Casey Affleck Is Taking Risks And Taking Names With His Latest Film, “The Instigators”

BY LAURA SCHREFFLER

PHOTOGRAPHY BRIAN BOWEN SMITH

STYLING ERIN MCSHERRY

GROOMING MELANIE HUGHES-WEAVER

SHOT ON LOCATION AT DOWNTOWN L.A. PROPER  

Casey Affleck has a hidden talent — one that, soon, will become visible to all. The Oscar winner, who is, arguably, one of the best dramatic actors of our time, is funny. Surprisingly, laugh out loud, roll on the floor, knee-slappingly funny. Even more surprising: he didn’t know that he could be… until he tried, that is, with his upcoming effort, The Instigators.

“I thought I had done comedies in the past. I would mention them to people, and they would say, like, ‘That’s not a comedy,’” the 48-year-old star confides from his LA home. “So, going into it, I was feeling a little bit insecure, like maybe my idea of funny is so different from other people’s that it doesn’t even register as an effort to be funny; maybe people just think that it’s a tragedy or something.”

So, which of his movies does he believe to be comedies? In an extremely serious tone, he references some of his most dramatic films. [Proof, methinks, of how funny he actually is.] He quips, “I thought Gerry [his 2002 drama co-starring Matt Damon, a.k.a. one of Gus Van Sant’s “Death Trilogy” films] was funny, but most people were like, ‘This was the most boring drama we’ve ever seen.’ I thought I’m Still Here [his 2010 mockumentary musical parody co-starring Joaquin Phoenix] was a comedy. Clearly, no one else did. I also thought there was a lot of funny stuff in a movie I directed called Light of My Life [his 2019 post-apocalyptic film involving a plague that wipes out most of the female population], but I never heard anyone laugh at any of the screenings.” He pauses. “I don’t know — maybe some of them are funny just because no one thought it would be a good idea to make them.”

He smiles, knowing full well that his self-deprecating schtick actually is funny. But when it comes to self-doubt, he isn’t joking: that was all true.

“With [The Instigators], I thought, I’m not sure this is going to work. And then it does work,” he admits.

And thank God for that, because this is a triple labor of love for Affleck, who co-wrote the script with Chuck MacLean, co-starred with Matt Damon, and co-produced alongside Damon and brother Ben’s production company, Artists Equity. In the Doug Liman-directed Apple Original film, a heist comedy that will make its global premiere on Apple TV+ August 9, Affleck plays ex-con Cobby, a Boston-based criminal with a smart mouth, the comedic foil to Damon’s straight-laced former military, desperate father-with-nothing-to-lose Rory. They are reluctant partners, thrown together to rob a corrupt politician’s ill-gained earnings. A botched robbery causes the two thieves to go on the run, pursued not only by police, but also by backward bureaucrats and vengeful crime bosses. With Rory’s therapist (Hong Chau) as their ‘hostage’, they work together to evade capture.

Now, Affleck is back to being self-deprecating as to why he thinks the film truly does work. “I don’t think that’s necessarily because of anything I did so much, but mostly because of the way it’s cut. Not to take anything away from Matt, but I think the dynamic between me, him, and Hong —and how well it really plays out — is really because of how good Doug is with shooting comedies, all the way from Swingers to Go. Even when he does movies like [the 2014 science fiction film] Edge of Tomorrow, there’s comedy in it. He always finds a way to make things funny.”

Yet, it was not Liman, Damon’s director in 2002’s The Bourne Identity, but Damon himself who Affleck initially tapped to direct the project. He had set out with the idea of wanting to write a buddy comedy, but wasn’t confident in his abilities to do so, so unearthed an old script courtesy of MacLean that was sitting on the shelf gathering dust. He spent about a year-and-a-half rewriting it, slowly but surely reworking the content while shooting other projects. And then, he shared it with Damon.

“I wanted him to direct it, because I thought he’d be a great director, but he had just never done it,” Affleck confides. “Periodically, I send him scripts, saying, ‘You should direct this.’ And consistently, he says, ‘no.’ Personally, I think he’s waited for so long to do it that he feels like he has to pick something perfect. And I keep telling him that it will never be perfect, that even if he finds something he thinks will be perfect, it’s going to turn out much differently than he thinks.” He grins, cheekily adding, “Also, I think he doesn’t really like to work. He might do two or sometimes three movies a year, and he doesn’t want to dedicate all that time to just one thing.”

Given that he’s known Damon most of his life — Affleck was just five years old when Damon and his big brother Ben became best friends in their hometown of Cambridge, Massachusetts — he feels confident enough in their relationship to give him a gentle ribbing. They’ve also appeared in numerous films together, starting with the 1997 drama Good Will Hunting, which won Damon and Affleck the elder an Oscar for Best Original Screenplay, all the way to Oppenheimer, this year’s Academy Award-winning Best Picture.

Given that they’ve known one another for so very long, Affleck is able to gently poke at his friend, though —kidding aside — he truly did want Damon to direct his labor of love. “He’s very smart about stories and performances. He’d be a good director. When I sent him [the script] he said, ‘No, I’m not going to direct this.’ But then, his wife, Lucie, read it. She’s a lot smarter than he is. She said, ‘This is good. You should do this, at least as an actor.’ And then he said, ‘OK, I’ll do this as an actor.’ I then asked him to ask Doug Liman, who I’ve always wanted to work with, to direct… and he said yes [with the caveat] that the third act be rewritten. Having spent a lot of time on it already, I realized I was actually just at the beginning of the process, because Doug came in with a million notes and suggestions. So did the producers, and so did Matt. And it became a group effort.”

Together, the boys headed back to their native Boston to begin filming last March, in locations that included Fenway Park, Wollaston Beach, the North End’s Bova’s Bakery, and Boston City Hall [though interiors were shot in New York because Liman and Damon, who live in the city, preferred to be closer to their families]. They also enlisted a slew of new additions, including industry vets Michael Stuhlbarg, Paul Walter Hauser, Ving Rhames, Alfred Molina, Toby Jones, and Ron Perlman, as well as a newbie, musician Jack Harlow.

If anyone is thinking, ‘How the heck did this motley pairing come to be?’ the answer is pretty simple. Affleck was actually giving his best Kerouac, driving the all-electric Polestar 2 from the southern border of the country to the north for Haute Living in 2022, and decided to pitstop at the Outside Lands music festival in San Francisco, where Harlow happened to be playing. “I didn’t know him at all, but we had a friend in common, who connected us. I didn’t know much about him, but I liked him right away. He was really smart, funny, sharp, and quick-witted. He had just shot a movie, White Men Can’t Jump, which was in post-production, and had a lot of questions about the process. It was clear that he liked movies and wanted to act, so when The Instigators came around, I thought Jack would be perfect for it. Everyone was a bit surprised, because he’s only done one movie and is known for his music, but after a 20-minute call with Doug, he was cast right away. Doug is very smart about casting; he’s very intuitive. And Jack knocked it out of the park — every scene that he’s in. He’s one of those people who is so creative that it crosses over into everything he does.”

As is Affleck himself, I remind him. Self-doubt aside, his film is truly funny — as is he in it. Plus, now that he’s tried his hand at comedy, he has the bug: this particular genre is definitely something you’ll see him exploring again in the future.

“I hope to do more of it,” he discloses, before confiding, “The reason that I had to write this one and try to put it together myself in the first place is because no one was sending me their best comedy scripts. Maybe that will change now, but sometimes, change is slow. Everyone says it just takes one — it just takes one hit to be a movie star, it takes one moment to change everyone’s mind — but I don’t find that to be true. It seems like you have to do something very slowly, and only then will people start to change their opinion. I do hope I get to do another comedy one day, but so far, nothing’s come my way.”

At least he’s taking matters into his own hands, which shows a true amount of ingenuity. And what’s more, he doesn’t plan on stopping with comedy alone. Life, he says, is about taking risks, testing yourself, and seeing what you’re made of.

Which is why he even considered two specific upcoming projects, which include a music video for Zach Bryan — whom he became a die-hard fan of after meeting the country singer in LA recently — as well as a potential Biblical project that he’s considering filming in Morocco this fall. Both the “Oak Island” video and the story of Joseph and Mary’s attempt to protect baby Jesus — what Affleck refers to as a “sweeping Biblical epic” revolving around ruler of Judea King Herod’s decision to kill all of the kingdom’s babies to secure his own position on the throne after a prophecy reveals that a new king will be born — are true departures from anything he’s done previously, the latter in particular.

“It’s different than anything I’ve done before, and I felt like it was hard to imagine myself doing it. But sometimes, that’s a good reason to do something in the first place. It’s something I should have been doing all along,” he says, scratching a beard peppered with gray that he’s meant to be growing for the potential film, but which, quite frankly, he can’t stand — especially in the current LA heat.

“I want to have amazing, fun adventures, living [my] life to the fullest. And this is what I do for a living — it’s what I love to do. But now, I feel like I should be taking more risks [when it comes to my career]. I’m less afraid of falling on my face than I might have been in the past. I’m more interested in what it’ll feel like to jump.”

He isn’t 100 percent sure what brought this adventurous, devil-may-care mentality on, but if he had to guess, there are a few of the usual suspects.

“Maybe it’s about getting older. Maybe it’s just because I’ve been sitting around for the last four years. I’ve seen so many unexpected, challenging curveballs. The industry has changed a lot, the culture has changed a lot — the pandemic, so many strikes, so many things going on that kind of made me think that now is a good time to do stuff that I haven’t done.”

But what he has done thus far is impressive. Affleck got his start in 1995 at the age of 18 in the black comedy To Die For alongside Nicole Kidman and Joaquin Phoenix, and in 2007, was nominated for his first Academy Award, a Golden Globe, and a Screen Actors Guild Award for his breakthrough performance in the drama, The Assassination of Jesse James by the Coward Robert Ford. He received universal acclaim for his work in Kenneth Lonergan’s Manchester by the Sea, winning an Academy Award, a BAFTA, Golden Globe, Critics Choice, Gotham, and Independent Spirit Awards for Best Actor. He was also honored with over 40 regional critics prizes, including the New York Film Critics Circle and the National Board of Review. He’s collaborated with director David Lowery on three auspicious films, including 2013’s Sundance prize winner Ain’t Them Bodies Saints opposite Rooney Mara; made his directorial feature debut in 2019 with Light of My Life, which he wrote, produced, and starred in, as well as popular films such as Gone Baby Gone; Interstellar; Our Friend; Out of the Furnace; Steven Soderbergh’s Ocean’s trilogy; and 2023’s Christopher Nolan-directed Oppenheimer, among others. He’s appeared onstage, making his West End debut in 2002 in Kenneth Lonergan’s award-winning play This Is Our Youth, and founded Sea Change Media, where he develops new works from emerging filmmakers of diverse backgrounds, telling stories that aim to entertain audiences and inspire conversations.

His career has been robust, full of critical acclaim, awards, and praise, but now he’s ready for a change, to do something new that fulfills him creatively. Beyond comedy, he says that he’s looking to other genres within the acting realm, though travel writing, and travel in general, seems to excite him. But expanding into unknown areas within an industry he’s mastered seems like a great place to start taking the right kind of risks — calculated ones.

“It’s a little bit harder to jump into those other things I’ve always wanted to do,” he admits. “Taking risks as an actor means choosing different projects, working with different people, challenging myself. [That said], all of the infrastructure is in place. It’s like, I’m in a car, and I’m just going to take this street instead of that street. Outside of acting, I don’t have that infrastructure yet. I don’t know exactly how to do it. I am interested in a lot of other things, but there’s a steeper learning curve. I write and act and direct and produce movies. I write to unclutter my head and make a document of the things I’m imagining before the next thing barges in. I direct because it’s fun to then bring all that writing to life, as they say. So, I have to figure that out, and I really want to.”

He tried, once upon a time. After the success of his first film, he opted to go back to school, enrolling full-time at New York City’s Columbia University, where he majored in physics. Later, because of his mother, who had been a mediator, he became intrigued by the juvenile justice system, and started to facilitate restorative justice practices for teens who have been diverted from the real judicial system by working with New Earth, an LA-based organization that offers alternatives for incarceration to young people. Although he considered working with them full-time and found satisfaction doing the work, ultimately, he realized it wasn’t his path (though he still serves on its board).

“[For a long time] I’ve gone around and met people that do different things, spending a lot more time interrogating what they do, and why and how they do it, so that I can educate myself. My interest in how people behave and why — and what it says about all of us curious and lost people — is satisfied sometimes by doing other things, like the conflict resolution in juvenile justice that I have done. Human drama is interesting; it tells me a lot about the drama in my own head and the drama swirling around me.”

There’s more good that he’d like to do, too. “I’d like to completely rebuild the foster care program in this country. Even Massachusetts, my home state, a fairly wealthy and historically progressive place, could do so much better. I’d like to start a program that plans incredibly challenging life episodes. You are washed up on an island with nothing.  You stay there for a year. Alone; your own Cast Away experience. It’s expensive because we monitor the experience without giving you the comfort of a “come save me” button. I want to go back to school. I want to learn about everything. I want to plan a city from scratch. I don’t want to work for a living — I want to work for God. You know what I’m saying? But I don’t always. I often work for a living so I can pay for others’ lives. And I love doing that.”

Regardless of what route he goes now, Affleck isn’t planning on making any changes until the youngest of his two sons — 16-year-old Atticus (he also shares 20-year-old Indiana with ex-wife Summer Phoenix) — heads to college. Until then, he’ll take his moments as they come, trying to live his best life.

“I’m very happy with where I am at,” he admits. “I love my kids so much, and it’s a joy to see them grow up at these ages. I like the way I am less bothered by bullshit; it almost doesn’t appear on my radar anymore. I can’t smell it. Life is good right now. I’m grateful even for all the inexplicable and undeserved hardships I’ve had to deal with in life — even those seem to have strengthened me.”

Which is why, one major upcoming milestone doesn’t seem to phase him at all. His 49^th birthday falls on August 12, and one year from now, he’ll turn 50. But really, what can 50 do to him? It’s just a number, after all.

“Fifty is coming, and I know that [on paper], 50 is a big one. [That said] the last ten years have been the hardest of my life. I’m sure there are a lot of trials ahead — predictable and big surprises — but I have new tools in my box for dealing with [them] because of the last decade of my life for sure. [And so] 50 isn’t actually significant. It seems so because we use the base-ten system of counting, but I don’t feel a biological or otherwise organic significance.”

In reality, there’s nothing this number can do to hurt him; he’s already gone through hell, and he kept going. He deserves to have some fun. Which is maybe why he’ll choose to celebrate in a destination known for being a good time — such as, surprisingly, a place he loves: Las Vegas.

“I’m not dead yet! I still like to have fun,” he insists.

I didn’t see that one coming, but he says he’s very into what Sin City has to offer for a few reasons — another onion-like revelation from an actor who seems so serious and stoic onscreen. Although he’s all about the newly opened Fontainebleau, dining at Evan Funke’s Italian hot spot Mother Wolf, with the occasional nightclub outing thrown in for measure, the real allure of Sin City, he says, is in placing bets and playing cards at the Fontainebleau Sportsbook. He’s a gambler, you see, a risk-taker.

Affleck tries to explain what it is that appeals to him, bringing it back to not just his career, but his life. “I like imagining there really is a flow, a tide in the cards, and trying to find it. ‘There is a tide in the affairs of men,’ said The Bard. I don’t think he meant cards, but even so… I did movies I was interested in, with people I was interested in working with, instead of trying to make ‘strategic career choices.’ That has been good and bad for me. I doubled down on what attracted me, knowing the outcomes were unlikely to be ‘successful’ in the bigger picture. Long odds bets on teams I wanted to root for.”

And regardless of what the outcome has been or will be, it’s important to know that Affleck has always bet on himself — and that is and always will be a risk worth taking.