Summary

• Damon and Affleck first started as extras in "Field of Dreams" in 1989 before co-writing and co-starring in "Good Will Hunting" in 1997.
• The actors continued collaborations with movies like "Dogma" and "Jay And Silent Bob Strike Back" over the years before starting their own production company, Artist's Equity, in 2022.
• The first film released under Artist's Equity, "Air," directed by Affleck and starring Damon, delves into the true story behind the creation of Nike's Air Jordans.

Matt Damon and Ben Affleck are two of Hollywood's most beloved collaborators who've made ten films together over the years. The pair grew up as childhood friends in Boston, helping each other find their footing in the film world throughout the 1990s. Good Will Hunting is still their most notable collaboration, where they co-wrote and co-starred in the classic film, winning the pair their first Academy Awards in their late 20s. In the 2020s, they've finally returned to collaborating on major projects together, though they've had several minor appearances together over the years.

In 2022, Damon and Affleck teamed up to start their own film production company, Artist's Equity, where they'll be working closely on projects for years to come. The company's first film, Air, was one of the best drama movies of 2023, with Damon starring and Affleck directing and playing a ing role. Their next collaboration, a crime film titled Animals, is set to release on Netflix, with both stars appearing in the film and Affleck behind the camera once again.

The list is ordered chronologically, from their first collaboration in 1989 to their most recent in 2023.

10 Field Of Dreams (1989)

Damon & Affleck Were Extras In Kevin Costner's Baseball Classic

The first movie Matt Damon and Ben Affleck appeared in together is an iconic one, however, their presence in the movie is not exactly noteworthy. The actors both appeared as extras in the Kevin Costner baseball film Field of Dreams.

In an interview with Dan Patrick, Damon shared his experience appearing in the film, explaining that the young actors took the gig just so they could go to Fenway Park, the baseball stadium of the Boston Red Sox.

With thousands of extras in the scene, it'd be impossible to actually spot the pair, though Damon mentions that they got to spend a few minutes with Costner, picking his brain about the film industry years before they'd become superstars in their own right. Recently, Costner revealed that he does Affleck and Damon on the Field of Dreams set despite the fact that they were unknown actors at the time.

9 School Ties (1992)

A Prep School Drama Exploring Anti-Semitism In 1950s America

Even before Good Will Hunting made them superstars, Damon and Affleck were beginning to find some success in film roles in the '90s. The 1992 film School Ties saw the two in their first prominent roles, acting with other young stars like Brendan Fraser, Chris O'Donnell, and Cole Ha. While Damon's part is much bigger than Affleck's, it was still a significant step in both of their careers, setting the tone for the types of films they'd be in leading up to their rise to stardom.

Before breaking out in Good Will Hunting, Affleck continued to land parts in teen "slacker movies," a subgenre of the 1990s that primarily included the works of directors like Richard Linklater and Kevin Smith. Affleck continued to have ing roles in similar movies to School Ties, such as Dazed and Confused and Mallrats. Damon and Affleck's School Ties co-star, Cole Ha, also appeared as part of their friend group in Good Will Hunting and co-starred with Affleck in Dazed and Confused. Even if it's not their most prominent movie, School Ties was essential to their budding careers.

School Ties is set in the 1950s and stars Fraser as a young Jewish man who earns a scholarship to go to an elite prep school. He is initially accepted by the others as a popular student and an accomplished athlete. However, when Damon's jealous character discovers Fraser's Jewish heritage, he reveals it to the others who turn on him with vile antisemitism. Not only is it interesting to see Damon and Affleck so early in their career but also playing such unlikable characters.

8 Glory Daze (1995)

A '90s Indie Slacker Movie

Another of the 1990s slacker movies, the 1995 film Glory Daze, featured Ben Affleck in his first starring role. Different from School Ties, where he starred, Matt Damon appears in Glory Daze in a very minor role, not even speaking.

The movie seems to try to be capturing the same vibe as Affleck's earlier and more successful film, Dazed and Confused, following a group of friends at college who face the idea of breaking up and going their separate ways with graduation approaching.

It's not the most well-reviewed film, but it's still a fun watch for fans of the '90s independent slacker genre, and Damon and Affleck are among the famous faces that can be spotted in it. Sam Rockwell and John Rhys-Davies play roles in the movie, and Matthew McConaughey and Brendan Fraser also appear very briefly. Though they were both becoming more established actors, it is interesting to see they were already popping up in each other's movies in smaller roles just for the fun of it.

7 Good Will Hunting (1997)

A Quintessential Coming-Of-Age Romance

For Matt Damon and Ben Affleck, Good Will Hunting was the pivotal film that launched them into Hollywood stardom. Famously, Affleck and Damon wrote the movie to give themselves quality roles that Hollywood wasn't offering them at the time. Good Will Hunting stars Damon as a math genius working small jobs in Boston until his talents are discovered, giving him a path to a brighter future. Affleck costars as his best friend.

Much of the film's strength comes from Damon and Affleck's sharp writing.

Damon's career instantly flourished, receiving prominent roles from filmmakers like Steven Spielberg and Steven Soderbergh in the following years. Affleck also had a slew of blockbuster films, though it took more time for him to receive his fair dues as a filmmaker and screenwriter. However, Affleck's performance in the movie is also underrated as he delivers a famous speech.

Widely considered one of the best movies of the 1990s, Good Will Hunting proves that a film can be highly entertaining through the power of script and performance. Much of the film's strength comes from Damon and Affleck's sharp writing, which strengthens the incredible performances of Damon and star Robin Williams. Good Will Hunting's many great quotes, from the powerful to the hilarious, have added to its popularity and relevancy while showing the actors to be an excellent writing duo, something they would not do again together for decades.

6 Chasing Amy (1997)

An Indie Rom-Com From Kevin Smith

Like Glory Daze, the 1997 film Chasing Amy is a Ben Affleck-led movie with a minor cameo from Matt Damon. Directed by Kevin Smith, who'd become a frequent collaborator with the two stars, Chasing Amy hasn't aged particularly well but was an important role for Affleck to get him out of the bully/villainous roles and become more of a likable leading man.

The movie stars Affleck as a comic book writer who falls for a girl (Joey Lauren Adams) only to discover that she is a lesbian. Carrying on a friendship with her, he attempts to convince her that he is the one she should be with. The film has its strengths as an independent romantic comedy, but Kevin Smith is out of his depth writing a story about LGBT characters. However, Affleck is very strong in the funny, sweet, and layered leading role. Damon appears in one scene as an executive trying to buy the rights to Affleck's comic.

5 Dogma (1999)

A Kevin Smith Comedy With Fantastical & Religious Elements

Dogma was the next Kevin Smith movie in which Damon and Affleck collaborated, both taking on much larger roles. Smith goes for an ambitious story that mixes Biblical elements and rich mythology with the kind of juvenile humor and pop culture gags he is mostly known for. Affleck and Damon star as two fallen angels living aimless lives on Earth when they discover a loophole that they think will allow them to return to heaven. However, it will really cause the end of existence which leads to a band of heroic misfits setting out to stop them.

Damon is very funny as the unhinged and vengeful angel while Affleck is excellent as the movie's complex villain.

The 1999 film was the last time Damon and Affleck starred in a film together in leading roles for decades; as their careers expanded, they tried to pursue individual projects, feeling that they'd be limited by continuously working with each other. Dogma is a comedy film with fantastical elements, revolving around the star duo as fallen angels who are banished from Heaven and sent to Wisconsin. Damon is very funny as the unhinged and vengeful angel while Affleck is excellent as the movie's complex villain.

4 Jay And Silent Bob Strike Back (2001)

Damon & Affleck Appear In A Meta Cameo

In 2001, both Damon and Affleck made cameo appearances in Kevin Smith's Jay and Silent Bob Strike Back which was meant to be the closing chapter of his View Askewniverse cinematic universe and thus brought many of the characters from these movies together. The movie follows Jay and Silent Bob as they head out on a road trip to stop a Hollywood from making a movie out of the comic book characters they inspired, Bluntman and Chronic.

While the film itself isn't one of the best Kevin Smith movies, their cameo appearances make it worth the watch. The two stars appear as themselves in a scene where they're shooting a fake Good Will Hunting sequel, joking about themselves selling out. They re-create the bar altercation scene from the original movie with a hilarious comedic twist, even including filmmaker Gus Van Sant in the sketch.

3 Jay And Silent Bob Reboot (2019)

Another Kevin Smith Comedy With Meta-Commentary On Reboot Culture

2019's Jay and Silent Bob Reboot, not to be confused with the previous, similarly named rendition, is another Kevin Smith film where Damon and Affleck make brief cameo appearances. The Jay and Silent Bob movie followed the stoner duo as they set out on yet another road trip, this time looking to stop a reboot of the Bluntman and Chronic movie.

Affleck appears as himself in a monologue scene where he makes references to playing Batman and his role in Chasing Amy. Matt Damon's cameo scene has him pick up his role from Dogma, joking that he played a character named Loki in a movie before Tom Hiddleston made it cool. Unfortunately, Smith's writing is not as sharp as in the previous two collaborations and these cameos, along with many of the others in the movie, feel much more forced.

2 The Last Duel (2021)

A Medieval War Film From Ridley Scott

Matt Damon and Ben Affleck's first prominent collaboration in over 20 years was for The Last Duel. The pair co-wrote the film alongside Nicole Holofcener, their first filmed script together since winning the Oscar together more than two decades earlier. To add to the pedigree of the movie, Ridley Scott directed the medieval epic. Matt Damon stars with Jodie Comer and Adam Driver, and Affleck appears in a significant ing role.

The movie is loosely based on a true story about two rival knights (Driver and Damon) who find themselves in a deadly confrontation when Damon's wife (Comer) makes a shocking accusation. The story is told through the perspective of the three main characters, each with a different view of the events. It's a great historical epic that bombed at the box office, but the movie received rave reviews and many called it an underrated gem. While Affleck's performance as a count overseeing the feud was nominated for a Razzie, many defended it as a highlight of the movie.

1 Air (2023)

A Biographical Drama About The World Of Sports & Fashion

The first film from Matt Damon and Ben Affleck's production company is also the first time Affleck directed Damon in a movie. The movie delves into the true story of how Nike was able to persuade Michael Jordan to sign with their company which led to the creation of the iconic sneaker line, Air Jordans. Damon stars as the talent scout who worked to put the deal together while Affleck plays a ing role as the CEO of the company, Phil Knight.

Air wasn't a box office success, but it was a well-reviewed movie. The two stars are at their best with intelligent dialogue and performance-driven films, and Air has set the precedence for the style of films Artists Equity will be producing. The duo also spoke openly about how much they enjoyed the writing process together (though they didn't take credit for their rewrites) which could mean another collaboration like this won't be long.