Matt Damon and Ben Affleck’s First Big Payday: A Costly Lesson

Matt Damon and Ben Affleck, long-time friends and collaborators, found themselves in uncharted territory when they landed a $600,000 deal for the script of Good Will Hunting. The film, which would go on to win an Oscar and see Damon pocket an extra $350,000 for his role, marked a turning point in their careers. Yet, the windfall came with a sting neither had anticipated: the taxman’s share.

Learning the Hard Way: The Taxman Cometh

Appearing on The Howard Stern Show, the pair recounted the moment their excitement was tempered by the realities of taxation. 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, equally bemused, added,

“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 confusion was palpable, but the lesson stuck. Both have since navigated the industry with a keener eye on the bottom line, and their fortunes have grown accordingly.

Choosing Roles: Quality Over Quick Cash

Before their breakthrough, Affleck credits Damon for instilling a sense of discernment when it came to selecting roles. Affleck recalled,

“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 wry smile, quipped,

“One of us had to pay rent.”

Affleck, reflecting on his own choices, admitted,

“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.”

The pair’s differing approaches to work in their early days have become something of a running joke between them, but the respect is mutual.

Discipline and Regrets: Affleck’s Perspective

Affleck has never shied away from acknowledging Damon’s discipline. During the same interview, he remarked,

“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.”

He cited his own experience with the 1998 horror flick Phantoms, which, while not a critical darling, did pay the bills.

“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 selectiveness, it seems, has paid off handsomely, with his net worth now outstripping Affleck’s by a fair margin.

Collaborations and Ongoing Success

The duo’s professional partnership has yielded a string of notable projects, from their uncredited appearance in Field of Dreams to more recent ventures like The Last Duel, Air, and the much-anticipated The Rip. Their joint efforts have spanned genres and platforms, with both taking on roles as writers, producers, and actors. The list of their collaborations continues to grow, a testament to their enduring creative chemistry and shared ambition.

For those keen to revisit where it all began, Good Will Hunting is currently available to stream on Prime Video.