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Ever since Good Will Hunting, Matt Damon and Ben Affleck have been booking leading roles in big movies. A decade before their Oscar-winning film came out, they were struggling actors like anyone else. Damon says they even got close on a movie that became a cultural touchstone for young men everywhere. 

Matt Damon and Ben Affleck
L-R: Ben Affleck and Matt Damon | Jerritt Clark/Getty Images

Damon was a guest on Sam Jones’ Off Camera podcast on Oct. 8. It was his second visit to the show and he was the first ever returning guest. Damon told Jones the story of his and Affleck’s near miss in 1989.

Matt Damon and Ben Affleck took auditioning seriously 

As high schoolers in the ’80s Affleck and Damon were serious about their careers. They saved up their money from small jobs to go from Boston to New York for big auditions. 

Ben Affleck and Matt Damon
Ben Affleck and Matt Damon | Kevin Winter/Getty Images

“We had a joint bank account,” Damon told Jones. “It was a BayBanks card. The code was RiverP because we admired River Phoenix and we liked the choices that he made. So the bank card, RiverP was how you access it. We had a few hundred bucks in there whatever we made, local commercials, local voiceovers, any job we could get, we’d put the money in the account. That account was only for trips to New York for him and me, or video games after school.”

The ’80s classic Ben Affleck and Matt Damon auditioned for 

Here it is. By the time this audition came around, Damon and Affleck didn’t quite book it, but they were competing in the big leagues. 

“As you gain more experience auditioning, you get better at it and start to get feedback,” Damon said. “A great example being Dead Poets Society. Ben and I got close on that. We both auditioned, we both got called back. We read that and I was like this is a f*cking amazing movie. I was probably 17 or 18. It was like oh my God and it’s Robin Williams, this movie is incredible.”

Losing ‘Dead Poets Society’ was another valuable lesson

Dead Poets Society starred Williams as an inspirational English teacher at an all boys school. When Ethan Hawke and Robert Sean Leonard won the roles of his students, Damon experienced Dead Poets Society from the outside.

Dead Poets Society
Dead Poets Society | François Duhamel/Sygma/Sygma via Getty Images

We didn’t get it. We ended up having the summer job of working at the Janus theater in Harvard Square which doesn’t exist anymore. It played one f*cking movie the entire summer and it was Dead Poets Society. So you go from the possibility of being in the movie to the guy tearing the ticket and watching people come out crying because they’re so moved and watching Ethan Hawke f*cking get nominated for an Academy Award. Wow, that’s the range of possibility for you if you go into that business.”

Matt Damon, Off Camera with Sam Jones, 10/8/2020

‘Dead Poets Society’ was still a good experience for Matt Damon

Damon looks back at missing out on Dead Poets Society and sees that getting close was enough to reassure him of his career path.

Matt Damon
Matt Damon | Emma McIntyre/Getty Images for SiriusXM
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“But having said that, we did get called back,” Damon said. “So the business was telling us, ‘Hey, it didn’t work out this time but you’re doing some things right.’ The business is kind of telling you keep trying, keep plugging away and then you need to get extraordinarily lucky.”