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Every movie featuring Matt Damon and Ben Affleck, ranked
Of Damon and Affleck's 14 films together, here are the ones you should watch and which ones to skip.
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After the runaway success of “Good Will Hunting,” Ben Affleck and Matt Damon became an inseparable duo in the public eye. Almost 30 years later, the childhood friends regularly return to their double act: They run a production company together, make late-night appearances listing every town in Massachusetts together, and even star in movies together – including their newest Netflix movie, “The Rip.” (Read my review.)
That wasn’t always the case, however. After Damon and Affleck established themselves as stars, they went 15 years without appearing in a film together.
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Despite that lengthy gap, Matt Damon and Ben Affleck have appeared in a total of 14 films together – though the number is only that high thanks to their friendship with director Kevin Smith, who keeps giving them small roles in his “View Askewniverse” movies.
With “The Rip” now out on Netflix, it felt like a good time to look back at the entire Damon-Affleck canon.
PS: This list is a little long, so we’re skipping Play or Skip this week. Think of 10-12 as the Skips and 1-5 as the Plays. And if that’s not enough, here’s a few recent streaming recommendations, as well as the full list of new titles coming to streaming in January.
Every Damon-Affleck movie, ranked
Not ranked. “The Good Mother” (1988) and “Field of Dreams” (1989): Damon and Affleck are on screen for less than a second in the 1988 Leonard Nimoy-directed drama and not at all in the 1989 Kevin Costner baseball drama. Despite merely standing in the crowd at Fenway Park, the college-aged pals left an impression on Costner: “They would both lean in at the same time, lean back at the same time, look at each other at the same time. We talked and they had this big enthusiasm. They were on fire.” (Available to rent)
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12. “The Third Wheel” (2002): Affleck and Damon’s first executive producer credits came on this forgotten romcom that made a little over $44,000. Affleck plays Luke Wilson’s bonehead coworker, while Damon has a one-scene cameo as a jealous ex of Denise Richards’ character. (Available to rent)
11. “Glory Daze” (1996): A Gen-X slacker film whose plot almost identically mirrors the superior “Kicking and Screaming,” Affleck is the angsty lead of a group of recent grads (including Sam Rockwell and French Stewart) who decide to stay in their dumpy college house instead of joining the real world. In another cameo, Damon plays a nonverbal drunk named “Pudwhacker”. Great time capsule of a soundtrack, terrible writing and ending. (Available to rent)
10. “Jay and Silent Bob Reboot” (2019): If you’re a diehard Kevin Smith fan, you probably enjoyed this return to the View Askewniverse, which features Damon and Affleck reprising their roles as Loki (from “Dogma”) and Holden (from “Chasing Amy”), respectively. Unfortunately, I am not. (Available to rent)
9. “Jersey Girl” (2004): This dramedy starring Affleck and Liv Tyler got a worse rap than it deserved upon release, earning 3 Razzie nominations mostly because of the public’s annoyance with wall-to-wall coverage of “Bennifer.” (Jennifer Lopez plays Affleck’s wife, who dies in childbirth early in the film). There are funny scenes (and yet another Damon cameo), but it’s not a great movie by any means. (Hoopla)
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8. “Jay and Silent Bob Strike Back” (2001): Smith’s showbiz satire features the titular pair (played by Jason Mewes and Smith himself) trying to stop Miramax from making a movie based on their comic book alter-egos. Affleck plays several characters in this one, and famously appears alongside Damon as they film a scene for the fictional cash-grab sequel “Good Will Hunting 2: Hunting Season”. (MGM+)
7. “The Rip” (2026): Joe Carnahan’s film is a bit too talky and stagnant at points, but it’s an enjoyable enough watch (read my full review), thanks in particular to Damon playing an inscrutable Miami narcotics cop who has led his team to a stash house to recover a “rip.” Affleck, playing a hotheaded subordinate (and longtime friend), rises to the occasion when needed. (Netflix)
6. “School Ties” (1992): People of a certain age wax poetic about seeing young Damon and Affleck (and Brendan Fraser, Cole Hauser, and Chris O’Donnell) in this prep school drama filmed in Concord, and you can see why. Though the film is heavy-handed in its anti-bullying message and treatment of Jewishness as target of mockery, the young actors acquit themselves well. (Hoopla)
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5. “Dogma” (1999): As a Wisconsin native, I don’t love that archangels (Affleck and Damon) banished from Heaven are sent to the Dairy State as punishment. But this religious spoof, starring Linda Fiorentino as an abortion clinic counselor who has to stop them from destroying the universe, is a big swing by Smith that mostly hits. Your mileage may vary on the third act, though. (Available to rent)
4. “Air” (2023): I stand by my original review of this Nike biopic: The movie’s strength is the joy we get from watching Affleck (as Phil Knight) and Damon (as Sonny Vaccaro) bust each other’s chops. Jason Bateman and Chris Messina get in a few good licks as well. (Prime Video)
3. “The Last Duel” (2021): A movie that has grown in my estimation since I initially reviewed it, “The Last Duel” is a medieval triptych of opposing perspectives, in which a knight (Damon) challenges his former friend (Adam Driver) to a duel after his wife (Jodie Comer) accuses the latter of rape. Damon is a standout, vacillating between chivalrous hero and impulsive clod depending on whose viewpoint we are seeing, while Affleck scores comic relief points as the hard-partying, bowl-cutted lord the two men serve. (Hulu)
2. “Chasing Amy” (1997): A film that inspired both raves and criticism for its depiction of sexual fluidity back in 1997, “Chasing Amy” was a shock to the romcom system upon release, depicting a straight comic book artist (Affleck) in love with a lesbian comic book artist (Joey Lauren Adams) and the schism this causes with his creative partner (Jason Lee), who may or may not be in love with him. Damon, as is the case in most of these films, suffices with a cameo. (Pluto TV)
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1. “Good Will Hunting” (1997): Readers crowned this movie the winner of our Massachusetts Movie Madness bracket last year, and for good reason. The story of a genius working as a janitor at MIT is great on its own. But the film’s legacy is as much about the story on screen as it is the story of two local boys who made good. (Prime Video)
End Credits
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Until next time, good stream hunting, everyone!
— Kevin
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