bad Damon performances: He’s too controlled for that. He’s the ultimate professional.

39. We Bought a Zoo (2011)

One of Cameron Crowe’s late-career disappointments — we remind you, as always, that this parody Twitter feed had more suspense and emotional resonance than the movie itself — strands Damon as a widower who learns how to love again through his daughter and Scarlett Johansson and, oh yes, that zoo. Damon had to be persuaded to make the movie by Crowe, but he would have been better off resisting: We Bought a Zoo is so desperate to make an emotional impact that it’s difficult not to run screaming out of the theater. Damon tries his best to ground the movie in real grief, but Crowe leaves him hanging in the wind. This movie gets a little more embarrassing every year.

38. Downsizing (2017)

As Damon has gotten older, the ground has shifted beneath him a little: The earnest young privileged white kid isn’t the default protagonist anymore in Hollywood, which both takes the wind out of some of his characters but also can add resonance and nuance, if handled correctly. That ground shifts far too violently in this Alexander Payne misfire, in which Damon, facing financial strife, shrinks himself to reduce his expenses and environmental footprint but must readjust after his wife (a disappointing Kristen Wiig) changes her mind at the last minute. Downsizing is wildly ambitious — you name a social ill of the late 2010s, Payne tries to tackle it — but having Damon remain at its center, even when more interesting characters float in the periphery around him, is a mistake. The film ends up dragging him down in its callowness.

Available to stream on Paramount+

37. Suburbicon (2017)

George Clooney, who is always a little shakier behind the camera than everyone generally wants to admit, grabbed an old Coen brothers script and tried to attach a civil-rights subplot to it and … well, the script probably should have just stayed in the drawer, honestly. Damon plays a morally compromised suburban dad in the 1950s who keeps getting himself in over his head in an insurance-fraud plot. The actor is appropriately pathetic and bloated, and it’s occasionally fun to see him get his William H. Macy on. But Suburbicon is so wandering and consistently misfiring that Damon never really gets to play anyone but a thesis.

Available to stream on Paramount+

36. Elysium (2013)

Neill Blomkamp’s much-anticipated follow-up to District 9 stars Damon as an ex-con who is accidentally dosed with radiation by a futuristic corporation and has only a few days to live. Desperate, he tries to smuggle himself into “Elysium,” the perfect world reserved for wealthy people while the rest of us struggle down in the salt mines. Blomkamp’s commentary on the class struggle is comically obvious and rather dopey, and the story keeps jumping all over the place. Amid some disjointed ultraviolence and Jodie Foster’s truly insane accent, Damon looks a little bewildered by all the madness surrounding him.

Available to stream on Starz

35. The Brothers Grimm (2005)

Terry Gilliam didn’t want Damon for the part of Will Grimm in his fantasy film; he wanted Johnny Depp, but the Weinsteins didn’t think Depp was famous enough. (This was right before Pirates of the Caribbean.) Depp would have been a better fit, though: Damon is a little too sturdy for Gilliam, at least as a leading man. He needs to be a little wobblier, a little loonier. His co-star, Heath Ledger, fares a little better, but only a little: This is not one of Gilliam’s stronger outings.

Available to stream on HBO Max

34. Green Zone (2010)

Off the overwhelming success of the Bourne movies, Damon and director Paul Greengrass made this political thriller about an army officer (Damon) in Iraq charged with finding weapons of mass destruction. It turns out — and you may have heard this — there weren’t any, and it dawns on him that the Government Hasn’t Been Truthful With the American People. Greengrass’s attempts to wrap a political statement up in Bourne clothing is awkward and jarring, and the movie is more preachy and hectoring than particularly enlightening. There were many, many movies like this around this time. Just watch No End in Sight instead.

Available to stream on Netflix

33. All the Pretty Horses (2000)

Billy Bob Thornton had wanted to bring Cormac McCarthy’s bestseller to the screen for years, and when he finally got the chance, he delivered a three-hour version to Harvey Weinstein. Weinstein grabbed the film away from him and chopped nearly a full hour out, turning an ambitious retelling of a pivot point in the American West into a dull, hazy love story of no particular importance. Damon has said this is one of the most disappointing experiences he’s ever had making movies — saying it “broke Thornton’s heart” — and while there’s not likely going to be a “release the Thornton cut!” movement anytime soon, the outlines of what this could have been are visible. Damon is too generic in this trimmed-down version, but you can see hints of the performance that was lost.

Available to stream on Starz

32. The Legend of Bagger Vance (2000)

There are many things to dislike about this noxious Robert Redford nostalgia film — how it wastes Charlize Theron, how it was the last film for Jack Lemmon, the grossness of the Magical Negro trope, and how Will Smith does his best to fight through it — but Damon isn’t necessarily one of them. He’s appropriately earnest and even a little self-mocking at times; he might be the only person involved with this movie dimly aware how poorly it might age in the new century. A good guess: This is the last Matt Damon role where he ever plays anyone with a name even remotely close to “Rannulph Junuh.”

31. The Monuments Men (2014)

George Clooney’s underwhelming World War II ensemble drama, about a ragtag group of soldiers assigned to rescue great works of art before the Nazis get their hands on them, cast Damon as a curator who teams up with a fellow curator (Cate Blanchett). A sorta-kinda love story develops between the two, but it’s so awkwardly executed that it never feels very convincing. Frankly, Damon just seems outclassed by his co-star — he doesn’t bring the wit or sophistication that she exudes as easy as breathing.

Available to stream on Tubi

30. The Adjustment Bureau (2011)

This Philip K. Dick adaptation features Damon as an ambitious young congressman who discovers that the entire world is being controlled by … well, by men in fedoras. It’s a little confusing, and while the film has some big ideas, it feels compromised and rushed: It’s an indie movie trapped inside a Hollywood thriller and is unable to get out. The movie is mostly known now for Barack Obama’s joke about it. After Damon had given an interview saying he was “disappointed” with aspects of Obama’s first term, Obama, at the White House Correspondents Dinner, joked, “I’ve even let down my key core constituency: movie stars. Just the other day, Matt Damon … said he was disappointed in my performance. Well, Matt, I just saw The Adjustment Bureau, so right back at you, buddy.”

Available to stream on Peacock

29. Hereafter (2010)

Clint Eastwood’s poorly received drama about mortality and tragedy benefits from Damon’s presence as George, a seemingly ordinary guy who can communicate with the dead. Once those around him find out, of course, they want to use him to speak to their deceased loved ones, and Damon has the right amount of hushed anguish for the role. (He has to sell such mawkish lines as, “It’s not a gift, Billy, it’s a curse.”) Hereafter is ultimately too touchy-feely for its own good — too awed by its modest musings on the mystery of being alive — and the film suggests Damon isn’t so great at playing characters with a mystical bent. He’s too good at being ordinary to pull off this fantastical conceit.

28. The Zero Theorem (2014)

Another Terry Gilliam joint, but Damon benefits from a smaller, weirder role than he got in The Brothers Grimm. This is Gilliam in Kafka in Space territory, and while this story of a lower-level employee (Christoph Waltz) of a massive corporation trying to figure out a math problem that might reveal if life has meaning is … muddled, Damon has a blast as “Management,” a small role that lets him show up and be incredibly strange. We’ll cede to the description of our Vulture colleague Matt Zoller Seitz: His “natty suits, owlish eyeglasses, gray hair, and dulcet voice make him seem like Peter Bogdanovich’s all-powerful kid brother.” That’s pretty much right! We’re not sure about the movie, but Damon sure seems to be enjoying himself.

Available to rent on Redbox

27. The Great Wall (2016)

Damon’s “Chinese ponytail movie” is neither goofy enough to be delightful nor stirring enough to be epic. Teaming up with Hero and House of Flying Daggers maestro Zhang Yimou, he plays a European mercenary who must join forces with Chinese soldiers to defeat aliens. Reread that last sentence and ask yourself: “Why isn’t The Great Wall the greatest movie ever made?” Part of the problem is Damon, who seems a bit lost amidst the CG and corny storytelling. He plays his character so seriously that it only makes everything around him seem sillier.

26. Promised Land (2012)

A topical film with interesting themes but disappointing execution, Promised Land starred co-writer Damon as Steve, a folksy salesman for a natural gas company trying to persuade the residents of a small-town community to let his bosses drill on their land. This is Damon at his slimiest: Steve turns on the charm, utterly unconcerned by the fact that he knows that fracking destroys these communities. There’s a coldness to his photogenic demeanor that’s awfully appealing. Eventually, though, Promised Land loses its nerve and the character blands out. But before then, this is a fun turn to the dark side for an actor who tends to prefer the light.

Available to stream on Starz

25. Stuck on You (2003)

Damon hasn’t done a lot of straight comedy, though he can be extremely funny when called upon to do it. (It’s a shame we can’t put his Carol from 30 Rock on this list. “I’m a doorman … to the sky.”) Too bad that this Farrelly brothers comedy about conjoined twins (Damon and Greg Kinnear) is not one of their more raucous offerings: Stuck on You is mostly sweet and goodhearted rather than uproarious. Damon is certainly game, though, and we can confidently say this is the only movie that will ever exist that features cameos from Meryl Streep, Ben Carson, and Tom Brady.

24. Invictus (2009)

Can a bad accent torpedo a performance? In the case of Damon and Invictus, yes. He plays Francois Pienaar, a world-class rugby player leading the South African team in the wake of apartheid’s end. Clint Eastwood’s drama is a different type of sports film, merging politics with on-the-field action. (Morgan Freeman portrayed Nelson Mandela, who believed that the rugby team’s victory in the 1995 World Cup was crucial to restoring the nation’s morale.) Damon tries his best, but you can tell he’s trying very hard to be South African the entire time. You never quite buy it.

23. Margaret (2011)

Kenneth Lonergan’s embattled post-9/11 drama starred Anna Paquin as Lisa, a Manhattan teen seemingly at war with the world. Damon plays one of her teachers, who begins to develop a relationship with her that may cross the line. The actor is friends with Lonergan and even helped him pull out of a depression by commissioning him to write what became Manchester by the Sea, but in Margaret, Damon is just part of the ensemble. He’s solid as a man becoming seduced by his pupil, although he’s nowhere close to the film’s highlight performances, which include Paquin and Succession’s J. Smith-Cameron.

Available to stream on The Criterion Channel

22. The Rainmaker (1997)

This adaptation of the John Grisham novel turned out to be the last Hollywood film Francis Ford Coppola ever made, and Damon got a number of looks just for being the lead in a Coppola film. (It’s sort of amazing that Coppola, Robert Altman, and Sydney Pollack all made Grisham films.) Damon is callow and young and earnest, which is exactly what the film calls for, but he’s smart enough to stay out of the way and let the vast cadre of character actors do the heavy lifting, from Danny DeVito to Jon Voight to Mickey Rourke to Dean Stockwell to even Roy Scheider. This is more boring than Damon usually is, but he does the job he’s asked to do.

Available to stream on Starz

21. Stillwater (2021)

The first images of Damon as the Oklahoma oil rigger desperate to free his imprisoned daughter in France were widely meme’d: There was something so artificial, so Hollywood that such a world-famous Bostonian pretty boy, Good Will Hunting himself, would so blatantly play, essentially, the Stereotypical Trump Voter. Damon’s performance has a little more heart than that — he does everything he can to put the shiniest, most human face on a guy who, in his own words, is a “real fuckup” — but that’s actually part of the problem: Damon, like the movie, is too eager to be liked. (Tellingly, when a character explicitly asks Damon’s Bill Baker if he voted for Trump — which is honestly the subtext of the whole film — both Bill and the movie dodge the question.) Damon gets the accent mostly right, and he wears the Cabela’s hat and the goatee convincingly, but you never truly buy him as anything other than a movie star. Matt Damon, at his best, can lose himself in an Everyman role, but here, there isn’t one second you aren’t acutely, painfully aware that that’s Matt Damon up there.

20. Courage Under Fire (1996)

This Edward Zwick drama was one of Damon’s first semi-big films, although it’s still a relatively small part. He plays Ilario, a military medic who served with Captain Karen Walden (Meg Ryan), a helicopter pilot who died in the line of duty. Courage Under Fire follows Nathaniel Serling (Denzel Washington), who’s determining whether Walden should be the first woman to receive the Medal of Honor, and his investigation will find him hearing differing accounts of the same events. Ilario is broken up about Walden’s death, but Damon doesn’t oversell the waterworks. Watching this movie now, it’s shocking how young and thin he looks — he’s just a kid — but already enormously appealing.

Available to stream on Starz

19. Dogma (1999)

Damon shines in Kevin Smith’s uneven comedy as Loki, an angel who’s been banished to Earth alongside his bud, Bartleby (Ben Affleck, of course). In Dogma, they plot to get back into heaven on a technicality — if they succeed, though, all of existence is doomed. Dogma requires zero heavy lifting on Damon’s part, and the actor enjoys being a very Kevin Smith-y wiseass: Naturally, he’s a talker with plenty of attitude. This post–Good Will Hunting role was the kind of thing Damon could do as a lark at this stage of his career — he wasn’t so concerned yet about being Matt Damon, Movie Star™ — so while it’s insubstantial, it also has its charms.

18. Syriana (2005)

Stephen Gaghan’s oil-business ensemble drama casts Damon as Bryan Woodman, an energy analyst who is working with Prince Nasir (Alexander Siddig) after the tragic death of Woodman’s son. Syriana is a movie of ambition and ideas — Gaghan won an Oscar for his screenplay for Traffic — which means that sometimes Woodman is little more than a symbol of Cocky American Attitude, delivering bullet-point speeches that represent specific perspectives on the Middle East’s tenuous hold on our energy future. But Damon delivers them with gusto, while making room to play a grieving father who hopes that money can help him forget what he’s lost.

17. Interstellar (2014)

An unwitting dry run for his role in The Martian, Christopher Nolan’s sci-fi drama finds Damon playing Dr. Mann, one of several humans who has traveled across the cosmos trying to find habitable planets. (Matthew McConaughey’s crew rescues him, only to discover that Mann has been hiding information from them.) Interstellar was during the height of Damon’s stardom — when the surprise of him turning up in this movie as a supporting character was indeed a surprise — and the actor gets a rare chance to be underhanded and cowardly. We don’t expect it out of Damon, who subverts his nice-guy persona with relish.

Available to stream on Paramount+

16. Rounders (1998)

As we said when we talked about this movie in the Edward Norton rankings, it’s “basically Citizen Kane for gambling addicts and … perfectly fine for everybody else.” Damon’s character is less interesting than Norton’s, but Damon still has a knack of playing somewhat morally compromised heroes whom the audience nevertheless identifies with and cheers for. We have no doubt that this movie is No. 1 on this list for regular listeners of Bill Simmons’s podcast.

Available to stream on HBO Max

15. School Ties (1992)

This was Damon’s first major role — he was just 21 years old when School Ties was filmed. (You can also spot him very briefly in Mystic Pizza.) It’s fascinating that he would never play a more openly villainous character — even the talented Mr. Ripley has some shading — than he would here as the anti-Semitic prep-schooler tormenting Brendan Fraser’s Jewish football player. It is to Damon’s credit that he is truly loathsome in the part, capturing a specific sort of Northeastern prep-boy shit-headed-ness that he would end up fighting against as he got older. There’s a lesser career direction where Damon becomes a Christopher McDonald type, a William Peterson, the ultimate asshole Wasp white guy. We’re glad he didn’t go that way, but this is proof he could have done it.

Available to stream on Paramount+

14. True Grit (2010)

In 2010, Damon said in an interview that there were only two movies he’d done where he wouldn’t change a thing: The Informant! and this Coen brothers adaptation of the Charles Portis novel, which had been turned into a John Wayne picture in the late 1960s. Granted, Damon was promoting True Grit when he made that claim, so take his comment with a grain of salt. Nonetheless, it’s deeply fun to watch him play LaBoeuf, a buffoon who’s awfully proud of himself. (Just the way he slyly informs Hailee Steinfeld’s Mattie that he’s a Texas Ranger, as if he’s pausing for the round of applause he assumes is forthcoming, is terrific.) Coen brothers movies are often populated with dolts, and Damon happily joins the ranks of the filmmakers’ puffed-up fools.

Available to stream on Cinemax

13. The Last Duel (2021)

Damon has portrayed understated heroism in Saving Private Ryan and The Martian. He’s played villains in The Departed and The Talented Mr. Ripley. But his performance in The Last Duel is something different. Jean de Carrouges is a knight with a chip on his shoulder, constantly believing that the world is out to slight him, furious that he’s not recognized for the fearless warrior he believes himself to be. Put simply, Jean is a fool, and Damon is delightful in the role, delivering a portrait of thwarted male pride that’s just about unparalleled in his career. (The closest comparison, funny enough, might be the posturing, wimpy Carol from 30 Rock, except with more chain mail.) Determined to get vengeance on Adam Driver’s Jacques Le Gris — who Jean’s wife Marguerite (Jodie Comer) accuses of raping her — Jean comes across as the sort of manly hero you normally see in a Ridley Scott period epic, except he’s just a putz.

In Theaters Now

12. Gerry (2002)

The first of Gus Van Sant’s “death trilogy,” Gerry stars Damon and Casey Affleck as two ordinary guys wandering around the desert, eventually getting lost. Damon hasn’t shown much interest in experimental cinema, but this is as close as he’s ever gotten, acquitting himself quite nicely in this heavily improvised study of masculinity and existential dread. Stripped of the usual narrative trappings — plot, character, motivation — there’s something deeply sad about Damon’s persona, revealing a desperation beneath the boyish charm we rarely get to see. Gerry is a fascinating outlier in his oeuvre and definitely worth seeking out.

Available to stream on Peacock

11. Contagion (2011)

Living through a deadly virus outbreak is frightening — but what about being, inexplicably, one of the few who seems to be immune? Damon’s character, Mitch, experiences both in Steven Soderbergh’s Contagion, a chilly look at a devastating epidemic told through multiple viewpoints. His storyline, however, is closer to the film’s emotional center: Mitch’s wife (Gwyneth Paltrow) succumbs to the disease, and he must mourn her and his son’s death. (Never mind that he has to process the fact that she was cheating on him.) As a grief-stricken father still trying to be the rock for his surviving daughter, Damon is quite touching, unsure why he managed to live but devastated by the dystopian world that’s been left in the virus’ wake.

10. Saving Private Ryan (1998)

Playing the private that Tom Hanks’s company has risked their lives to save, Damon has a small but crucial role in Steven Spielberg’s Oscar-winning film: He’s the character that the whole movie’s emotional weight will eventually rest on. And Damon handles it just right, giving us an ordinary soldier who didn’t ask for this special treatment and would rather fight alongside his countrymen than be shipped home. Damon milks his All-American earnestness in Saving Private Ryan, which is important when you’re portraying a character who has to represent the Greatest Generation in only a handful of scenes.

Available to stream on Paramount+

9. The Good Shepherd (2006)

Directed by Robert De Niro, The Good Shepherd stars Damon as a fictional FBI agent who ends up being a critical founder of what would become the Central Intelligence Agency. The film tracks the history of the agency and, quietly, becomes a meditation on what it means to keep secrets your entire life, and the toll it takes on you and your family. Damon is as buttoned-up and emotionless as he gets, but you can see the weight of his job start to bear on him, and it culminates in a moment that’s legitimately moving. This is a better movie than it was received as at the time; people might be surprised by just how good it is.

Available to stream on Starz

8. Ford v Ferrari (2019)

Damon has the less flashy role in James Mangold’s stirring sports movie — you’ll leave the theater saying everything in Christian Bale’s cheery Welsh-as-a-Brit singsong accent — but he also has the trickier one as Carroll, a former champion race-car driver now sidelined but trying to lead his Ford team to winning the 24 Hours of Le Mans race. It’s Damon who has to balance Ford v Ferrari’s themes of art vs. commerce, of perfection vs. commodification, and his performance sneaks up on you. By the end, you realize you weren’t watching a sports movie: You were watching an old-school male weepie. It’s Damon who makes that work.

7. The Ocean’s movies (2001, 2004, 2007)

Damon was already a star by the time he was in Ocean’s 11, but it is to his credit — and to his clear reverence for his older co-stars — that he happily cedes the best scenes and biggest moments to George Clooney and Brad Pitt. Everyone treats his Linus as a kid, and he plays along, the super genius savant who is as savvy as everyone else but still feels like he’s in training. Damon is light and funny but still fits into the overall vibe, just pleased to be fitting in. Plus, his dad was played by the late Bob Einstein, and we want a universe where Matt Damon and Albert Brooks are related.

Available to stream on HBO Max

6. Good Will Hunting (1997)

It’s possible to find this Oscar-winning drama cloying and contrived and yet still be moved by Damon’s performance in it. He, of course, is Will Hunting, a Bawwwston screwup who’s secretly a math genius — but first, he must make peace with his past. Good Will Hunting embraces cliché, but Damon believes in his character’s basic decency: Will is a guy who’s made mistakes but is, deep down, a good person. Damon’s inherent boyishness was perhaps never better used than here; no matter how abrasive Will gets, Damon lets you understand the inner pain that’s driving such behavior. Movies about Troubled Youths are commonplace, but Damon and Good Will Hunting located the humanity within the trope.

Available to stream on Starz

5. The Departed (2006)

Damon hasn’t played a lot of bad guys — he’s too wholesome to be typecast in the role — which is why it was so fun to see him be the heel in Martin Scorsese’s Oscar-winning crime thriller. He’s Colin, a cop working for the Boston mob, and what’s especially terrific about the performance is that it’s the Beantown flipside of his portrayal in Good Will Hunting: Will was a tough kid with a sweet center, while his Departed character is outwardly decent but rotten underneath. In this live-wire film, Damon seems juiced not just by the dangerous milieu but by his exceptional co-stars. As big of an A-lister as he is, Damon often does his best work as part of an ensemble. Alongside Jack Nicholson, Leonardo DiCaprio, Alec Baldwin, Vera Farmiga, Martin Sheen, and Mark Wahlberg, he thrives.

Available to stream on HBO Max

4. The Bourne movies (2002, 2004, 2007, 2016)

In the Affleck-Damon friendship, Matt always seemed like the kid brother, even though Damon is a couple years older. Post–Good Will Hunting, Affleck had the starrier career. It wasn’t until 2002’s The Bourne Identity that Damon found his franchise — and proof that he could be an action hero. The actor’s unassuming demeanor was crucial to playing Jason Bourne, a guy who wakes up in the middle of the ocean with no idea of who he is or how he got there. Damon’s an inherently sympathetic figure, and so the reveal that Bourne is actually a ruthlessly efficient assassin turned out to be a shock. The Bourne Supremacy and The Bourne Ultimatum were superior sequels, with Damon capitalizing on the character’s no-nonsense smarts and physical prowess. For a short period, the Bourne films were the best movie series going. By 2016’s Jason Bourne, it was clear the old thrill wasn’t there anymore.

3. The Martian (2015)

In many ways, The Martian’s Mark Watney is the embodiment of what makes Matt Damon a movie star. He’s smart, savvy, a little shifty, but also handsome, earnest, and determined: He’s a guy you can’t help but root for. The Martian already feels outdated, with its celebrations of American ingenuity and cooperation — not to mention its foundational faith in science — to the point that four years later it almost feels like a period piece. But if you let it, The Martian can make you want to believe. It’s the sort of movie-star performance you’d expect from a Tom Hanks. That Damon showed that he had this arrow in his quiver is actually one of the most impressive things he’s done in his career.

2. The Informant! (2009)

“He is both the protagonist and the antagonist of this movie,” Damon once said of Mark Whitacre, the whistle-blower he played in Steven Soderbergh’s biting dark comedy. “All the situations he finds himself in are of his own creation and yet he has a really good heart.” On its face, The Informant! could be a new twist on The Insider, showing how Whitacre helped expose dubious practices inside his company, Archer Daniels Midland. Instead, it’s a film about the ultimate unreliable narrator — a man with bipolar disorder who can’t get out of his own way. Damon taps into a smiling nervousness he’s never revealed before, and the character’s digression-laden voiceover narration is a labyrinth which neither Whitacre nor the audience can ever escape. Because of The Informant!’s jaunty surface, it takes a while for us to realize how deeply sad this film is. Damon makes Whitacre’s inner torment heartbreaking, while also understanding how the character’s self-inflated image of himself can be bitterly hilarious.

1. The Talented Mr. Ripley (1999)

The longer that Matt Damon’s career stretches, the more it resembles that of other eternal nice-guy movie stars; like Jimmy Stewart, when he gets gritty, he can be fascinating. In 2019, plenty of culture critics have been memorializing the greatness of Movie Year 1999, but there hasn’t been much mention of Anthony Minghella’s fabulous Patricia Highsmith adaptation, about a young conman, Tom Ripley, who falls in with playboy Dickie (Jude Law) and his beautiful bride-to-be, Marge (Gwyneth Paltrow). “We wanted Ripley’s humanity to come across,” Damon once said. “In the book he’s this awful, calculating person, but Anthony and I tried to have him not ever manipulate anybody and come from a position of pure honesty all the time. He believes what’s happening and he believes the world he’s indulging in.” That’s all well and good, but the fact remains that The Talented Mr. Ripley is the study of a psychopath — an examination of someone who so desperately wants to be somebody else. Damon finds a gear he’s never really tried since, and Ripley’s unsettling longing makes him both tragic and frightening. As an actor, Damon is often clean-cut, but here he flirts with a darker, even kinkier side to his easygoing persona. Damon provides the character with his humanity, sure, but also what’s so sinister about the man. Twenty years later, the performance is still a shock.

Available to stream on Tubi

Grierson & Leitch write about the movies regularly and host a podcast on film. Follow them on Twitter or visit their site.

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Every Matt Damon Movie Performance, Ranked