Matt Damon and Ben Affleck’s First Big Payday Changed Everything
Matt Damon and Ben Affleck’s first major Hollywood paycheck for Good Will Hunting brought excitement—and a tough lesson about taxes. Their journey from struggling actors to industry icons is filled with hard-earned wisdom, discipline, and a string of hit collaborations.
When Matt Damon and Ben Affleck landed a $600,000 deal for their Good Will Hunting script, it marked a turning point in their careers. The Oscar- winning film not only brought Damon an extra $350,000 for his starring role, but also delivered a reality check neither of them saw coming. That first big check was a thrill, but it quickly became a crash course in financial responsibility.
Learning the Hard Way: Taxes and Hollywood Paychecks
During a recent appearance on The Howard Stern Show, the duo opened up about how quickly their windfall disappeared. Affleck admitted,
“Well, it turns out, Howard, you have to pay these things called taxes. Which I wasn’t quite as familiar with. I was like, ‘So, who gets half, again? Explain this to me?’”
Damon echoed the confusion, laughing as he recalled,
“It was a big wake-up call. Also, we were like, we understand this guy gets half, but wait—Who else gets half? What’s happening?!”
Despite the initial shock, both actors have since built impressive careers and fortunes, becoming two of Hollywood’s most respected names.
Good Will Hunting, released in 1997 and directed by Gus Van Sant, starred Robin Williams, Damon, Affleck, Stellan Skarsgård, and Minnie Driver. With a $10 million budget, the film grossed nearly $226 million worldwide and earned critical acclaim, scoring 8.3/10 on IMDb and a 97% Tomatometer rating. Today, you can stream it on Prime Video.
Choosing Roles: Damon’s Discipline and Affleck’s Lessons
Before their breakout, Affleck credits Damon for teaching him the value of being selective with roles, even when money was tight. On The Howard Stern Show, Affleck shared,
“To Matt’s credit, and I really learned this from him, I thought he was f***ing nuts. He’d be like, ‘I don’t think we should do that movie, ’ ‘I’m not gonna do that movie,’ ‘I don’t like it,’ or ‘I don’t want to audition for that.’ And imma be like, ‘You don’t have any money! We are broke, dude. What the f**k you talking about?’”
Damon, with a laugh, replied,
“One of us had to pay rent.”
Affleck admitted that, early on, he was more focused on taking any job that paid the bills.
“I will be like, ‘I’ll just do something that, you know, whatever will pay me. I wanna be able to make a living as an actor. ’ I thought he was kinda nuts, in that way.”
Over time, though, Affleck realized Damon’s approach was the smarter path, even if it was tough.
“Over time, I really learned a lot from that, and I realized that I was wrong. That the actual way to approach it is what Matt did. It’s just exceptionally difficult. Early on in my career, I did some movies I really liked, and I did some movies that, in retrospect, I’m not particularly proud of. But they were, like, somebody’s going to pay you $1 million, $2 million.”
Affleck’s Respect for Damon’s Work Ethic
Affleck has often praised Damon’s discipline and ability to turn down roles, even when they were struggling financially. He told Stern,
“It’s very counterintuitive, and I don’t know how you came to have that discipline so early on. You turned down movies that, I think, or even turned down the opportunity to audition for movies that 99.9% of other young actors wouldn’t have.”
Affleck recalled taking a role in the 1998 horror film Phantoms for $250,000, joking,
“I did this horror movie, a Dean Kuntz, sewer monster movie called Phantoms, because it was $250,000, and I thought I was gonna be set for life. [Speaking to Matt Damon:] You wouldn’t have done that movie. And that’s just the truth.”
Damon’s careful choices have paid off. As of 2025, his net worth stands at $170 million, outpacing Affleck’s $150 million. Their partnership, though, has led to a string of successful collaborations, including Field of Dreams (1989), The Last Duel (2021), Air (2023), Small Things Like These (2024), Unstoppable (2024), The Accountant 2 (2025), Kiss of the Spider Woman (2025), and the upcoming Netflix action- thriller The Rip, set for release in January 2026.
Good Will Hunting is currently available to stream on Prime Video.