Matt Damon’s career breakout came opposite Robin Williams in 1997’s Good Will Hunting, but years earlier Damon found himself falling just short of working with the late actor.

During a recent EW SiriusXM Town Hall interview, Damon was discussing what he learned early in his career while fighting for roles that he ended up not getting. When asked if there was one that was particularly heartbreaking to miss out on, he revealed, “Well, Dead Poets Society. Ben and I got called back on that.”

Not only did Damon and Affleck fail to get their first big break with roles in the Academy Award-nominated film — even though they did go on to win their own Best Original Screenplay Oscar together for Good Will Hunting — but the pain on missing out on it soon became much worse for the best friends and future collaborators.

“When it came out, Ben and I worked at a movie theater in Cambridge, Massachusetts, and the one movie they played all summer was Dead Poets Society,” laughed Damon. “And we had to sit there in our black pants, white shirt, maroon vest, black bow tie, sit there, tearing tickets, serving popcorn, and then watch people bawling their eyes out as they came out. And we’re like, ‘That could have been us.’”

A few months before the film’s 1989 release, Damon had already made his film debut with a one-line role in the Julia Roberts-led Mystic Pizza. In 1992, Damon and Affleck finally got their first key roles in another school-based film, School Ties.

The Jason Bourne star feels like the unsuccessful experiences helped shape both of their careers. “There are the experiences that they either crush you or they inure you to the realities of this business, and for us it made us more determined.”

See the clip above and watch more clips from the interview below.

Jason Bourne runs into theaters on Friday.

Dead Poets Society
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