Casey Affleck knows he’s not the first name filmmakers think of when it comes to comedy.

But after a decade away from acting in the genre (he last went for laughs back in 2011 opposite Eddie Murphy and Ben Stiller in Tower Heist), he knew that if he wanted to appear in a more lighthearted role, he was going to have to write a part for himself to play.

“That’s exactly what it was. I have done some comedies, but it’s been a while,” Affleck, 48, says in a video interview from Boston. “I’m not the first person people think of when they have a great comedy script, I guess. Those aren’t the jobs I get.”

So when Boston local Chuck MacLean (City on a Hill) approached the Oscar winner with the idea behind the comic crime caper The Instigators, Affleck jumped in feet first.

“Chuck had a good script and we spent a couple of years making it better,” Affleck says.

The film, which is now streaming on Apple TV+, casts Affleck opposite his longtime friend Matt Damon in a story about two bumbling robbers who are forced to go on the run from the police, dirty politicians and a vengeful crime boss after a heist doesn’t go as planned.

With a stacked supporting cast that includes Hong Chau, Alfred Molina, Michael Stuhlbarg, Ron Perlman, Toby Jones, Ving Rhames and Jack Harlow, the Doug Liman-directed movie is a throwback to the types of films Affleck and Damon grew up liking, with the two namechecking the 1988 action-comedy Midnight Run (which starred Robert De Niro and Charles Grodin) as an influence.

“I thought, if I’m going to sit down and work on a script, that’s the kind of film I want to make,” Affleck says.

“I don’t know why they don’t put him in more comedies. He’s so funny” Damon quips.

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Matt Damon and Casey Affleck star in the action-comedy ‘The Instigators.’Photo by Apple TV+

When Affleck approached him with the idea, Damon, 53, says he was immediately intrigued. The two have worked together many times over the years, including the Ocean’s Eleven trilogy, which also starred Brad Pitt and George Clooney, and two Christopher Nolan films Oppenheimer and Interstellar — where they didn’t share any scenes.

“I loved the characters that Casey created with Chuck,” Damon says. “It was unlike anything I had done and tonally it was fun, so I was in. It was fun to reunite with Doug (who directed Damon in The Bourne Identity more than 20 years ago), fun to reunite with Casey, and fun to put them together.”

Damon liked the idea so much that he pitched it to his pal and Casey’s brother Ben Affleck as a title they could release under their joint production company Artists Equity.

“It was everything I wanted it to be,” he says with a smile.

Matt and Ben
Oscar winners Matt Damon and Ben Affleck hold the awards they won for best original screenplay for the film ‘Good Will Hunting’ at the 70th Annual Academy Awards.Photo by Hal GARB /Getty Images

For his inspiration, Liman looked to the 1976 sports comedy The Bad News Bears.

“It’s a film that Ben, Matt and I all grew up with about a Little League baseball team that can’t do anything right. That was my starting point,” he says. “The heroes of this movie are not even the B team ⎯ they are the E or the F team.”

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Casey Affleck, director Doug Liman and Matt Damon share a laugh on the set of ‘The Instigators.’Photo by Apple TV+

Nearly 30 years after they first worked together on Chasing Amy and Good Will Hunting— the film that landed Damon an Oscar and catapulted him to worldwide fame — the two were eager to talk about their latest collaboration and trade jokes with one another. 

“I was paying this dude’s rent,” Damon says, talking about those early years. Affleck lets out a hearty chuckle in response. “Here we go again.”

My wife and I enjoyed this film a lot. The dog watched it with us and even one of the cats stuck around and that doesn’t always happen. Casey, why don’t people give you more comedies? I think you’re hilarious. I remember when you hosted Saturday Night Live, you were so funny.

AFFLECK: People always seem to be a little bit surprised when I’m in something funny. They think it’s a fluke. That’s the kind of thing people say to me. ‘Oh man, you were actually really funny on SNL.’ It’s the actually part that I hear.

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Matt Damon and Casey Affleck in a scene from ‘The Instigators,’ now streaming on Apple TV+.Photo by Apple TV+

Matt, how did you react to this story when Casey came and pitched it to you?

DAMON: I loved it. The script was still a work in progress when they brought it to me. But we immediately started talking about directors and Doug Liman was the first person we thought of. If you look at all his movies whether it’s Swingers, Go, Bourne, Mr. & Mrs. Smith, Edge of Tomorrow they’re all so unique. They’re all so different and a little bit off-kilter and that’s exactly what we needed … I’m glad to hear you had fun watching it.

AFFLECK: What did the cat like?

Well … they usually don’t sit on the couch when we’re watching a movie. So I assume they were enjoying it.

AFFLECK: When I had little kids, I would put on certain songs and it would put them to sleep. I don’t think it meant that they liked them. Maybe your cat was lulled by the sound of our voices.

I’ll have to put on one of the Ocean’s movies and see if they hang around to watch.

DAMON: They might just be fans of ours. That could be a thing … This could be our new metric. Instead of Rotten Tomatoes, maybe we’ll call you and see how the pets liked it.

Matt, it’s been a while since you’ve done a comedy. Downsizing had some humour, so this was refreshing to see again.

AFFLECK:Downsizing wasn’t supposed to be a comedy was it?

DAMON: It had some funny things.

AFFLECK: It did? Well, I know I saw it.

DAMON: (Laughs) This is the kind of love and support I get.

You two have known each other since you were kids. What’s the funniest thing you can tell me about one another?

DAMON: The funniest thing about Casey is that he will call you and have a four-hour conversation about a decision he’s trying to make and then hang up having gotten nowhere. You will have had an entirely circular conversation with him for two to four hours. Then I’ll call Ben and say, ‘God, I was just on the phone with your brother for three hours,’ and he’ll say, ‘Yeah, I was on the phone with him this morning for three hours.’ Casey has a Rolodex of people that he calls and has the same conversation with when he’s trying to make a decision about something.

AFFLECK: The funniest thing about Matt is that he’s a really moral, honest, reliable good person. But then he’ll go in a very public space like an interview at a press junket and lie his ass off.

We have spoken several times over the years, but I’ve never asked about the experience you both had on Good Will Hunting. When you were making it, did you know it was going to change the course of your lives?

DAMON: We hoped it was going to change our lives. We hoped we were going to be in a position where we would get consistent work. While it was filming, the scenes were going the way we were hoping they would go. It felt good. So we were guardedly optimistic … but there was no way to know. But Titanic came out at the same time, which was this historic thing. It was breaking (box office) records every weekend. We just sat behind it in second place and just (coasted) off the success of Titanic. So many people were at the movies that everybody in the movie business benefitted from that phenomenon. Good Will Hunting became really successful, but a large part of that was this cohort of other movies that were also playing at the time, particularly Titanic.

Good Will Hunting
Cole Hauser, Casey Affleck, Matt Damon and Ben Affleck in ‘Good Will Hunting.’Photo by Miramax

AFFLECK: Gus Van Sant was also a hot director and he’d just made two of his best movies. So there must have been some indication when he came on board to direct it that at the very least it was going to be given the chance to be seen.

DAMON: We felt great about the movie, but the only thing we can control is the movie we make. Rounders, which I released right after, was a box office bomb. Seven or eight years later, it finally made it into the black because people discovered it on home video. So you just don’t know. You can only make the best movie that you can and hope the movie gods are with you and the audience is going to show up. Our whole careers are dictated by the moviegoers. They have all of the control. It’s like a vote in an election. You get to keep your office if people keep showing up for you.

The Instigators is streaming now on Apple TV+

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