Stepping into his first major dramatic acting role after an acclaimed career in comedy, Conan O’Brien was understandably “very nervous,” he said, before shooting began for the A24 film “If I Had Legs I’d Kick You.”
In fact, the Brookline native admitted during a recent interview with the Globe over Zoom that he even tried talking writer-director Mary Bronstein out of casting him in the film altogether after they first met (“He didn’t win that battle,” joked the filmmaker), ultimately saying yes, thanks to her confidence in him.
“I just didn’t want, in any way, to jeopardize this thing she had made,” said O’Brien, 62. “But Mary said, ‘You can do this,’ and I said, ‘OK, let’s go.’”
“I jumped into something that scared me, and I think it’s good to be scared,” he added.
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In the new film, which opens in theaters this month, Rose Byrne plays Linda, a mother whose life is falling apart as she struggles with work, living out of a motel after her apartment is damaged, and taking care of her sick daughter, whose mysterious health condition requires constant attention. She finds little sympathy from the men in her orbit, like her absent husband (Christian Slater), a cruise captain away for work, and her stone-faced therapist, played by O’Brien, who doesn’t seem all that interested in her as a patient.
“When you’re going through a period of great stress, it’s very hard to find someone to actually listen to you,” said Bronstein. “Everyone is trapped in their own reality, and sometimes that reality is hell.”
Byrne, 46, called the film “punk rock” for its “totally different take on motherhood,” praising its “ambitious storytelling.” She noted that “If I Had Legs I’d Kick You” breaks away from how past movies about women falling apart depicted them, pointing out that earlier films were too often “one note,” and fell into the trap of portraying their protagonists succumbing to hysteria.
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“Our determination [was] to bring nuance to that,” Byrne said.
“There’s so much guilt and shame that comes with being a mother and not living up to the ideal,” said Bronstein, who was partly inspired to write the movie after her experience caring for her own daughter, who faced a health challenge several years ago. “I think it was important to me to dismantle that idea.”
O’Brien described the movie as “a shape shifter,” with its more dramatic elements making it hard to peg to any one genre.
“I think this is one of those movies that you can look at it from different angles,” said O’Brien. “Is this a dark drama? Is it a really dark comedy? Is it a horror film? It’s kind of all of those things, which is amazing, but then it’s not any of those.”
The former late-night host credited Adam Sandler for getting him involved in the project. It was the New Hampshire native who “speed dialed” him, according to O’Brien, to see if he’d be interested on behalf of one of the Safdie brothers (Josh Safdie is a producer on the movie and previously worked with Sandler on “Uncut Gems”).
“I’m right between [David] Spade and Chris Rock [in Sandler’s phone],” O’Brien joked.
Praising Bronstein for having a “real vision” for the project, O’Brien called her screenplay “a really special piece of work.” Prior to filming, O’Brien hunkered down with her for a week of intensive rehearsals in Los Angeles. The director called the experience a “boot camp situation,” while O’Brien compared it to a “Rocky” montage.
By the end of filming, Bronstein saw him coming around to her approach, praising O’Brien for ultimately delivering “a proper, dramatic performance” that she believes will surprise audiences.
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“I basically taught him about why it’s important to know about the background of a character, how that informs the performance, even if it’s never said,” explained Bronstein. “And he was so not a believer in it. He was so like, ‘Yeah, I don’t really need to know where this guy’s house is, do I?’”
“But then by the end of it, he did understand, because if you see the performance, you see that it’s all in there,” she added. “I think that I made a believer out of him, and I knew he could do it.”
O’Brien said that he had “never done that kind of training before” and took the work seriously, with the Harvard alum learning his part “backwards and forwards before we ever got to the set.”
“I know how to perform in front of people and sell comedy, but this was an entirely different thing,” said O’Brien. “I worked really hard with Mary, and I thought a lot about who this person is.”
“If I’m going to do the Oscars or host the Emmys, I always would say, ‘OK, put yourself on that stage, just as you’re walking out, and [remember] how scary that is. Now, what do you have to do to be ready for that moment? Work your ass off,’” he added. “So I just applied the same rule. And it turns out that works pretty well, I think.”
For his role, O’Brien tapped into his heritage to inform the character’s discomfort with Linda’s displays of emotion during their therapy sessions.
“I’m very Irish, very Boston Irish, and we’re famously uncomfortable with strong emotion, I think, unless it’s anger,” said O’Brien. “Someone emoting like that, who’s despairing and making a mess and emotionally reaching out, the Irish tend to, you know, shrink from that.”
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“The more upset she gets, the more my character retreats and tries to keep everything in a neat little box and just get to the end of the session and cut it off,” he added.
O’Brien’s Bay State roots run deep, with the Brookline native discovering his love of movies at spots like the Coolidge Corner Theatre and the old theater at Hearthstone Plaza on Route 9, where his brother Luke used to work.
“He would see movies like 900 times because he was an usher,” said O’Brien, whose late father, Dr. Thomas F. O’Brien, played an important role as well in inspiring the young O’Brien’s appreciation for comedy. “[My dad] took me to see Chaplin. He took me to see Marx Brothers, the old classics. ... He loved ‘The Pink Panther’ movies, and made sure that I saw all of those.”
“So all of that stuff was being fed into my growing brain,” he added. The beloved kids program “Zoom” was another favorite, with O’Brien calling it “our claim to fame in Boston.”
“I used to watch ‘Zoom,’ and they would have sketches,” said O’Brien. “I thought, ‘Wow, they’re making this in Boston, and these kids are my age, and they’re making comedy.’ So all of that was so exciting to me, and it’s affecting me still.”
As for what inspires O’Brien these days, the comedian has been busy in his post-late-night years, helming a hit podcast, “Conan O’Brien Needs a Friend,” as well as his Emmy-winning HBO Max travel docuseries, “Conan O’Brien Must Go.” He’s also set to host the Oscars for the second straight year in 2026, and picked up a Mark Twain Prize earlier this year for his work in comedy (he’s pretty good at guitar, too, and performed at last year’s Newport Folk Festival). O’Brien said he’s just focused on trying things that take him out of his comfort zone.
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“I used to care so much about everything being a success, and now I’m interested in pushing myself and seeing what I can do,” O’Brien said. “If you’re working with really great people, your chances are better. So that’s something that I’m always going to be on the lookout for.”
“If I Had Legs I’d Kick You” screens at the Brattle Theatre in Cambridge at 7 p.m. on Oct. 10 as part of IFFBoston’s Fall Focus, before opening in Boston Oct. 17.
Matt Juul can be reached at matthew.juul@globe.com.