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

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.

​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.”