Matt Damon Reveals He and Ben Affleck Were Broke After Winning Their Oscar

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Long before Matt Damon became a star in Christopher Nolan’s ‘The Odyssey’ or established his own production company, he was a struggling actor who experienced a significant turning point thanks to a screenplay he co-wrote with his childhood friend Ben Affleck. This script would ultimately transform their lives, and years later, Damon still shares the more challenging aspects of what transpired soon after their success.

‘Good Will Hunting’ catapulted Damon and Affleck to fame in 1997, earning them the Academy Award for Best Original Screenplay the following year, while also securing Damon a Best Actor nomination for his lead role. It was a dream scenario for any actor, a financial windfall that seemed to guarantee their futures.

However, that wasn’t the case, at least not right away. Matt Damon disclosed that he and Ben Affleck found themselves broke within about a year of selling the ‘Good Will Hunting’ screenplay for $600,000 during an appearance on the “New Heights” podcast hosted by Jason and Travis Kelce. He explained that after taxes, agent fees, and legal expenses took a significant bite out of their earnings, the harsh realities of Hollywood’s financial system hit them harder than they had anticipated.

Damon laid out the financial details clearly, mentioning that after splitting the sale, they were shocked to see their earnings dwindle once professional fees and taxes were deducted. “We sold the screenplay for $600,000, which was just… so much more money than either of us had ever considered,” he shared, admitting that they each ended up with less than $150,000 after all was said and done.

Affleck has recounted a similar story, providing an even more detailed account of where the money went. He remembered that after the $600,000 sale was divided and reduced by agent fees and taxes, they each purchased a $55,000 Jeep Grand Cherokee and opted to rent a $5,000-a-month “party house” near the Hollywood Bowl, a choice that left them financially strained within six months.

Screenshot 2026 08 06 at 13 47 49 Good Will Hunting Rotten Tomatoes

This early financial shock seems to have influenced how Damon and Affleck approach filmmaking today. Damon linked their past experience to the decisions made at Artists Equity, the production company he co-founded with Affleck, emphasizing their commitment to securing reversion rights on their projects rather than settling for flat paydays that offer little long-term benefit.

He specifically mentioned Affleck’s experience with ‘The Town’, noting that although the film generated significant revenue over the years, Affleck saw minimal profit at the time despite his roles as writer, director, and star. Damon suggested that this kind of imbalance is precisely what their current studio model aims to prevent for future collaborators.

Despite the initial financial difficulties, both actors’ careers ultimately thrived, with Damon and Affleck becoming two of Hollywood’s most bankable stars over the years. Damon is currently enjoying significant attention for his role as Odysseus in ‘The Odyssey’, which has emerged as one of the year’s top box office hits.

Reflecting on how close they came to squandering their big break, it serves as a reminder that even Hollywood’s most successful stories often lack a straightforward guide.

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