Skip to main content

Ben Affleck and Matt Damon have remained close friends after nearly 30 years of Hollywood fame and fortune. Neither has been shy to talk about their humble beginnings. In the late nineties, the roommates wrote the screenplay for “Good Will Hunting” (1997) in their apartment in Eagle Rock. When the pair sold the script, Affleck says he was shocked at the lump sum they were offered. What’s more, they burned through the cash in about six months – and a lot of it was spent on Jeeps.

Affleck and Damon hailed from Cambridge, Massachusetts. They had decided to enter the film industry together, working in commercials and lesser-known projects for years in the late 1980s and early 1990s. At the time, Eagle Rock was cheap to rent in for LA standards. The pair even shared a bank account to help fund their careers as a team, as Affleck told Drew Barrymore on her talk show in 2023.

Affleck explained that he and Damon wrote and then sold “Good Will Hunting” for a clean $600,000. They split the sum, but after agent fees and taxes, they were left with about $110,000 each.

A black 1997 Jeep Grand Cherokee parked outside on blacktop in left front angle view
1997 Jeep Grand Cherokee | Bring a Trailer

“We each bought $55,000 Jeep Cherokees.”

In multiple interviews promoting the 2023 film “Air,” Affleck and Damon detail their first big purchase after selling the screenplay.

In an IMDb interview, they shared that they both wanted a hunter-green Jeep Grand Cherokee. “It was like the really dope, new truck at the time,” explained Affleck.

In 1997, the Jeep Grand Cherokee Laredo 4WD started at $25,545, and trims went up from there. They agreed to each buy one but didn’t want two of the same color. So, how did they decide who got the preferred green Grand Cherokee?

They flipped a coin, and the loser had to buy a black Jeep. “Who got the black one?” Marlon Wayans asked Damon. “Ben,” Damon quickly replied.

After buying the fraternal twin Jeeps, Affleck told Drew Barrymore that they rented a party house in the Hollywood Bowl that shaved $5,000 a month off their earnings. Within six months, he explained, they were pretty much broke again.

Of course, they ended up starring in “Good Will Hunting,” which became a Golden Globe and Oscar-winning film. The rest is his–(and his)–story.

Best in Tips, Tricks & Trends
Avatar photo
Editor-in-Chief

Sarah Kennedy

Sarah Kennedy joined the MotorBiscuit team as managing editor in 2021 and brings with her a bevy of automotive expertise. She’s an ASE-Certified Automotive Service Consultant and licensed car salesperson with over a decade of shop operations experience.

Sarah was the creator of “Shop Smarts” for MOTOR Magazine and was a contributor from 2013 to 2020. Her work earned her a Gold Medalist award from the American Society of Business Publication Editors in 2014 and Bronze Medalist awards from the International Automotive Media Competition in 2014 and 2015.

She has attended the Automotive Management Institute and earned her bachelor’s degree in English from The Ohio State University.