Casey Affleck steals the show from Matt Damon in ‘The Instigators’

Growing up, Matt Damon and childhood pal Casey Affleck were obsessed with one particular movie: Martin Brest’s 1988 action-comedy “Midnight Run.”

Starring Robert De Niro as a streetwise bounty hunter forced to drive cross-country with a mob accountant (Charles Grodin) adept at getting under his skin, Brest’s film was a “North star” for Damon and Affleck while the duo made their latest film, “The Instigators.”

The heist comedy, which will enjoy a limited theatrical run starting August 2 before debuting on Apple TV+ August 9, has shades of Brest’s film, even while Damon acknowledged in an interview with Boston.com that he and Affleck could never hope to replicate that “Swiss watch” of a movie.

“That movie is a touchstone for Casey and me, and has been since it came out,” Damon said. “We saw it multiple times in the theater. We saw it, I don’t know how many hundreds of times since. We talk about it all the time, we quote it all the time.”

Assembling the crew

Filmed and set in Boston, “The Instigators” stars Damon as Rory, a depressed ex-Marine who needs money fast. Desperate, the previously clean Rory teams up with bumbling small-time criminal Scalvo (rapper Jack Harlow) and recently released ex-con Cobby (Affleck) for a robbery.

“If you couldn’t get the A team and the B team and the C team weren’t available, you get ‘The Instigators,’” Damon said.

The heist, masterminded by the enigmatic Mr. Besegai (Michael Stuhlbarg), is distinctly Boston in nature: The city’s exceedingly corrupt mayor (Ron Perlman) is holding a black-tie fundraiser on the eve of a hotly contested election, and the all-cash, untraceable donations are ripe for the taking.

Perlman’s Mayor Miccelli has shades of former Boston mayor and Massachusetts Governor J.M. Curley, who served prison time during his final term in office. But for a more recent inspiration, “The Instigators” screenwriter Chuck MacLean (“City on a Hill”) turned to Rhode Island.

“Chuck went to Brown, and when he was there, Buddy Cianci was the mayor, and very famously got reelected from prison,” Damon said. “So it was kind of a nod to that old-world kind of East Coast politics.”

When the robbery attempt inevitably goes wrong, Rory and Cobby go on the run. As two townies who’ve never even been to Canada, however, they don’t make it far. During one detour, they visit Rory’s therapist (Hong Chau), who tries to negotiate their surrender. When it becomes clear that the trigger-happy cops won’t take the two alive, Chau’s Dr. Rivera agrees to pretend to be the pair’s hostage as they make their escape.

Chau, a BU alum who worked with Damon on Alexander Payne’s 2017 film “Downsizing,” said she probably wouldn’t have joined “The Instigators” if it wasn’t for him — a comment that earned a joking protest from Affleck during the trio’s interview with Boston.com at the Mandarin Oriental Hotel in Boston.

“Before even reading the script, just the idea in my mind of something like a muscular action movie sounded really intimidating to me,” Chau said. “But once I heard that Matt was doing it, I was like, of course.”

As a producer of the film along with Ben Affleck through their company Artists Equity, Damon teamed up with director Doug Liman to make sure the cast of “The Instigators” was stacked with talent.

Alfred Molina (“Spider-Man 2”) plays Mr. Besegei’s right-hand man, Ving Rhames (“Mission: Impossible”) plays a renegade cop, and Paul Walter Hauser (“I, Tonya”) plays a hitman brought in to clean things up.

“Doug was smart enough to cast people who were actually really, really good at being funny,” Affleck said. “Alfred Molina could be really funny with just a look.”

Casey Affleck in the spotlight

Though Damon is first-billed on the film, “The Instigators” is really a showcase for Affleck, who co-wrote the screenplay with MacLean.

Cobby may be a mess — in an early scene we see him use a small child to bypass the breathalyzer on his motorcycle — but he’s the more competent and streetwise of the duo. He also gets all of the film’s funniest lines, with Damon playing the frustrated straight man.

A self-described “class clown” in high school at Cambridge Rindge and Latin, Affleck told Boston.com that “The Instigators” fulfilled a long-held desire to make a comedy of his own.

“I’ve wanted to do comedies for a long time. In fact, I thought that some of the other movies I had done were comedies,” Affleck said jokingly. “But at some point I understood that I had to make a bigger effort to try to be involved in one.”

For a long time, Affleck’s most notable comedic moments came playing a bit part as a bickering sibling, whether begging for his double burger from Ben Affleck in “Good Will Hunting” or winding up Scott Caan in “Ocean’s 11.”

That changed in 2016, when Affleck played a “real” Dunkin’ Donuts customer in a sketch on “Saturday Night Live.”

Eight years later, the two-minute clip has made Affleck the unofficial avatar of a certain type of Bostonian, something that came as a surprise to Affleck.

“I kept saying, like, why are we doing this? No one is gonna get it,” Affleck said. “No one outside of the three blocks where we’re shooting this thing, anyway. But then it seemed to work.”

A quintessential Boston movie

“The Instigators” is hardly the first Boston crime movie. But it may feature the most effective use of the city’s biggest landmarks ever captured on the big screen.

Damon, Affleck, and Harlow begin their heist planning in the bowels of Fenway Park. When Rhames wants to send a message to the fugitives, he visits Bova’s in the North End and smashes every single glass display case. Late in the film, an explosive hostage situation engulfs City Hall.

Most notably, Damon, Affleck, and Chau lead Boston police on an extended car chase that begins in the Back Bay and winds up on the Esplanade.

According to producer Kevin Walsh, the city had never shut down the Esplanade for filming before. Damon, no stranger to car chase scenes thanks to his work with Liman in the “Bourne” franchise, was left in awe.

“Everybody’s walked out there. Maybe sometimes you see a state trooper out there, but that’s it,” Damon said. “A civilian car chase going down the Esplanade? I was like, wow, this is big. This is really cool.”

“The Instigators” will be released in limited theaters on August 2 before streaming on Apple TV+ starting August 9.