Matt Damon and Ben Affleck have spent more than two decades in Hollywood. Their latest collaboration, The Rip, offers a glimpse into how their shared history informs their craft.

“It’s about two old friends who suddenly can’t trust each other,” Damon told Krista Smith on Skip Intro. “People know us as friends, and so we kind of carry that baggage into the roles.” That interplay between real-life camaraderie and on-screen tension has long been a hallmark of their work, dating back to the breakthrough that launched both of their careers.

In the late 1990s, the pair earned an Oscar for Best Original Screenplay for Good Will Hunting. Affleck, still the youngest winner in that category, shares the spotlight with Damon. “I like to say we’re the two youngest,” Damon said. But the film’s success came from a deeper realization: to secure meaningful roles, they would need to create their own opportunities.

“It was actually the movie Primal Fear that was kind of our epiphany,” Damon said. “I got a dialect coach with money I barely had. I really worked hard on this audition, and Edward Norton got it. He was terrific in the movie, [but] that was when Ben and I went, ‘Well, we have to just write this thing. That’s the only way we're going to get good roles.’”

Since then, Damon’s career has been defined by versatility: the relentless Jason Bourne, the quick-handed Linus Caldwell, the stranded astronaut Mark Watney and now, Lieutenant Dane Dumars in The Rip. Preparing for the role, Damon shadowed Miami police officers to capture their dynamics authentically. “We went and did ride-alongs with Chris Casiano, the character who my character’s based on,” he said. “You want to try to get that feeling. There’s a certain way these guys hang out together.”

In the film, Dumars, Detective Sergeant J.D. Byrne (Affleck), and their narcotics team find themselves testing the limits of loyalty after uncovering $20 million in cartel cash. “Catalina Sandino Moreno’s character says it at one point: ‘I get 80 grand a year after taxes, and I get shot at, I get spit on, and your own department doesn’t trust you,’” Damon said. “It’s about, basically, how strong your ethical framework is.”

The Rip highlights not just the tension of crime and duty but the enduring creative synergy between Damon and Affleck — a partnership that began with a self-written script and continues to evolve with each project. Beyond the film, Damon also discussed his role as CCO and co-founder of Artists Equity and teased his upcoming lead in Christopher Nolan’s The Odyssey on Skip Intro, proving that his career, much like his friendship with Affleck, is one built on collaboration, ambition and a willingness to take risks.