From Childhood Friends to Oscar Winners: A Look Back at Matt Damon and Ben Affleck's Hollywood Bromance

Too Cool for School

Damon and Affleck met as young boys growing up in Boston. They graduated from the same high school — Affleck in 1994 and Damon in 1992. Damon's brother, Kyle, told PEOPLE that the pair "weren't considered cool kids." In fact, "They were drama geeks."

The pair started auditioning together and eventually appeared in their first film, School Ties, in 1992. Can you spot them in this photo?

Fast Friends

Affleck said of their instant bond, "Matt gave acting a framework, an integration into the social hierarchy at school. 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. None of the other kids knew what it was I did, how it worked, or anything."

Affleck said, "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. Soon both of us are doing it."

Big Break

In 1996, the pair wrote the their breakout hit Good Will Hunting together, and naturally played best friends in the film.

Golden Guys

The pair dominated the awards circuit in 1998, winning the Golden Globe for their original screenplay.

And the Academy Award Goes to...

They became Oscar winners, too, when they won Best Original Screenplay in 1998.

Their adorable joint speech started with Affleck saying, "Ha! I just said to Matt that losing would suck and winning would be really scary, and it's really, really scary," and included the pair reminding each other who to thank and shouting them out.

Sharing the Screen (Again)

The following year, the pair appeared alongside each other in the 1999 comedy Dogma.

Red Carpet Ready

Name a more iconic red carpet friendship, we'll wait.

Give Them the Greenlight

Project Greenlight, that is. The pair teamed up again, this time to produce the HBO documentary series Project Greenlight, which focused on first-time filmmakers. The docuseries ran from 2001 to 2005, and then again in 2015.

Know When to Hold 'Em

Sometimes you just need your good luck charm — like, oh, Matt Damon — while you're betting big at a charity poker tournament, as Affleck did here in 2012.

Hollywood's Greatest Bromance

In 2010, Damon received the 24th American Cinematheque Award, and Affleck and his then-wife Jennifer Garner were there to support him, with Garner calling them "the actual prototype for the great Hollywood bromance."

Bonded For Life

Damon told Entertainment Tonight of their friendship, "I've known him for 35 years, and we grew up together. 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."

Producing Partners

Together, the pair started their own production company, Pearl Street productions, and continue to produce films together.

Guys of the Decade

In 2016, they were awarded the Guys of the Decade award by Spike TV's Guy's Choice Awards. An honor that is clearly well deserved.

Back Where It All Began

The duo presented the award for Best Adapted Screenplay together at the 2017 Oscars.

Boston Buds

And of course, there's little more important to the pair than their love of the Boston Red Sox.

What's Next?

At the 2019 Toronto International Film Festival, Damon told Extra that the pair are linking up again for The Last Duel.

Damon told the outlet, "We wrote for the first time in 25 years with Nicole Holofcener, who is a hero of ours — amazing writer, she's great. The three of us wrote this thing, so hopefully we will shoot it next year."

All Love

With a friendship as longstanding as theirs, its no surprise that their families have meshed as well. When it was time to attend the premiere of The Last Duel in New York City, Affleck, Damon and his wife Luciana had a laugh on the red carpet.

Reunited and It Feels So Good

In 2023, the two teamed up once again for the film Air which premiered at the SXSW festival. Affleck directed and starred in the film as Phil Knight alongside Damon as Sonny Vaccaro.

Dapper Dudes

Affleck and Damon were dressed to the nines as they presented together at the 2024 Golden Globes.

Suited Up

In an ode to their Boston roots, Affleck and Damon joined Patriots legend Tom Brady to create a trio of DunKings for an epic Super Bowl commercial in 2024.