
Matt Damon and Ben Affleck are back together on screen in the new Netflix film, The Rip. The longtime friends and collaborators play Miami detectives who are offered a lot of money to compromise their integrity. This crime thriller, directed by Joe Carnahan, is just the latest in a long career of successful films for both Academy Award-winning actors, and The Rip is already receiving good reviews, proving once again that Damon and Affleck make a great team.
Damon and Affleck have appeared together in many films, sometimes as equals and other times with one in a brief appearance. When judging all their movies together, even small roles can be surprisingly important, often more so than what critics said. Of course, truly bad movies also affect the ranking. Considering all of this, and with their new film, The Rip, being well-received, how will it stack up against their other collaborations?
13
‘Field of Dreams’ (1989)

Universal Pictures
While Field of Dreams isn’t a poorly made film and is generally quite good, it ranks lower on this list because the involvement of Damon and Affleck was minimal. The movie’s quality isn’t the issue; it’s their small part in it.
Damon and Affleck both had small, uncredited roles as extras in the baseball scenes filmed at Fenway Park. They were paid to be part of the crowd, helping to fill out the stadium’s bleachers. While Field of Dreams is a fantastic and highly recommended film, the involvement of these two actors doesn’t quite elevate it to the level of their other work.
12
‘Glory Daze’ (1995)

Fusion Studios, Inc./Woodward Productions
Glory Daze marked Ben Affleck’s first leading role, where he portrays a college student at UC Santa Cruz navigating life after a breakup. The film also includes early appearances by several now-famous actors like Matthew McConaughey, Brendan Fraser, John Rhys-Davies, and Sam Rockwell. Even Matt Damon makes a brief, silent cameo as one of Affleck’s character’s old roommates.
Glory Daze is an unremarkable film that hasn’t stood the test of time and is largely forgettable. Although Ben Affleck stars, Matt Damon has a small role. Because the film isn’t well-remembered, it doesn’t significantly contribute to either actor’s career, and one actor’s subsequent success far overshadows it.
11
‘The Third Wheel’ (2002)

Miramax
The romantic comedy The Third Wheel features Luke Wilson and Denise Richards, with a small role for Ben Affleck. Affleck plays a friend who pushes Wilson to ask Richards, his coworker, on a date. While not a leading character or particularly charming, Affleck has more screen time than Matt Damon, who makes a quick, surprising cameo appearance before disappearing from the film. Melissa McCarthy also appears in a minor role.
While not a great movie, The Third Wheel is a fairly standard romantic comedy, and Ben Affleck and Matt Damon don’t play the main roles. It’s a little funnier than Glory Daze, though, which gives it a slight edge.
10
‘Jersey Girl’ (2004)

Miramax
Jersey Girl is one of the films where Ben Affleck and Matt Damon collaborated with writer-director Kevin Smith. In the movie, Affleck plays a single dad struggling to cope with the loss of his wife while balancing work and raising his daughter. When it was first released, Jersey Girl received a lot of criticism. The intense media attention on Affleck’s relationship with Jennifer Lopez, who played his late wife in the film, overshadowed the movie itself, and many found it to be overly sentimental.
Although Jersey Girl wasn’t a hit with audiences, it’s actually more entertaining than some of Ben Affleck’s other early films, like Glory Daze and The Third Wheel. Matt Damon appears briefly as an executive interviewing Affleck’s character, which is a funny scene, but doesn’t really improve the movie overall.
9
‘Jay and Silent Bob Reboot’ (2019)

View Askew
In Jay and Silent Bob Reboot, Kevin Smith delivers his signature blend of raunchy humor and heartfelt moments, both as the writer and director. He cleverly uses his shared cinematic universe, known as the View Askewniverse, to revisit beloved characters from his previous films, featuring appearances by actors like Ben Affleck and Matt Damon.
Ben Affleck reprises his role as Holden McNeil, a character he originally played in Kevin Smith’s 1997 film, Chasing Amy. Though he appears in just one scene, it’s a highlight of Jay and Silent Bob Reboot. Matt Damon also makes a brief appearance in a single scene, returning as Loki, the angel he portrayed in 1999’s Dogma. These cameos enhance the film’s surprisingly delightful nature, but because they aren’t central to the story, it’s difficult to consider it among Smith’s very best works.
8
‘Jay and Silent Bob Strike Back’ (2001)

Miramax Films
Kevin Smith returns with another installment in his interconnected ‘View Askewniverse.’ This time, in a particularly hilarious cameo, Ben Affleck and Matt Damon play themselves. Jay and Silent Bob Strike Back follows the iconic duo as they travel to Hollywood to prevent a film adaptation of a comic book they inspired. Affleck appears both as his character Holden McNeil and as himself in the movie.
When Jay and Silent Bob arrive in Los Angeles, they wander onto various movie sets, including one for a fictional Good Will Hunting 2. The joke gets even better when they appear as exaggerated versions of their Good Will Hunting selves, even going so far as to pull out a shotgun. Although this scene is amusing, Jay and Silent Bob’s overall role in the movie is small, which unfortunately keeps Jay and Silent Bob Strike Back from being a standout film.
7
‘School Ties’ (1992)

Paramount Pictures
The movie School Ties remains relevant today because of its exploration of antisemitism and bullying, and many of the young actors in it have since become famous. Along with Matt Damon and Ben Affleck – who played a rival and a minor bully, respectively – the film stars Brendan Fraser, Chris O’Donnell, and Cole Hauser.
When School Ties came out, it was a touching and emotional film, and it gained a new audience years later thanks to its talented actors. Although it’s a well-made movie and showed a lot of potential for the careers of its stars, it doesn’t quite stand out compared to some of Ben Affleck and Matt Damon’s other, more successful collaborations, which have consistently impressed both critics and viewers.
6
‘The Rip’ (2026)

Netflix
In The Rip, Damon and Affleck deliver compelling performances as characters with questionable morals. Their strong on-screen connection is a major highlight, offering audiences a fresh perspective on these two actors. With its excellent acting and suspenseful plot, The Rip is a standout film that deserves recognition.
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Even with strong directing, Netflix’s crime film really relies on the chemistry of Damon and Affleck, which says a lot about their impact. While it might not be their best work, The Rip is still a very enjoyable thriller, and clearly benefits from the years of experience both actors bring to the genre, offering a fresh take on familiar themes.
5
‘The Last Duel’ (2021)

20th Century Studios
With The Last Duel, Ben Affleck and Matt Damon wrote a screenplay together for the first time, joined by Nicole Holofcener. The film tells its story in a distinctive way, revealing details through the memories of each character, but never offering a single, definitive version of events. Despite positive reviews, The Last Duel didn’t perform well in theaters and remains one of their most overlooked projects.
Ridley Scott’s film, The Last Duel, features memorable looks for Damon and Affleck and showcases the stunning visuals Scott is known for in historical epics. While the movie didn’t perform well at the box office, its quality is clear and it deserves to be more widely recognized. Even now, The Last Duel hasn’t gotten the attention it merits, potentially affecting its ranking among films. It’s a film well worth watching for those who haven’t seen it.
4
‘Chasing Amy’ (1997)

Does this story take place in the same world as Kevin Smith’s other films? Chasing Amy introduces Ben Affleck as Holden McNeil, a comic book writer who falls for a lesbian, and their relationship evolves from friendship to romance, despite being unlikely to last. The film is a romantic comedy-drama and helped launch Affleck’s career, marking an early success for director Kevin Smith.
Matt Damon makes a brief appearance in Chasing Amy as a company executive, at a time when he and Kevin Smith were both relatively unknown. Although a small role from Damon might usually hold a film back, Chasing Amy remains one of Smith’s most critically acclaimed movies, even if some parts haven’t aged well. This enduring quality allows Chasing Amy to stand out and rank higher than many other films.

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