Casey Affleck, Ben Affleck and Matt Damon’s Unbreakable Bond: From Their First Oscars to Life as Hollywood Royalty

From students at Cambridge Rindge and Latin School in Massachusetts, to Hollywood stars with nine Oscar nominations among them, Casey Affleck, his brother Ben Affleck and Matt Damon have come far. And stayed close through it all.

In 1997, Damon and the elder Affleck’s film Good Will Hunting — which also starred Casey — propelled them to fame and their first walk on the Academy Awards stage. Now, 20 years later, Oscar continues to smile on them: Damon is a nominated producer on Best Picture contender Manchester By the Sea, which features an Oscar-nominated performance from Best Actor hopeful Casey Affleck. In 2013, Ben himself won an Oscar for producing Best Picture victor Argo.

Nearly 20 years ago, Damon and Ben were nominated for Best Original Screenplay for Good Will Hunting, bringing their mothers as their dates for the big night. Obviously giddy when they won the award, Damon — who was also nominated for Best Actor for his performance in the film — even quipped to a reporter that he wasn’t disappointed to lose out on that other race.

“I’ve never even been here before. I didn’t care!” Damon, then 27, said when asked which statuette he wanted more.

Meanwhile, then-25-year-old Ben didn’t let his brother Casey go unmentioned, calling him “brilliant” during his acceptance speech.

In fact, Ben and Damon made sure Casey had a role in the box-office juggernaut, which also starred Robin Williams in an Oscar-winning performance and followed a secret mathematics genius working as a janitor at MIT. Casey played Morgan O’Mally, a friend of Damon’s titular character.

The big night was only the beginning for the threesome. Films like Armageddon and Pearl Harbor followed for Ben, while Damon starred in Saving Private Ryan, The Talented Mr. Ripley, the Bourne franchise and Ocean’s Eleven, Twelve and Thirteen – with Casey.

Damon was nominated for an Oscar twice more before his nod this year as a producer on Best Picture contender Manchester By the Sea.

The friends have also collaborated offscreen, starting production company Pearl Street Films. They even oversaw the docu reality series Project Greenlight for four seasons – a show that followed first-time directors making a feature-length movie.

“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,” Damon told Entertainment Tonight last year of their tight connection.

Echoing his pal, Ben said of Damon to ET earlier this year, “I can’t tell you how valuable it is to have somebody who’s been through things with you, ups and downs, who knows what your life experience is like, who can identify with that.”

He added, “It’s an incredibly valuable friendship and it’s very precious and so is my friendship with my brother. I don’t know what I would do without those guys.”

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Casey’s big moment has come this year, as well, as the star of Manchester. He’s up for Best Actor – an honor he already nabbed at the 2017 Golden Globes. (Casey has been nominated for an Oscar before: He was in the running for Best Supporting Actor in 2008 for The Assassination of Jesse James by the Coward Robert Ford.)

His triumph in Manchester is in part due to his friendship with Damon, who had originally signed on to play Casey’s part, according to Variety, before focusing on his duties as a producer.

“I wasn’t interested in producing it for another actor, unless it was someone I grew up with and loved dearly,” Damon said of handing over the part. “I knew he would be able to do it in a way where I wouldn’t regret giving it to him. He’s one of the best actors I’ve ever met.”

Ben, for his part, couldn’t be more excited for Casey. During a recent interview, he noted that “it would be historically the first time brothers would win something separately” at the Academy Awards.

He joked further, “This will be the very first time someone would win an Oscar who didn’t brush his teeth from ages 10-14.”