“Matt gave acting a framework, an integration into the social hierarchy at school,” Affleck said in an interview with Parade. “Before Matt, I was by myself. Acting was a solo activity where I’d just go off and do something, act in a little TV show or something, and no one understood it.”
That changed when Damon appeared.
“All of a sudden, I had this friend, Matt, and he gets it and wants to do it and thinks it’s interesting and wants to talk about it,” Affleck said. “Soon both of us are doing it.”
The pair began auditioning together and both appeared in the 1992 film School Ties. Their roles were far from the commanding leads that would later define their careers, but the film gave them an early shared credit — and evidence that their Boston plan was not entirely fanciful.
Good Will Hunting turned friendship into a Hollywood origin story
The partnership became famous through Good Will Hunting, the drama Damon and Affleck co-wrote and starred in. Released in 1997, the film transformed them from working actors into one of Hollywood’s most recognisable creative teams.
They played close friends in the film, drawing an obvious line between their real relationship and the story on screen. The screenplay won a Golden Globe and, in 1998, the Academy Award for Best Original Screenplay.
Their excited joint Oscar speech captured both the scale of the moment and how little either man appeared prepared for it.
“Ha! I just said to Matt that losing would suck and winning would be really scary, and it’s really, really scary,” Affleck said as the pair began thanking colleagues, friends and family while reminding each other whom they had missed.
The image stuck: two young friends from Boston had written themselves into Hollywood, then arrived at the Oscars together to collect the proof.
They reunited on screen the following year in Kevin Smith’s Dogma, but their careers increasingly developed along separate tracks. Damon became closely associated with the Bourne franchise and a run of major dramas, while Affleck moved between acting, writing and directing.
The friendship, however, remained part of their public identities even when they were not sharing a film set.
The partnership expanded beyond acting
Damon and Affleck turned their early success into a longer-running production relationship. They launched Pearl Street Films and worked together on projects including HBO’s Project Greenlight, a documentary series following first-time filmmakers.
The programme originally ran from 2001 to 2005 before returning in 2015. It placed the pair on the other side of the Hollywood gate, helping select and oversee emerging directors rather than attempting to persuade studios to take a chance on them.
They also continued appearing together at industry events, charity functions and, inevitably, Boston Red Sox games. When Damon received the American Cinematheque Award in 2010, Affleck attended with his then-wife Jennifer Garner, who described the two men as “the actual prototype for the great Hollywood bromance.”
Damon has offered a less polished explanation for why the relationship lasted.
“I’ve known him for 35 years, and we grew up together,” he told Entertainment Tonight. “We were both in love with the same thing — acting and filmmaking. I think we fed on each other’s obsession during really formative, important years and that bonded us for life.”
The industry eventually made the label official, or as official as such a label can be. In 2016, Spike TV’s Guys’ Choice Awards named them “Guys of the Decade.” Hollywood has created awards for less durable achievements.
New films brought Damon and Affleck back together
The pair returned to screenwriting with The Last Duel, collaborating with filmmaker and writer Nicole Holofcener. Damon said at the 2019 Toronto International Film Festival that it was the first time he and Affleck had written together in 25 years.
“We wrote for the first time in 25 years with Nicole Holofcener, who is a hero of ours — amazing writer, she’s great,” Damon told Extra. “The three of us wrote this thing, so hopefully we will shoot it next year.”
The historical drama was released in 2021, with both men appearing in the film. Damon’s wife, Luciana, joined them at its New York premiere, reflecting how the friendship had expanded to include their families.
Two years later, Affleck directed Air, the story of Nike’s pursuit of Michael Jordan. Affleck played company co-founder Phil Knight, while Damon starred as basketball executive Sonny Vaccaro. The film premiered at South by Southwest in 2023.
Their Boston roots then received a more knowingly ridiculous tribute in 2024. Damon joined Affleck and former New England Patriots quarterback Tom Brady as the “DunKings” in a Dunkin’ Super Bowl commercial, complete with coordinated outfits and little concern for personal dignity.
The Rip adds another chapter to a 40-year friendship
By early 2026, Damon and Affleck were back on the road together promoting The Rip. Their appearances included an interview on NBC’s Today and the film’s New York premiere at Alice Tully Hall.
The press tour also showed why their off-screen dynamic remains so marketable. During an appearance on The Howard Stern Show, Damon recalled learning that his wife had initially considered Affleck the more attractive of the two after seeing Good Will Hunting years before they met.
“This is f---ing completely true,” Damon said. “After we’d been together for a little while, probably a few months, she admitted that — I think I met her best friend from high school and it came out that the two of them went and saw Good Will Hunting together and her best friend thought I was the cute one and she thought Ben was the cute one.”
Affleck said he had never sensed the same enthusiasm from Luciana in person.
“I never got that vibe from her,” he joked. “So I think something I did in real life rubbed it off.”
“Finally she met him and all that went away,” Damon replied.
The exchange was teasing, but it also illustrated the ease that comes from knowing someone long before awards, franchises and red carpets complicated the picture.
The Rip is another entry in an unusually persistent collaboration, but the larger story is not simply how often Damon and Affleck work together. It is that the shared obsession they discovered as children still appears to be intact — only now the auditions have become premieres, and the two drama geeks are the people deciding which films get made.
