For those of you watching this week’s Off Camera episode, do not adjust your sets…that is me sitting across from Matt, humiliatingly dressed head to toe in a Red Sox uniform, having lost a bet to Matt when my beloved Dodgers lost in the world series for the second year in a row. And for those of you listening or reading, well, just imagine my shame.

For as long as Matt Damon can remember, he wanted to be an actor. So much so that he started his college essay with those very words. But before all the accolades and success, Matt was just a kid from Cambridge, MA who loved playing sports and watching movies. His chances of becoming a pro athlete came up short (both literally and figuratively), but he was determined to make a career out of acting after the seed was planted by an influential theater teacher and nurtured by his best friend and fellow cinephile Ben Affleck.

They had no road map for success, but Matt and Ben had an advantage over their teenage peers—they just wanted it more. They took the train from Boston to New York regularly for auditions, using money drawn from their communal acting bank account to cover expenses. Eventually, one of those auditions turned into a small part in the 1988 Julia Roberts feature Mystic Pizza, but Matt’s “big break” proved to be elusive. He auditioned for the eventual Academy Award winner Dead Poets Society but was rejected in favor of Ethan Hawke, and the cruel reality of the industry smacked him in the face when he was working at the local movie theater the following summer: “I went from the possibility of being in this great film to the guy tearing the movie ticket and watching people come out crying because they’re so moved. That’s the range in this business.”

So Matt and Ben decided to take fate into their own hands and write a great film that they could both star in. That was how Good Will Hunting and the acclaimed acting careers of Matt and Ben came into being. It’s been 20 years, and Matt’s career is still going strong.

As our first two-time guest, Matt joins Off Camera to talk about his acting mid-life crisis, the gamble that almost cost Matt and Ben Good Will Hunting, the invaluable wisdom he’s gained from directors, and why the Boston Red Sox and specifically Fenway Park carry so much significance for him.