Why Conan O’Brien Is Deliberately Cast Against Type in If I Had Legs I’d Kick You

Long before she became a filmmaker, Mary Bronstein developed an interest in therapy and what they call “the talking cure.” Psychology is what she got her master’s in prior to attending NYU’s Tisch School of the Arts; and in her second feature as a writer-director, the cryptically titled If I Had Legs I’d Kick You, Bronstein sets the story of her “emotional avatar” in a therapist’s office. There Linda (Rose Byrne) works as an absolutely burned-out psychoanalyst—and a woman who is also utterly convinced her own therapist down the hall (Conan O’Brien) despises her.

“I’m a big proponent of therapy, I believe in therapy, I’m in therapy,” Bronstein smiles when we catch up with her ahead of If I Had Legs’ premiere at Fantastic Fest. “But I’ve been in and out of therapy since I was a young teenager. I’ve had good therapists, I’ve had bad therapists, I’ve had every kind of therapist. And there’s a part of therapy that doesn’t help somebody like Linda, which is the part where there’s boundaries, and there’s a lack of human connection. It’s a one-sided relationship.”

The Linda that Bronstein refers to is Rose Byrne’s central protagonist (and some might say her own self-actualizing antagonist) at the heart of If I Had Legs. In a performance that’s been generating Oscar buzz for nearly a year since its earliest screenings at Sundance, Byrne is extraordinarily bitter, funny, and exasperated as a woman at the end of her rope—including opposite another remarkably unexpected performance via the actor playing her curmudgeonly psychiatrist, Conan O’Brien. He is a man who respects the boundaries of the therapeutic process: you don’t hang out with your patients; you don’t command your patients; you don’t even necessarily like your patients. But in the case of the dynamic between himself and Linda, boundaries also become walls ready to crash on both their heads.

“There’s boundaries, and there’s reasons for that, it’s appropriate,” Bronstein notes. “But when you’re having someone like Linda in your office, begging you to tell her what to do, to not say a ‘therapy thing,’… that’s the limitations of therapy. That woman needs a hug. She needs a hug so bad. And she’s not going to get it from him.” 

It’s a striking dynamic in a film that hits hard from a variety of angles. When we first chat with Bronstein, it is again at Austin’s premier genre festival, a fest celebrated for its horror and suspense programming. And while we’d hesitate to quantify If I Had Legs as any single specific genre, it was nonetheless the most intense and anxiety-inducing experience we had at that festival. A fact which makes Bronstein beam with visible pride since she admits to taking from the “cinematic language of horror” in Legs. (Perhaps unsurprisingly, she counts William Friedkin’s psychologically-laden approach to The Exorcist as a formative movie-watching experience.)

In Friedkin’s film, very well-played and reasoned men of science fail to help several women dealing with an expanding crisis. One imagines Linda, and her viewers, can relate. Whether it’s Fantastic Fest, Sundance, or when we catch up with Bronstein again on the eve of her film’s New York Film Festival bow—a kind of grand finale before A24 releases the movie to wide audiences this fall—If I Had Legs has been shocking audiences as much with its tension as its humor. And the fact that Bronstein intentionally cast a famously funnyman to play a guy without an ounce of humor in his bones.

“My superpower in life, if I have one at all, is I like to connect with people, and I like to make them feel comfortable,” Conan O’Brien confides. “That is something that I do habitually, all day long…that’s something that’s in me. So one of the things that’s been so fascinating about this experience is not being able to use any of that in this character. That’s not what I’m doing, and my attempts to even think I’m trying to help, those attempts are laughable. I am someone who has a lot of tools in that particular chest, and I can’t use any of them, because I don’t have them in this part.”

It was the fear of doing something so far out of his comfort zone as a performer—in this case of a particularly dramatic variety—that enticed O’Brien in the role. Yet it was the earnestness of his humor that caused Bronstein to think of a childhood hero for the role in the first place.

“I’ve been a fan of him and his original late night show since day one,” Bronstein says of O’Brien. “I was a huge Letterman fan, so I was like, ‘Who’s this guy who’s gonna take over the show?’ And I watched the first episode and I was blown away. I couldn’t believe the stuff he was doing. He was so loose [in this] no-adults-in-the-room comedy. It was like ‘how is this on television?’ So I always had this sense of him as a guy willing to take risks and not being precious with himself.”

The idea to reach out to O’Brien came to Bronstein after listening to the former late-night host interviewing his own idol, David Letterman, on the podcast Conan O’Brien Needs a Friend. Here were two iconically funnymen having a decidedly unfunny, pensive conversation about the craft. And yet, even by the very nature of the podcast’s name—Conan O’Brien needs a friend—there is something pitifully human and melancholic to O’Brien’s humor that Bronstein knew she could use.

“The character is so buttoned-up, so repressed and so oppressed by his own patients—and that’s Conan,” says Bronstein. “It’s a part of him and a part of his humor from the get-go. When you think of some of the early comedy bits that would be on the show, it would involve stuff like someone threatening to shoot a puppy. That is dark. But it’s funny. And that’s a hard line to do, and if there’s a self-deprecation in his humor, it’s not false; it’s very intelligently [used]; it’s someone who understands human emotions.” She ultimately surmises, “Conan’s voice is so calming to me and familiar to me in that way. And if he told me to do something, I would listen.”

O’Brien deflects any such compliments with a smirk, but he is quick to return them. According to the newly dramatic thespian, he spent hours every day rehearsing with Bronstein. “Mary is incredibly tenacious,” O’Brien notes, “and you feel that, and all my people-pleasing went into ‘I want to make sure I please this insanely driven person with a vision.’”

That vision is again in service of a unique perspective on a woman’s struggle in crisis. While the inability of O’Brien’s therapist to help, or even connect, with Byrne’s Linda is a core facet of I Had Legs I’d Kick You, it is just one of the many simultaneous crises occurring at once in the film. Additionally, Linda is grappling with the fact that her husband (Christian Slater as a mostly disembodied voice over a telephone) is out of town on work while his and Linda’s daughter is left to struggle with an undisclosed illness. We are told in the film by the child’s physician (Bronstein herself in a cameo role) that it is not necessarily life-threatening, but there is still an overwhelming sense of oppression around Linda, a sensation heightened since we never see the daughter’s face; we only hear her pleas for attention or help while observing a beleaguered Byrne.

“That was one of the first conceptual things I came up with,” Bronstein says, “and it’s in the first draft of the script. It’s a big swing to take, because I haven’t seen it done in a movie, but my idea is… she can’t see her daughter as anything in this moment but as an obligation, an obstacle, something that’s made her life really hard. She can’t see her for who she is, which is a little girl who needs her mom.”

It is ambiguous whether the daughter’s cries and screams are as constant as they feel in the movie, but in Linda’s world there is only one truth. Well that, plus the ones inflicted by judging eyes from people like her child’s pediatrician, Dr. Spring (Bronstein).

“Linda’s a woman who outside the story, say a couple years beforehand or maybe a couple years into the future, she’s always a little bit of a chaos agent, always a little bit of a disaster,” Bronstein considers. “But she’s the woman you always want at your party, she’s going to be the most fun, but when she’s upset, she’s going to be the most upset. She lives in extremes.”

Once again Bronstein notes the film is not autobiographical, but she sees herself in Linda. “There’s a lot of me in it,” Bronstein confides. During our first interview she even points to a piece of chewed gum that, like Linda, she’s placed on the side of her mug of green tea. “That’s Linda, that’s me.” It might be the reason she cast herself as one of Linda’s chief antagonists: “It’s me talking to myself, really. She’s the part of me that’s like ‘get the fuck out of bed and do the laundry.’”

Yet there is something universal about her experience. O’Brien, for one, notes that in the growing distance between Linda and her off-screen husband, he saw his own experience during his famed Legally Prohibited from Being Funny on Television Tour.

Says O’Brien, “I was on tour when my kids were really little, and my wife called me up in extremis about something, and I’m on a tour bus, and people in the background are like ‘yee-haw!’ And she’s just like, ‘I’m glad you’re having fun!’ And I’m thinking I’m doing a 30-city tour, I’m working my ass off, but yeah.”

Depending on someone’s perspective, an event can be trivial or existential, funny or abject dread-inducing. According to everyone who made the movie, If I Had Legs is all of those things at once.

“Sometimes, someone will show you an optical illusion, and they say stare at this, and immediately you see a rectangle,” O’Brien observes. “But if you keep staring, you see a triangle but then you see a rectangle. I feel that way about this film, which I think really speaks to what Mary’s pulled off. I can see it as horror. I can also see it as straight drama, I can see it as comedy, and then I switch back again. It’s why all my friends who have seen it so far have said afterward, ‘I really need to talk to you about this.’ And they get me to change my mind, but then their mind changes and my mind changes. It’s a shapeshifter.”

If I Had Legs I’d Kick You will take shape in limited release on Friday, Oct. 10 and nationwide on Oct. 24.