You likely already know that Ben Affleck and Matt Damon have been friends since they were kids, growing up together in Cambridge, MA. But how did their relationship progress from the playground to Hollywood? Well, the pair first became close when they were in high school, partially because they had the same interests (especially a desire to head into acting). After a few years as working actors – including some movies together – the duo collaborated on the script for “Good Will Hunting,” and the rest of history.
The movie became a smash success, with rave reviews not just for their performances but also for the screenplay they wrote together, which won them both an Oscar. In the years since, Affleck and Damon have teamed up for even more movies, including “Dogma,” “The Last Duel,” and the upcoming “Air,” which Affleck is directing.
The duo have stayed close through the years, supporting each other as they both became fathers and navigated marriages. “This friendship has been essential and defining and so important to me in my life,” Affleck told Damon in a January 2022 interview with Entertainment Weekly. “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.”
Ahead are the nine movies Damon and Affleck have appeared in together, in chronological order.
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"Field of Dreams" (1989)
Affleck and Damon were just teens when they got gigs as extras in 1989’s “Field of Dreams.” It was when the duo were living in Massachusetts, though they frequently traveled to New York for acting parts. They responded to a call for extras at Fenway Park for a very simple reason: “Just to go to Fenway,” Damon told Dan Patrick in 2021. “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.”
Despite their small role, they did get a chance to talk to the film’s lead, Kevin Costner. “Costner came out and hung out with the extras,” Damon recalled. “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.”
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"School Ties" (1992)
Affleck and Damon starred in “School Ties” alongside Brendan Fraser in 1992. In the movie, which is set in the 1950s, Fraser plays David Greene, a Jewish high school student who gets an athletic scholarship to prep school. There, most of the school and staff are anti-Semitic, and he struggles. Damon plays David’s main antagonist, Dillon, while Affleck plays Chesty Smith.
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"Good Will Hunting" (1997)
“Good Will Hunting,” released in 1997, was Affleck and Damon’s big break. Set in their hometown, Damon played a self-taught genius, Will Hunting, who works as a janitor at MIT. He connects with Dr. Sean Maguire, played by Robin Williams, who urges him to seek more for his life. Affleck plays Will’s friend Chuckie Sullivan, who wants his friend to reach for more and move on. Minnie Driver plays Will’s love interest Skylar and Affleck’s brother Casey also appears in the film.
Affleck and Damon wrote the script together and had to fight hard to be cast in the film. They ended up winning the Academy Award for best screenplay, written directly for the screen, for their efforts, and Williams won best supporting actor.
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"Chasing Amy" (1997)
“Chasing Amy,” released in 1997, stars Ben Affleck as Holden McNeil, who meets and falls for Alyssa, played by Joey Lauren Adams. But Amy is a lesbian, and Holden can’t handle that. Silent Bob (director Kevin Smith) warns him that he was in a similar relationship with a girl named Amy, and he felt like he was always chasing her. Damon appears in the film as an executive. “Chasing Amy” is Smith’s third movie set in the universe he created with 1994’s “Clerks.”
The indie film became a box-office smash, though many have criticized its portrayal of Alyssa’s sexuality and the fact that the movie doesn’t use the word “bisexual.”
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"Dogma" (1999)
In 1999’s “Dogma,” which was also directed by Smith and is the fourth movie set in the “Clerks” universe, Damon and Affleck play two fallen angels, Bartleby and Loki, who are condemned to exile in Wisconsin. The cast also includes Linda Fiorentino, Salma Hayek, Alan Rickman, Chris Rock, George Carlin, and Jason Mewes and Smith as their recurring characters Jay and Silent Bob. The film made $30 million at the box office on a $10 million budget. The Catholic League denounced the film as blasphemous, though the Catholic Church itself never commented.
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"Jay and Silent Bob Strike Back" (2001)
“Jay and Silent Bob Strike Back” is Smith’s fifth movie, again set in the Clerks realm, and Jay and Silent Bob take center stage again. Affleck appears as himself, his “Good Will Hunting” character, and as Holden from “Chasing Amy.” Damon appears as himself and as Will Hunting. The film’s sprawling ensemble includes Carrie Fisher, Jon Stewart, Tracy Morgan, and Alanis Morissette. Adams also reprises her role as Alyssa from “Chasing Amy.”
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"Jay and Silent Bob Reboot" (2019)
“Jay and Silent Bob Reboot” in 2019 saw Affleck and Damon return to Smith’s universe once again. Affleck plays his “Chasing Amy” character, and Damon is Loki, a fallen angel who was also Jason Bourne, a joke about Damon’s Bourne franchise. Adams returns once again as Alyssa, and Smith’s daughter Harley Quinn Smith play’s Jay’s estranged daughter.
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"The Last Duel"
“The Last Duel,” released in 2021, marked the duos return to a drama film, together. In the movie, based on a true story, Damon plays Sir Jean de Carrouges, a member of the French nobility who’s anxious to make a name for himself. He marries Marguerite de Carrouges, played by Jodie Comer, but he’s a neglectful husband obsessed mostly with pleasing and getting the approval of his liege lord, Count Pierre d’Alençon (Affleck). Adam Driver plays Jacques Le Gris, who Marguerite accuses of raping her when Sir Jean is not home. The movie tells the story from Sir Jean, Jacques, and Marguerite’s perspectives before culminating in the titular duel and its aftermath. The film was directed by Ridley Scott.
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"Air" (2023)
“Air” marks the first time Affleck is directing Damon, and Affleck stars in the movie with his bestie. (It’s the third time Affleck’s directed himself after 2010’s “The Town” and 2012’s “Argo.”) The movie tells the story of how Nike signed Michael Jordan and began its Air Jordan brand, saving the company and making Jordan a cultural icon. Damon plays marketing executive Sonny Vaccaro with Affleck as Nike founder Phil Knight. Viola Davis plays Jordan’s mother Deloris.
