Every Ben Affleck and Matt Damon Movie Collaboration, Ranked Worst to Best

With the recent news that Ben Affleck and Matt Damon will be collaborating again for an upcoming movie called The Rip, the world is excited about their collaboration again.

From their debut in Good Will Hunting to their latest project, being Air, Matt Damon and Ben Affleck have been the best of friends in Hollywood for several decades. However, the two have indeed collaborated on numerous projects throughout the year.

Naturally, we decided to rank them from worst to best. So, without further ado, here is every Ben Affleck and Matt Damon movie collaboration, ranked from worst to best.

10. Field of Dreams

Being uncredited extras in the film, Field of Dreams, was a 1989 family/sports film that featured Matt Damon and Ben Affleck as extras. The two appear during the scene at Fenway Park. They were two of the extras in the plethora of people in the backdrop, evidence of the actors’ earlier struggling days.

They even revealed to EW that it was a surreal experience watching James Earl Jones and Kevin Costner at Fenway Park.

It was, like, seeing, you know, God, Him [Kevin Costner] and James Earl Jones. We went, and it was like two days in Fenway Park. Everything about it felt so big time, and I remember, we thought we knew that actors were kind of fraudulent, and Costner took batting practice.

The only reason why Field of Dreams is at #10 on this list is that they were simply extras in the film and were uncredited.

9. Chasing Amy

Another film that featured Ben Affleck and Matt Damon, Chasing Amy wasn’t a famous flick, especially considering Affleck and Damon hadn’t yet found fame with their projects.

However, the film did star Affleck in the leading role of Holden McNeill, whose girlfriend turns out to be a lesbian. Being a rom-com film, Chasing Amy featured Damon in a cameo role where he portrays the role of an unnamed executive who encounters Affleck along the way.

Naturally, not being an equal opportunity for both stars, Chasing Amy remains at #9 on this list.

8. Glory Daze

Glory Daze was a 1995 indie film that explored themes of friendship. The film stars Ben Affleck in the role of Jack, alongside Matt Damon (who has a much smaller role) as Edgar Pudwhacker.

Jack is a soon-to-be graduate who emotionally struggles with leaving his college life behind, while Damon’s role remains more like a cameo in the film. This was also before fame had knocked on their doorsteps, and the two were trying to make it big in Hollywood.

The only reason it remains #8 on this list is that the storyline was much better than the previous two films.

7. Jay and Silent Bob Strike Back

A comedy/stoner film from 2001, Jay and Silent Bob Strike Back featured Matt Damon and Ben Affleck playing themselves in the movie. During a brief segment, the two protagonists stumble upon the sets of Good Will Hunting where Affleck and Damon are shooting their scenes.

Although both characters had minor roles, the meta commentary on the success of Damon and Affleck post Good Will Hunting was something out of the blue and quite apt to the 2001 flick.

Naturally, Jay and Silent Bob Strike Back got the #7 on this list.

6. Dogma

Probably one of the best flicks in the 1990s that starred Matt Damon and Ben Affleck in leading roles, Dogma was a 1999 film that was part of the View Askewniverse (including Jay and Silent Bob Strike, Jay and Silent Bob Reboot, and Chasing Amy).

The film featured the two stars as fallen angels Bartleby (Affleck) and Loki (Damon). They find a loophole that allows them to re-enter the Kingdom of Heaven, but also prove God as fallible and non-existent.

The film is a satirical take on the world, which explores themes of faith and redemption. Naturally, Dogma stands at #6 on this list.

5. Jay and Silent Bob Reboot

A closure to the Askewniverse, Jay and Silent Bob Reboot is a 2019 film with the two protagonists reprising their roles alongside Matt Damon and Ben Affleck.

Bring the multiverse into this singular movie, Damon reprises his role of Loki from Dogma, while Ben Affleck portrays the role of Holden McNeill from Chasing Amy.

Both had cameo roles, but Affleck’s reprisal as Holden McNeill came at a pivotal moment in the film, which also brought his character closure after the events of Chasing Amy.

With Damon and Affleck reprising different roles and the hint of a multiverse in it, Jay and Silent Bob Reboot stands at #5 on this list.

4. School Ties

Despite not being famous, School Ties featured Matt Damon in an antagonistic role while Ben Affleck portrayed a supporting character to the protagonist.

School Ties condemns antisemitism as the protagonist is discriminated against when his Jewish roots are revealed in an elite school. Damon’s character portrays the worst of the jokes and discrimination against the protagonist, while Ben Affleck’s role is that of a supporting character.

Despite not having equal amounts of roles, the film’s strong narrative and the deep exploration of its controversial theme make it their 4th best collaboration on-screen.

3. Air

We are in the big leagues now. Directed by Ben Affleck and starring Matt Damon in the leading role, Air is a 2023 film that depicts the story of Sonny Vaccaro.

A salesperson who works in a major shoe company, Sonny Vaccaro, sees an opportunity to elevate business by designing special shoes for a rookie Basketball player named Michael Jordan.

Alongside Damon, Ben Affleck also stars in the film in the role of Phil Knight, the co-founder and CEO of Nike. Although in a supporting role, the chemistry between Damon and Affleck was quite visible, and with Affleck helming the project as the director, Air was bound to be #3 on this list.

2. The Last Duel

Following their screenplay writing in the 1997 flick, Good Will Hunting, Matt Damon and Ben Affleck reunited after decades to write the screenplay of The Last Duel together.

A rather controversial choice, but Damon’s portrayal of Sir Jean de Carrouges and Affleck’s role as Count Pierre d’Alençon were praised, and the dialogues were sharp with characters that spoke volumes through their emotions rather than their words.

Although they don’t have extensive scenes together, their acting prowess (they play opposite characters in the movie) is quite commendable.

1. Good Will Hunting

Finally, the film that started it all. Good Will Hunting wasn’t exactly the debut movie of Matt Damon or Ben Affleck, but it is the movie that skyrocketed them to fame in Hollywood.

Being young, the two wrote a screenplay together about a janitor at MIT who is a genius but doubts his own abilities. The film also roped in Robin Williams for an iconic role, while the MIT genius character was given to Matt Damon.

Throughout the film, Ben Affleck portrays the role of Damon’s friend who teaches him about self-confidence and makes him believe in his self-worth. The duo won an Oscar for Best Original Screenplay (and they are one of the youngest people to do so).

Naturally, the film that became the breakthrough movie (with an Oscar to its name) should prove to be the best collaboration between Matt Damon and Ben Affleck.

To top it all off, of course, we have the upcoming iconic Netflix film, The Rip, which will once again star Ben Affleck and Matt Damon in leading roles.

Are you excited for yet another Affleck-Damon collaboration? Let us know your thoughts in the comments below.

The Rip will release on January 16, 2026, on Netflix (USA).