There are no truly bad Matt Damon performances on this list
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 Stillwater, Damon’s latest.
38. We Bought a Zoo 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.
34. The Brothers Grimm 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. 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.
30. The Monuments Men 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 . A sorta-kinda love story develops between the two, but it’s so awkwardly executed that it never feels very convincing.
26. The Great Wall 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.
22. Margaret 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.
18. Dogma Damon shines in Kevin Smith’s uneven comedy as Loki, an angel who’s been banished to Earth alongside his bud, Bartleby . 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.
14. School Ties This was Damon’s first major role — he was just 21 years old when School Ties was filmed. 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.
10. Saving Private Ryan 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.
6. Good Will Hunting 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.
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