For Matt Damon and Ben Affleck, a life-long friendship has also fostered an award-winning, critically acclaimed creative partnership and a rich shared body of work. Since 1989, Damon and Affleck have appeared in nine movies together, including Good Will Hunting, a coming-of-age film the pair not only starred in, but wrote the screenplay for, resulting in their first Oscar wins for Best Screenplay in 1998. Their latest collaboration is Air, which released in theaters on April 5 and centers on the true story of how Michael Jordan signed an industry-changing shoe deal with Nike. In the film, Damon plays sports marketing executive Sonny Vaccaro, who recruited Jordan for the now-legendary Nike deal, while Affleck, who directed the film, portrays eccentric Nike co-founder Phil Knight.
Air marks a new era of creative collaboration for the duo, who recently teamed up to create Artists Equity, a production company that seeks to give its cast and crew a fair share of the profits of the movies made; at the company, Affleck is the chief executive, while Damon is the head of content. But this new stage of their careers is just another milestone in a bromance for the ages. The duo met over 40 years ago as children in Cambridge, M.A., outside of Boston, and knew their friendship was the real deal after Affleck defended Damon in a school yard fight. As teenagers, they pursued film careers together, traveling from Boston to New York City for auditions. Once they broke into Hollywood, the two continued to support each other’s work and often pursued projects that allowed them to work together both on and off the screen.
Read more: How Air Tells the True Story of Michael Jordan’s Nike Shoe Deal
“This friendship has been essential and defining and so important to me in my life,” Affleck told Damon in a 2022 Entertainment Weekly interview. “There were a few critical times, which are private and I don’t want to share, but where your support was so profoundly meaningful to me that I don’t think I would’ve been able to be successful without it.”
Here’s a look back at every Matt Damon and Ben Affleck movie.
Field of Dreams (1989)
The duo made their big screen debut as uncredited extras in Field of Dreams. According to an interview with Damon on the Dan Patrick Show, the main reason why they were in the film was because the call for extras was at the Red Sox’s baseball arena, Fenway Park.
“Just to go to Fenway,” Damon said. “We were extras in ‘Field of Dreams.’ I bet there were probably 3,000 extras in a big crowd scene when Kevin Costner and James Earl Jones are at the baseball game.” Damon also said that their first film experience had a big impact on them, including getting to meet Costner.
“Costner came out and hung out with the extras,” he said. “And Ben and I went and struck up a conversation with him. And he probably gave us five minutes. He was incredibly generous with his time.”
School Ties (1992)
Affleck and Damon’s next film together was School Ties, where they co-starred as Chesty Smith and Charlie Dillon, two anti-semitic bullies who target David Green (played by Brendan Fraser), a Jewish classmate, at their prestigious prep school.
Good Will Hunting
With Good Will Hunting, Affleck and Damon established themselves as not just talent on the silver screen, but behind-the-scenes as well. Damon stars as the titular character, a mathematic genius who works at MIT as a janitor, while Affleck played his friend, Chuckie. The pair wrote the screenplay together, with Damon beginning the initial script while a student at Harvard; the film draws inspiration from their shared upbringing in the Boston area.
“We came up with this idea of the brilliant kid and his townie friends, where he was special and the government wanted to get their mitts on him,” Affleck said of the film during a 2013 interview with Boston Magazine. “And it had a very Beverly Hills Cop, Midnight Run sensibility, where the kids from Boston were giving the NSA the slip all the time.”
The film became a critically acclaimed darling, garnering the pair a Golden Globe award and an Oscar for Best Screenplay.
Chasing Amy (1997)
Affleck and Damon appeared on-screen together yet again in Chasing Amy, a film that centers on the romantic woes of Holden McNeil, played by Affleck, who falls for Amy, a lesbian; Damon has a bit part as a business executive. While the film hasn’t aged well, especially in relation to its depiction of sexuality, it’s largely considered a cult classic as part of the Kevin Smith (better known as “Silent Bob”) Clerks cinematic universe.
Read more: We Don’t Deserve Ben Affleck
The duo appeared in another film for the Clerks film world with Dogma, the fourth film in the series, which centers on Damon and Affleck as Bartleby and Loki, two fallen angels who are banished to live in Wisconsin.
Jay and Silent Bob Strike Back (2001)
In Jay and Silent Bob Strike Back, the fifth movie in the Clerks film series, Damon and Affleck’s on-screen roles get meta. The pair co-star as themselves, as well as their respective characters from Good Will Hunting and Affleck reprises his role as the hapless Holden from Chasing Amy.
Jay and Silent Bob Reboot (2019)
Eighteen years after their last appearance in a Clerks film, Affleck and Damon appeared in the aptly named Jay and Silent Bob Reboot. For this film, Affleck reprised Holden from Chasing Amy yet again, while Damon plays his Loki character from Dogma, but with a tongue-in-cheek twist—the fallen angel is also Jason Bourne, a wry nod at Damon’s immensely popular film persona.
The Last Duel (2021)
With The Last Duel, Affleck and Damon starred as French noblemen caught up in a battle for honor. Damon starred as Sir Jead de Carrouges, a nobleman who’s so obsessed with securing the approval of his liege lord, Count Pierre d’Alencon, played by Affleck, that he’s an absent husband to his wife, who claims she is raped by a knight.
Read more: Matt Damon Wants You Care About Water
In Air, the pair reunite on screen again for the first offering from their production company, Artists Equity. Centering on the story of how Michael Jordan signed his now-legendary shoe deal with Nike, the film stars Damon as Sonny Vaccaro, the sports marketing executive who was the architect of the deal and co-stars Affleck, who also directed the movie, as Phil Knight, the co-founder of Nike.