Even Howard Stern Gasped At The Offer Ben Stiller Turned Down From Matt Damon And Ben Affleck Because Of One Condition

Fans can listen to Ben Stiller and Howard Stern together for hours. They took on an entertaining interview together, with Stiller revealing facts fans didn't know about. Among those reveals was turning down a major project alongside Matt Damon and Ben Affleck back in the late '90s. We'll reveal what that project was, and why Stiller turned it down. Even Howard Stern reacted in shock to what Ben turned down.

We'll also reveal the struggles Affleck and Damon faced making that said film. We'll conclude by taking a closer look at Damon and Affleck's working and off-camera relationship today, and how things evolved.

Ben Stiller Passed On Directing Good Will Hunting After Ben Affleck And Matt Damon Requested They Also Star In The Film

Back in 1997, Good Will Hunting made a huge splash, and one that wasn't expected. Off a budget of $10 million, the film was able to turn a profit of $225 million. The film also got lots of Oscar buzz, nominated for Best Picture and Best Director. The film won for Best Supporting Actor with Robin Williams, along with Best Original Screenplay for Affleck and Damon.

Gus Van Sant directed the film, but as it turns out, Ben Stiller was also in the mix early on. The actor admitted he was sent the script, but ended up passing on it early on because of that fact the writers of the script, Matt Damon and Benn Affleck were attached the star actors.

Stiller revealed, “I got sent it by my agent at the time. The first turn off was that these two guys were attached to it to act in it who wrote it. I was like, ‘What? Come on. I cast my own projects. Who are these guys?’” Ben recalled with a laugh. “So that was one that I was like, ‘Uh, I missed the boat.’”

Stern gasped at Stiller's reveal and the fact that he passed on the script. Nonetheless, Stiller admitted the timing just wasn't right. “Sometimes it’s [about] where you are in your life at that point. You go, ‘Okay, that was good, but I really couldn’t do it at that time,’” he concluded.

Despite missing out on the film, Stiller's career was just fine, and he continues to enjoy success today behind the camera thanks to Severance.

Both Matt Damon And Ben Affleck Admitted Good Will Hunting Was A Nightmare To Put Together

It changed their careers, but Ben Affleck and Matt Damon explained that writing Good Will Hunting almost ruined their friendship. Damon admitted the process of writing the film was a lengthy one.

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"I mean, I think Good Will Hunting took us so long. We were, like, unemployed, broke guys. It took us forever to write that screenplay."

"I think we wrote thousands and thousands of pages. I don't think we really knew what we were doing," he added. "I think that kind of put us off writing again, because we never thought we'd have the time."

However, it turned out to be a complete positive in the end, as it shaped both their careers. Damon said, "I think we found writing this that we actually kind of picked up structure over the last 25 years of kind of making movies, and so it went a lot faster."

The experience not only brought them closer together, but it also allowed for smoother working condition.

Matt Damon Revealed He Wastes No Time When Working With Ben Affleck, Even Today

Working together in the film Air, Matt Damon admitted he and Ben Affleck had no problem telling each other "you suck" when working together.

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“You can waste so much time by trying to be polite,” Damon said. “In the movie business, and in theater, they’ve developed a whole vocabulary for how to talk to somebody. And basically how to tell somebody they’re sucking, right? And, like, we can just say, ‘You suck.’”

On the personal side of things, Damon has added that his relationship with Affleck changed after his father's passing.

"After my dad passed in 2017 — and Ben was very, very close with him — it changed something in us, I think," Damon said. "You start to see the end game and you start to feel like, 'I want to make every second count. I don't want to fritter away time anymore.'"

Despite all the success and fame, it is great to see how close the two still are.