The Real Reason Matt Damon Loves Working With Casey Affleck

Matt Damon frequently collaborates with his childhood friend Ben Affleck. But now, for the first time in 22 years, he’s co-headlining a movie with his other best friend: Ben’s younger brother and best actor Oscar winner Casey Affleck, in the action-comedy caper The Instigators.

“Casey is one of the most creatively tenacious people that I have ever met,” says Damon in a joint interview with Affleck. “He really cares and thinks deeply about every single thing he says and does on the screen. He’s meticulous about his preparation and deeply reflective about it. I even accuse him of overthinking sometimes because he cares so much.”

The Instigators marks the pair’s first major acting collaboration since the 2002 indie drama Gerry. Though both actors appeared in the Ocean’s trilogy, they barely interacted with one another onscreen. They also both appeared in last year’s Oppenheimer, but had no scenes together. “We always look for ways to work together in any capacity we can,” Damon says. “We have been in each other’s lives for 43 years, so any excuse to try to find something that we can do together, we’ll jump on it. It’s just very hard to find material that would support us being together onscreen.”

The film, out in select theaters on Friday before its August 9 wide release on Apple TV+, brought the longtime friends back to their native Boston. It centers on a broke and debt-ridden former marine (played by Damon) who is depressed over not being able to provide for his teenage son, and partners with a wisecracking ex-con (Affleck) to rob a corrupt politician. But when the heist goes wrong, the two find themselves pursued by police, dishonest bureaucrats, and vengeful crime bosses. Affleck co-wrote the script with Chuck MacLean, the creator of the Showtime series City on a Hill.

“I wanted to do something that was fun,” says Affleck, known for intense performances in dramas including Gone Baby Gone and his Oscar-winning performance in Manchester by the Sea. “I recently had done a bunch of darker, smaller movies, and wanted to do something that was kind of commercial and big again, and that was funny.”

Affleck sent the script to Damon’s wife, Luciana, who was enthusiastic about the story and urged Damon to read it. “I rarely find scripts that make me laugh so much, and it was one of the reasons why I really wanted to do this,” says Damon. “The biggest appeal for me was Casey, though.” Once Damon was onboard, Affleck knew he would elevate the screenplay. “There’s no one better than Matt,” he says.

Working with friends or family in any capacity can be tricky. But for Damon, that closeness means he can be brutally honest with his feedback. “It’s one of the reasons why I love working with Casey and why I love working with Ben, because we have this shared trust and respect that just isn’t ever in question,” he says. “So it allows you to be entirely undiplomatic when you’re having these creative conversations. We know each other well enough that our feelings and our egos don’t really get involved.”

Damon remembers that when he and Ben started to write Good Will Hunting, Ben said to him, “Judge me for how good my good ideas are, and not how bad my bad ideas are.”

“That was the most profound thing, because that is exactly what you need in a partnership,” says Damon. “You need to get every idea out. And if you’re afraid that somebody is going to think less of you because of your bad ideas, that’s really going to slow everything up. You get there a lot faster if you’re not worried about people’s feelings. So, in other words, we talk a lot of shit to each other.”

Their shit-talking translates onto the screen. Affleck and Damon play reluctant crime partners who can’t do anything right. They argue constantly, but must put aside their differences to work together. Acting out those bickering scenes came naturally to both Affleck and Damon. “Bouncing back and forth with one another, that’s stuff we have done for years,” says Damon. “That’s just kind of the way we joke around. So that felt very natural for both of us.”

Affleck grew up alongside Damon throughout their teen years in Cambridge, Massachusetts, and shared the screen with both Damon and Ben in Good Will Hunting. That movie’s origin story is now Hollywood lore: It’s a script penned by two young friends from Boston who decided that the only way to break through was to write their own film.

“It’s strange when you watch somebody grow up who’s a little bit younger than you,” says Damon, who is five years older than Casey. “When I was a teenager, he was an adolescent. He was always around, and he was there with me into my 20s. Then suddenly I woke up and realized that this kid was one of the best actors I had ever seen. It all happened in front of my eyes. I learn a lot from him every time I work with him. He pushes me really hard, and I love that.”

Affleck credits his high school drama teacher Gerry Speca for instilling a strong work ethic into him, Ben, and Damon. “He had a really big impact on all of us, and Matt is a good example where that can take you. I’ve never seen him being phony in anything. He busts his ass, he makes the projects overall better, and not just his own part.”

Damon is currently committed to growing the production company that he founded with Ben, Artists Equity, which has pioneered a model that shares profits not only among directors, producers and actors, but also crew members. Affleck, meanwhile, is focused on continuing to act and write with a renewed outlook.

“I’ve been really liking working on movies again, especially working with people who I both respect and also love,” he says. “In the last 39 years that I have been working, I’ve climbed pretty high on the mountain and got knocked down. I’ve climbed half way up and been knocked down, and I’ve gotten a quarter the way up and got lost and turned around and came back down on my own. It’s been a lot of ups and downs, and I realized it’s not so much getting anywhere on the mountain that I care about, but now, it’s about who else is climbing with me. I really want to enjoy that a little bit more.”