The failed audition that mocked Matt Damon for an entire summer: “That could have been us”

Hollywood can often be a place of jealousy and resentment – while you might be 90% happy for your colleagues and their successes, there will always be a small part of you that slightly hates them for achieving something you couldn’t. Whether it be a brand partnership or a six-figure movie deal, the business of show business is an inherently competitive place, with the people of Hollywood being pitted against each other in a sometimes ruthless climb to the top, with the underdogs often slipping by the wayside.

But in an industry that changes rapidly, the people at the bottom can find their luck changing very quickly, sometimes being met with weirdly serendipitous moments that predict their looming spell of success. This was certainly the case for Matt Damon while starting out in the industry, with one role he lost out on that paved the way for another one.

Damon’s Hollywood journey is now an infamous tale, with the story of him and Ben Affleck’s screenplay for Good Will Hunting and their subsequent Oscar win becoming a classic anecdote of rags to riches. But while their story is one that seems to point towards sudden success, with the pair becoming the youngest duo to win the Oscar for ‘Best Original Screenplay, there were many years of invisible struggle that we didn’t see, with Damon describing their grafting behind the scenes and one opportunity they lost out on that haunted them forever.

While Robin Williams is a key part of Damon’s career, with the actor starring in Good Will Hunting and winning an Oscar for his part as the warm-hearted psychology professor, there was nearly an alternate course of history in which Williams first worked with Damon in 1989, with the young actor auditioning for a role in Dead Poets Society, another staple within Williams’ filmography.

The film made stars out of Robert Sean Leonard and Ethan Hawke, and while there were many young men needed for the film, Damon and Affleck unfortunately didn’t make the cut. When discussing this, Damon said, “Well, Dead Poets Society. Ben and I got called back on that.”

“When it came out, Ben and I worked at a movie theatre in Cambridge, Massachusetts, and the one movie they played all summer was Dead Poets Society. 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.’”

It might be a painful experience to see others succeed at something you failed at, but this didn’t deter the pair. Damon reflected, “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.” It’s an industry that can either make you or break you, and for Damon, this tough rejection only lit the fire to keep going, eventually working with Williams himself just a few years later in 1997.

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