In a recent appearance on The Drew Barrymore Show, Affleck explained that he and Damon believed they were “rich for life” after selling the screenplay for $600,000.
However, after taxes and the purchase of Jeep Cherokees and a $5,000-a-month rental party house, the pair broke within six months.
Despite this setback, both actors achieved A-list status in Hollywood.
Early Days in Hollywood
During the interview, Affleck reflected on his early days in Hollywood, when he and Damon were struggling actors trying to make it big.
He explained that they shared a bank account into their 20s and would work odd jobs, such as extra work or Burger King commercials, to pay for train tickets to New York for auditions.
He noted that starting in the entertainment industry could be a lonely experience but that their friendship helped them feel less alone.
In a March interview with the Hollywood Reporter, Affleck explained why he mostly avoided working with Damon for years after Good Will Hunting.
He said they fell prey to the idea that if they didn’t individuate their careers and do their things, people would always associate them together, which could be limiting.
They did appear in a handful of films together over the years and co-created the HBO filmmaking series Project Greenlight.
However, after Good Will Hunting, they didn’t collaborate for quite some time until they appeared together in Ridley Scott’s The Last Duel in 2021.
Affleck explained that after achieving success with Good Will Hunting, it was challenging to let go of the hand-to-mouth mentality they had as actors.
He said they took jobs where they would be paid a lot of money because the phone could stop ringing anytime.
As both actors grew up modestly, it was almost irresponsible to turn down high-paying jobs.
New Production Company
In November, Affleck and Damon launched their new production company, Artists Equity.
Affleck reflected on their friendship of almost 40 years, saying that he trusts and loves Damon and knows Damon has integrity.
He said that failure is hard in the entertainment industry and success is confusing, and having a friendship as a touchstone over the years has been meaningful.