Damon and Affleck's $600K Good Will Hunting Payday Taught Harsh Tax Lesson
The childhood friends thought they'd struck gold with their first major Hollywood payday, but Uncle Sam had other plans that left them scratching their heads about where half their money went.
Matt Damon and Ben Affleck thought they'd hit the jackpot when they pocketed $600,000 for selling their Good Will Hunting script back in the late '90s. Damon pulled in another $350,000 for starring in the Oscar-winning drama. For two struggling actors, this felt like winning the lottery.
But reality hit hard when tax season rolled around. The duo recently appeared on The Howard Stern Show, where they opened up about their rude awakening to the world of federal taxes.
The Tax Reality Check That Changed Everything
Affleck admitted he was completely blindsided by the tax implications of their windfall. "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?'" he confessed during the interview.
Damon echoed his friend's confusion with a laugh. "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?!" The pair genuinely couldn't grasp how much of their earnings would disappear to various government entities.
Despite the shock, both actors have built impressive careers since then. Their combined net worth now reaches well into the hundreds of millions.
Affleck Credits Damon's Selective Approach to Roles
During the same interview, Affleck praised his longtime friend for being incredibly picky about projects from the start. This selectivity often baffled Affleck, who was more focused on paying bills than artistic integrity.
"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?'" Affleck recalled.
Affleck took a different approach early on. "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." Damon jokingly defended himself: "One of us had to pay rent."
Learning the Hard Way About Quality Over Quantity
Affleck eventually realized his friend's strategy was smarter. "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."
He cited his 1998 horror film Phantoms as an example of choosing money over quality. "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. You wouldn't have done that movie. And that's just the truth," he told Damon.
The selective approach seems to have paid off for Damon, whose current net worth of $170 million edges out Affleck's $150 million. Both continue collaborating on projects through their production companies, with their latest venture being the upcoming Netflix thriller The Rip, set for release in January 2026.