The Definitive Ranking of Every Ben Affleck and Matt Damon Movie
Table of Contents
A comprehensive guide to the 13 films starring the iconic duo, from must-watch classics to skip-at-all-costs.
After the runaway success of “Good Will Hunting,” Ben Affleck and Matt Damon became a fixture in Hollywood, and in each other’s careers. Almost 30 years later, the childhood friends continue their collaboration, running a production company, making joint public appearances, and starring in films together – including their newest Netflix offering, “The Rip.” But with 13 films under their belts, knowing where to start (or what to avoid) can be daunting.
Recently, a review of “The Rip” sparked a conversation about the full Damon-Affleck filmography. As one observer noted, the pair’s collaborative history is surprisingly extensive, bolstered by frequent appearances in the films of director Kevin Smith. This prompted a deep dive into their collective work, ranking each film from essential viewing to those best left forgotten.
The Skip List: Damon & Affleck Films to Reconsider
Generally, films ranked 10-12 are best skipped, while those from 1-5 are worth your time.
12. “The Third Wheel” (2002): This largely forgotten romcom barely grossed $44,000. Affleck plays a coworker to Luke Wilson, while Damon makes a brief cameo as a jealous ex.
11. “Glory Daze” (1996): A Gen-X slacker film mirroring “Kicking and Screaming,” Affleck leads a group of recent graduates avoiding adulthood. Damon appears in a nonverbal role as “Pudwhacker.” Despite a strong soundtrack, the writing and ending fall flat.
10. “Jay and Silent Bob Reboot” (2019): A return to Kevin Smith’s View Askewniverse, featuring Damon and Affleck reprising their roles from “Dogma” and “Chasing Amy.” However, it fails to recapture the magic for those less devoted to Smith’s universe.
9. “Jersey Girl” (2004): This dramedy starring Affleck and Liv Tyler received undue criticism, largely due to the intense media coverage surrounding “Bennifer” (Affleck’s relationship with Jennifer Lopez). While not a masterpiece, it contains some genuinely funny moments and another Damon cameo.
8. “Jay and Silent Bob Strike Back” (2001): Smith’s satirical take on the film industry sees the titular duo attempting to stop a movie adaptation of their comic book alter-egos. Affleck plays multiple characters, including a memorable appearance alongside Damon filming a fictional “Good Will Hunting” sequel.
The Middle Ground: Damon & Affleck Films Worth a Watch If You’re Curious
7. “The Rip” (2026): Joe Carnahan’s latest film, now streaming on Netflix, is a bit slow-paced, but benefits from strong performances by Damon as an inscrutable narcotics cop and Affleck as his hotheaded subordinate.
6. “School Ties” (1992): A nostalgic favorite for many, this prep school drama filmed in Concord showcases a young Damon, Affleck, Brendan Fraser, Cole Hauser, and Chris O’Donnell. While heavy-handed in its messaging, the actors deliver compelling performances.
5. “Dogma” (1999): Kevin Smith’s religious spoof, starring Linda Fiorentino, features Affleck and Damon as fallen archangels banished to Wisconsin. A bold and often hilarious film, though the third act may not appeal to all viewers.
The Must-See Films: Damon & Affleck at Their Best
4. “Air” (2023): Affleck’s directorial effort, a biopic about Nike’s partnership with Michael Jordan, shines thanks to the chemistry between Affleck (as Phil Knight) and Damon (as Sonny Vaccaro). Jason Bateman and Chris Messina also deliver standout performances.
3. “The Last Duel” (2021): Ridley Scott’s medieval drama, presented through multiple perspectives, has grown in appreciation since its release. Damon delivers a nuanced performance as a knight, while Affleck provides comic relief as a boisterous lord.
2. “Chasing Amy” (1997): A groundbreaking romantic comedy that challenged conventions with its depiction of sexual fluidity. Affleck plays a comic book artist falling for a lesbian artist (Joey Lauren Adams), with Damon making a cameo appearance.
1. “Good Will Hunting” (1997): The film that launched Damon and Affleck into superstardom remains their most iconic collaboration. The story of a genius janitor at MIT is compelling on its own, but the film’s enduring legacy lies in the story of two local boys who achieved their dreams. Readers crowned this the winner of a recent Massachusetts Movie Madness bracket, and for good reason.
That concludes this edition of The Queue. If you enjoy these recommendations, please share this newsletter with your friends. Until next time, happy streaming!— Kevin
