You probably think Good Will Hunting was the start. It wasn't. Long before the Oscars, the Southie accents, and the "How do you like them apples?" bravado, two skinny kids from Cambridge were just trying to get a free seat at a baseball game.
Ben Affleck and Matt Damon first movie together wasn't a starring vehicle. It wasn't even a speaking role. In 1989, they were just two faces in a crowd of 3,000 extras at Fenway Park.
The movie was Field of Dreams.
Most people miss them because, frankly, they are basically invisible. They aren't the stars playing catch in the corn; they are "background atmosphere" during the scene where Kevin Costner and James Earl Jones attend a Red Sox game. If you blink, you’ve missed a decade of Hollywood history in the making.
The Fenway Park Hustle
Honestly, they didn't do it for the craft. They did it because they were obsessed with the Red Sox.
Matt Damon has admitted in interviews, specifically on the Dan Patrick Show, that the primary motivation for taking the gig was getting onto the hallowed turf of Fenway. They were teenagers—Matt was around 18 and Ben was about 16. At that age, you don’t care about "building a reel." You care about being near the Green Monster.
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They spent the day sitting in the stands, leaning in and out of frame, trying to look like genuine baseball fans. Kevin Costner actually remembered them later, or at least he says he did. He told Jimmy Kimmel that he noticed two guys who seemed "on fire" with enthusiasm. Whether he actually pegged them as future A-listers or just thought they were caffeinated kids is up for debate, but the legend stuck.
The Batting Practice Myth
There’s a hilarious bit of friction between the two regarding this day. Ben Affleck loves to tell the story of how Matt has "misremembered" his own life.
According to Ben, Matt eventually started telling people he took batting practice at Fenway during the shoot and hit a ball off the Wall. Ben’s take? "Matt, you're remembering yourself as Kevin Costner." In reality, they were just two kids in the bleachers hoping for a glimpse of greatness.
Moving Up: School Ties and "Chesty" Smith
If you’re looking for the first time they actually had lines in the same room, you have to fast forward to 1992.
School Ties is a heavy-hitter for "before they were famous" sightings. You’ve got Brendan Fraser as the lead, a young Chris O’Donnell, and of course, our duo. This is the first Ben Affleck and Matt Damon movie where they aren't just blurry shapes in the background.
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- Matt Damon played Charlie Dillon: The privileged, anti-Semitic antagonist. He was the "bad guy" before he became the world's most relatable genius.
- Ben Affleck played Chesty Smith: Yes, that was his character's name. Chesty. He was a supporting player, one of the guys in the dorm, but he had a presence.
They lived together in a "dump" in Lowell, Massachusetts during filming. Ben once described the experience as feeling like "kings" even though they were basically living next to a landfill. It was the grind. It was the "we’re actually doing it" phase of their lives.
The Indie Deep Cut: Glory Daze
Before the 1997 explosion, there was a weird little 1995 indie called Glory Daze.
This is a deep cut. Ben is the lead, playing a guy named Jack who is terrified of graduating college. Matt shows up in a tiny, non-speaking cameo as a former roommate named Edgar Pudwhacker.
It’s a bizarre footnote. It made almost no money at the box office—something like $15,000—but it showed that even when one was the star and the other was just "the guy in the back," they were a package deal. They were constantly pulling each other into projects.
Why We Keep Talking About These Early Years
We’re obsessed with the Ben Affleck and Matt Damon first movie connection because it defies the "lonely actor" trope. Hollywood is usually a story of backstabbing and solo climbing.
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These two? They were a collective. They shared a bank account. Seriously. They had a joint account to fund their trips to auditions in New York City. They’d hop on the "Eastern Shuttle" for $20, smoke cigarettes like "idiots" to look grown up, and head home to Cambridge to plan their next move.
When Good Will Hunting finally happened, it wasn't a stroke of luck. It was the result of a decade of being extras, playing bullies, and doing cameos in tiny indies.
What You Can Learn from the Duo
If you're looking for a takeaway from their early trajectory, it’s basically this:
- Lower your ego early. If you have to be an extra in Field of Dreams just to get on the field, do it.
- Find your "accountability partner." Having someone to share a bank account with (metaphorically or literally) makes the "no's" easier to swallow.
- Vary the roles. Matt played the villain in School Ties while Ben took the lead in Glory Daze. They didn't care about hierarchy; they cared about the work.
How to Watch the Origins
If you want to do a "Damon-Affleck Origins" marathon, don't start with the Oscars.
Start with Field of Dreams. Put it on 4K, get a magnifying glass, and look for the two teenagers in the Fenway stands. Then move to School Ties to see Matt's underrated chops as a villain. Finally, hunt down Glory Daze for the pure 90s nostalgia.
By the time you get to their 2026 project The Rip, or their recent collaboration in Air, you’ll realize that the chemistry isn't manufactured. It's built on 35 years of standing in the background together.
Go back and re-watch that Fenway scene in Field of Dreams tonight. Look for the kids who look like they’re just happy to be there. They had no idea they were about to change the industry.