Matt Damon and Ben Affleck’s First Big Payday: A Reality Check
Matt Damon and Ben Affleck’s first major script sale brought excitement and a hefty cheque, but what followed was a lesson neither expected. Discover what really happened after their Good Will Hunting breakthrough.
Back in the late '90s, Matt Damon and Ben Affleck were over the moon when they landed a $600,000 deal for their Good Will Hunting script. For two young blokes just starting out, it felt like they'd hit the jackpot. Damon even pocketed an extra $350,000 for his role in the film. But the euphoria didn’t last long, as the pair soon found themselves grappling with the realities of tax and money management.
Appearing on The Howard Stern Show, the duo looked back on that windfall. Stern, never one to shy away from a cheeky question, asked how they managed to burn through such a sizeable sum. Affleck admitted the thrill of the cheque was quickly dampened by the taxman’s cut.
“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, laughing, echoed the confusion,
“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 lesson was clear: even a big payday can shrink fast once everyone takes their slice.
Choosing Roles: Quality Over Quick Cash
That early experience wasn’t the only eye-opener for Affleck. He credits Damon for teaching him to be choosy about roles, even when they were both skint. On the same show, Affleck recalled how Damon would turn down projects he didn’t rate, even if it meant missing out on a paycheque.
“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 film,’ ‘I’m not gonna do that film,’ ‘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 his trademark dry wit, replied, “
One of us had to pay rent.
”
Affleck admitted he was more likely to take whatever came his way, just to keep the lights 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.”
Over time, though, Affleck realised Damon’s approach paid off in the long run.
“Over time, I really learned a lot from that, and I realised 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 films I really liked, and I did some films that, in retrospect, I’m not particularly proud of. But they were, like, somebody’s going to pay you $1 million, $2 million.”
Discipline and Regrets: Lessons from the Early Days
Affleck couldn’t help but praise Damon’s discipline, especially when they were both doing it tough. Even when Damon joked, “
Well, we had enough. We had the rent covered
,” Affleck was quick to point out how rare that kind of self-control was.
“It’s very counterintuitive, and I don’t know how you came to have that discipline so early on. You turned down films that, I think, or even turned down the opportunity to audition for films that 99.9% of other young actors wouldn’t have.”
Affleck shared a story about taking a role in the 1998 horror flick Phantoms, which didn’t exactly win over the critics but did pay him a tidy $250,000.
“I did this horror film, a Dean Kuntz, sewer monster film 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 film. And that’s just the truth.”
Damon’s pickiness, it seems, has paid off—he’s now worth about $20 million more than Affleck, with a net worth of $170 million compared to Affleck’s $150 million.
Collaborations and Ongoing Success
Despite their different approaches, the two have managed to work together on a string of projects over the years. From Field of Dreams in 1989 to The Last Duel, Air, and their much-hyped upcoming Netflix thriller The Rip, their partnership has stood the test of time. They’ve also teamed up on Small Things Like These, Unstoppable, The Accountant 2, and Kiss of the Spider Woman, with most of these recent projects produced through their joint venture, Artists Equity.
For those keen to revisit where it all began, Good Will Hunting is currently streaming on Prime Video.