VIDEO: Ben Affleck and Matt Damon Join the Stern Show Together for the First Time

Ben Affleck and Matt Damon, two of this generation’s most legendary leading men, treated Howard and his listeners to a rare joint appearance Monday morning in service of their eagerly anticipated new crime-thriller “The Rip,” out Friday on Netflix. The iconic actors, writers, and producing partners opened up about everything from the origins of their lifelong friendship — which began in Cambridge, Mass., around the time an 8-year-old Ben helped a 10-year-old Matt fight off a bully twice their size — to the four decades of success they’ve found in show business, beginning with their breakthrough Oscar win for “Good Will Hunting” and continuing on with dozens of acclaimed films and beloved franchises.

Before “Good Will Hunting” helped them become household names in 1997, Ben and Matt were living together in Los Angeles and doing whatever they could to get their careers off the ground. For as much as the struggling actors and die-hard Boston Red Sox fans had in common, they admit they took drastically different approaches to building their big-screen careers.

Affleck — like most up-and-comers — auditioned for almost every part that came his way. “I wanted to be able to make a living as an actor,” Ben told Howard.

“One of us had to pay rent,” laughed Matt, who revealed he was far more discerning when it came to the roles he pursued.

“I thought he was fucking nuts,” Ben laughed. “He’d be like, ‘I don’t want to do that movie. I don’t like it,’ … and I’d be like, ‘You don’t have any money! We’re broke, dude!’”

Over time, Affleck learned his friend was wise beyond his years. “I realized that I was wrong. The actual way to approach it is what Matt did — it’s just exceptionally difficult,” Ben said. “Early on in my career, I did some movies I really like, and I did some movies that, in retrospect, I’m not particularly proud of, but they were paying like a million dollars, two million dollars.”

“I don’t know how you came to have that discipline so early on,” he told Matt.

“Well, we had enough. We had the rent covered,” Damon responded.

“Still, you turned down movies — even turned down the opportunity to audition for movies — that 99.9 percent of other young actors wouldn’t have. I did this horror movie — a Dean Koontz sewer monster movie called ‘Phantoms’ — because it was 250 grand, and I thought I would be set for life, you know?” Ben continued. “You wouldn’t have done that movie — and that’s just the truth.”

As their wide-ranging conversation with Howard continued, Matt and Ben spoke candidly of the neighborhood they grew up in, their boyhood dreams of making it big in New York, the directors Ben learned the most from along the way, and how two of Damon’s most celebrated movies — “Saving Private Ryan” and “The Bourne Identity” — helped redefine their respective genres.

But through it all the conversation kept coming back to “Good Will Hunting,” the indie darling Damon first conceived of while studying at Harvard University. The duo, relative unknowns at the time, spent years polishing the script before getting it made into an Oscar-winning film.

And what of their memorable acceptance speech for Best Original Screenplay? Well, that one they improvised.

“We never, ever had a conversation between ourselves about what we would say,” Matt told Howard. “Honestly, it was like each of us knew deep down that, if we had that conversation and didn’t win, in 50 years we’d be at some bar in Boston going, ‘Can you fucking believe we wrote an Oscar speech? You jackass.’”

Looking back at that night almost 30 years later, Ben isn’t sure they made the right call. “Every time I see that [speech], I think, ‘What a noodge,’” he laughed. “I thanked Boston as a city, three times. Was that necessary?”

“I think you thanked Cuba Gooding Jr.,” Howard noted with a laugh.

“I did,” Ben said, adding, “It would’ve been smart to think about what I was going to say in front of the whole world.”

Pedro Pascal Was Cut From “The Adjustment Bureau”

Matt only had one line in Julia Roberts’ 1988 rom-com “Mystic Pizza,” but he looks back fondly at the movie-making experience. “I remember being so excited,” he said, explaining he spent three nights shooting the one big scene in which he appeared. “I knew I was where I wanted to be.”

Matt and Ben both agreed that being a day player in a movie is one of the hardest things for an actor to do. In many cases, however, even small roles can leave very big impressions.

“I did a movie with Emily Blunt called ‘The Adjustment Bureau,’ and there was this throwaway part with the maitre d’ — it got cut out of the movie — but I remember … this maitre d’ walked away, and they cut, and we both looked at each other and go, ‘That guy was really fucking good,’” Matt recalled.

“There was something incredibly interesting, and real, but natural,” he continued. “Years later, I found out it was Pedro Pascal. [He was] not even a day player with really anything else to do, just his presence — we both recognized it immediately.”

Matt’s Wife Thought Ben Was the “Cute One”

Matt and his wife Luciana Barroso have been happily married for over 20 years, but as Damon explained with a laugh on Monday, things might’ve gone differently had they met right after she first saw “Good Will Hunting.”

“After we’d been together for probably a few months, I met her best friend from high school, and it came out that the two of them went and saw “Good Will Hunting” together, and her best friend thought I was the cute one, and she thought Ben was the cute one,” Matt told Howard. “She admitted [it] to me. I’m like, ‘You got the wrong one?’”

Luciana is producing two of Ben’s 2026 films, “Animals,” which he’s also directing, and “The Rip.” “She’s a great producer and a really good friend,” Ben noted.

Howard was eager to talk more about “The Rip,” which both he and his wife Beth loved. He was especially impressed by Ben and Matt’s physical transformation into two hard-nosed narcotics officers.

“That’s part of the job. You gotta change your body somewhat, so that it’s just believable. As I’ve gotten older, that’s the hardest part of the job, frankly,” Affleck concluded. “Meeting with people in their lives is really interesting. The gym is only so interesting.”