In celebration of the actor and his many accomplishments, we dug into our archives and found the first time ET interviewed a baby-faced Ben -- at the red carpet premiere for Chasing Amy back in 1997, where he told us what it was like to kiss Jason Lee in the film.
"I'm not homophobic," he said then. "I just... I guess I am more than I thought, in that, it was just difficult for me you know? And I didn’t think it would be. I really backed down from it in a way. I really could have done more of a committed job."
Even years later, Ben's still apologizing for not being able to get over his own issues and just kiss his fellow actor. While promoting Argo in 2012, he told The New York Times, "I just blew it… It was not my proudest moment."
Ben was just 25 years old when he starred in the Kevin Smith romantic comedy. He played Holden, a comic book artist who meets and falls for Alyssa (Joey Lauren Adams) – who's into him, but primarily dates women. To add more challenges to filming, Ben had to shoot love scenes with Adams, who was director Smith's then-girlfriend, though he did his best to brush off the awkward.
"You just torture him you know what I mean?" he said, "I get to tweak Kevin, it's fun."
Less than a year later, Ben and best friend Matt Damon would be launched into mainstream fame with the film they co-wrote, Good Will Hunting, but at the time he was relatively unknown.
Check out the video above to see what Ben (in his fashionable leather coat) had to say about the hurdles he crossed while shooting.