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Ben Affleck and Matt Damon’s Bromance Hits a New High After 50

Will their new movie ‘Air’ send them back to the Oscars?

spinner image Ben Affleck and Matt Damon smile at each other while on the red carpet at the world premiere of the film Air in Los Angeles
(Left to right) Ben Affleck and Matt Damon attend the World Premiere of "Air" at the Regency Village Theatre in Los Angeles on March 27, 2023.
Alex J. Berliner/ABImages

For the first time, Matt Damon, 52, not only costars with his lifelong bestie Ben Affleck, 50, but is directed by him in Air, the new movie about Nike’s collaboration with a not-yet-famous Michael Jordan to launch the zillion-dollar Air Jordan shoe empire. Their friendship is longer than their marriages, and Jennifer Garner — Affleck’s wife before his current one, Jennifer Lopez — once joked, “Ben is half of one of the greatest love stories ever told — not with me — the actual prototype for the great Hollywood bromance.” Air is the first Amazon Studios film debuting in thousands of theaters (and streaming on some future date), and it earned a stellar 94 percent Rotten Tomatoes critics’ rating and $30 million its first week, better than expected at a time when adult-skewing movies are struggling. Film fans’ eagerness to see the pair collaborate again is one reason the much-buzzed Air is their likeliest flick to fetch Oscars since 1997’s Good Will Hunting. Here are some highlights of their lifelong friendship.

As kids, their moms put them together — and forced them to be creative

Affleck and Damon grew up two blocks apart in Cambridge, Massachusetts. Damon’s mom, a professor of childhood development, believed that it hampers kids’ creativity when they use cartoon- or movie-based toys to reenact their stories, so she raised him to make up his own stories and plays. (The one he wrote for his Harvard playwriting class became, with Affleck’s help, the screenplay for Good Will Hunting.) Damon’s mom knew Affleck’s mom, a schoolteacher of young children, “so I was pretty much forced into hanging out with Ben,” Damon joked to Interview magazine.

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They bonded over baseball and broke into movies

Both were passionate Red Sox fans and Little Leaguers; before he got the acting bug, Damon’s original ambition was to be a ballplayer. Meanwhile, Affleck’s mom knew a casting director, so he wound up doing a TV commercial, and then a movie, The Dark End of the Street, at age 13. The two first appeared in a film together in 1989 when they landed spots as extras (among thousands) in Field of Dreams, where Kevin Costner impressed them by taking time to chat with them.

When Damon was 10, Affleck defended him from a schoolyard bully

“I mouthed off to this kid,” Damon told Conan O’Brien. “He was like 6 foot 6, and I might have been 5-3 at the time, and I said something. This mountain of a guy came at me. … I was on the ground, he was above me, and I was like, This is gonna be bad. Ben Affleck tackled this dude off of me … literally at the risk of his own life. That was a big moment … like, This guy, he will put himself in a really bad spot for me. Like, This is a good friend to have.

When they finally made money in Hollywood, they spent it fast

The pair felt they had hit it big when they both got cast as jerks tormenting star Brendan Fraser in School Ties (1992). “It was one of the best experiences of my life,” Affleck told Entertainment Weekly. “We literally were [living] next to a dump and thought we were kings.” They put their money in a shared bank account. “We blew it all in a couple of months,” Affleck recalled. “We made $35,000 or $40,000 each and thought we were rich. And we were shocked later on to find out how much we owed in taxes. We were appalled: $15,000! What? But we rented this house on the beach in Venice and 800 people came and stayed with us and got drunk. Then we ran out of money and had to get an apartment. … We’d get thrown out of some places or we’d have to upgrade or downgrade, depending on who had money.”

spinner image Ben Affleck and Matt Damon in a scene from the film Good Will Hunting
Ben Affleck (left) and Matt Damon in "Good Will Hunting."
Miramax/Courtesy Everett Collection

Good Will Hunting reduced them to tears

On the first day of shooting the 1997 film they had spent years writing thousands of pages of drafts for, and then at last against all odds costarred in, both broke down and cried. “We might have cried for other reasons had we been able to see the whole future and understand the complexity of what we’d gotten ourselves into,” Damon told GQ.​

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After their big break, they paired up a few more times …  

The friends played fallen angels trying to scam their way back into heaven in Dogma (1999) and egomaniac actors filming an action-flick sequel to Good Will Hunting in Jay and Silent Bob Strike Back (2001). In one scene, Damon points a shotgun at a Harvard snob, shouting, “It’s hunting season!”​

… but mostly they avoided collaboration

“We fell prey to this idea that, ‘Well, if you don’t individuate your careers and do your own things, people will always associate you together, [and] that will be limiting,’ ” Affleck told The Hollywood Reporter. “That was advice we got.”​

Affleck became known for blockbusters, Damon for highbrow roles

Consider 1998. Affleck got $600,000 to star in the asteroid-menacing-Earth movie Armageddon, the year’s number one hit; Damon did Saving Private Ryan, the infinitely more prestigious number two hit. “People went, ‘Oh, well, Ben’s the big movie guy. And Matt’s the serious guy,’ ” Damon said when he interviewed Affleck for Entertainment Weekly. “But the fact was that we were [each] desperate to get another job, and I would’ve happily taken Armageddon. You would’ve happily taken Saving Private Ryan.”

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spinner image Ben Affleck and Matt Damon pose for a portrait at the Four Seasons Hotel in Los Angeles
Photo by: Ashley Landis/AP Photo

Moviemaking was more fun together than apart

When they reteamed to write 2021’s historical epic The Last Duel, Damon’s wife told him, “I haven’t heard you laugh like that in 15 years.” Growing older made the pair realize they should grow together again. “We came out of that experience going, ‘Why aren’t we doing this more often?’ And getting into your 50s, you just go, ‘If we don’t make it a priority, it’s just not going to happen,’ ” Damon told AP.

They’ve always had each other’s back — even when one does something foolish with it

When Affleck got a giant tattoo of a rising phoenix on his back, his ex, Garner, objected. “A phoenix rising from the ashes — am I the ashes in this scenario? I take umbrage. I refuse to be the ashes.” But old pal Damon told Trevor Noah, “It’s not one man’s job to tell another man what he can do to his back. You know, I support him in all of his artistic expression.”

They might not have made it without each other’s love

In their Entertainment Weekly interview, Affleck made it clear how much his friendship with Damon has meant to him. “I don’t know that [it] would’ve been possible for me alone, doing this job in this world without somebody I grew up with who I loved, who I knew loved me and had my back, who believed in me, and whom the popularity of my movies or what people said about me wasn’t going to change what they thought about me,” Affleck said. “This friendship has been essential and defining and so important to me in my life.”

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