Lizzy Caplan on the Lucky, Miserable People of 'Fleishman Is in Trouble'

actor lizzy caplan shown in a dramatic portrait with her hair up, eyebrow arched, in a black and floral bodysuit tucked into jeans
Lizzy Caplan on Marriage, Misery, and 'Fleishman'Cibelle Levi

Spoiler alert: Fleishman Is in Trouble is about two flawed humans with different perspectives on the same life events. The fact that this feels like the kind of plot twist that requires a warning is a testament to the narrative trickery of both the best-selling 2019 novel by Taffy Brodesser-Akner and the eight-episode miniseries debuting today on FX.

Fleishman, we’re led to assume at the start, is Toby Fleishman, a recently divorced Upper East Side hepatologist in his early 40s played by Jesse Eisenberg. But there’s another Fleishman in this story, his ex-wife, Rachel, a tough-as-nails talent agent played by Claire Danes. (Danes is sort of a Chekhov’s gun in a show like this. You know there’s going to be a cathartic crumple-faced cry at some point. You just don’t know when.) Is this a story about Toby, or about Rachel? The answer, of course, is yes, but as our narrator, Libby, played by Lizzy Caplan, points out, people are more likely to care if they think you’re talking about a man.

It’s important to know that Adam Brody is in this show along with Eisenberg, Danes, and Caplan, which means that for some viewers, it’s going to feel like watching Mark Zuckerberg divorcing Angela Chase and complaining about it to his friends Seth Cohen and Janis Ian from Mean Girls. The cast is a murderer’s row of Old Millennial actors, all confronting the existential challenges of middle age and long-term monogamy. Caplan, reached via Zoom on a chilly day in Los Angeles, thinks this adds a layer of meaning to the project. “Hopefully, it makes the audience feel like they’ve known us since we were teenagers. You can almost see these characters hanging out, because you feel like you have a shared history with them. You’ve known them forever.”

Certainly that’s true of her career: She started out on the critically acclaimed Freaks and Geeks in 1999, had roles in—among other things—Mean Girls, Cloverfield, True Blood, and the cult comedy Party Down, and spent three years playing the sex researcher Virginia E. Johnson on Showtime’s Masters of Sex. As the narrator in Fleishman, she’s less sidelined than one might initially think. Libby is a stay-at-home mom in suburban New Jersey and, like the novel’s author, a former men’s magazine writer. She’s narrating the story, but she’s also impacting the plot, and as the series progresses, it becomes more and more about her own angst about her receding youth and her mostly solid marriage (to Josh Radnor, Ted from How I Met Your Mother—another millennials-coming-of-age sacred text.)

Fleishman is set in the summer of 2016, a time at once so recent and so distant from our current era that it often feels oddly like a period piece. The questions it raises about marriage and happiness, though, seem almost more relevant now, given the strain of the last few years. I’m the same age as the Fleishmans, and in the month between accepting this assignment and writing the story, I learned of not one, not two, but four different couple-friends splitting up.

The show would like to point out that breaking up is hard, but so is staying together. “[Libby] doesn’t want to get divorced, but she’s so unhappy and feels so trapped. And so, she is trying to navigate a different set of circumstances from Toby and [Rachel],” Caplan says. “It’s less about I don’t wanna be with my husband and more about How do I get back to who I was, because I do not feel like myself anymore and I haven’t in so many years? And I think that’s a story that is pretty universal and not as talked about and so painful.”

lizzy caplan holds a mug of coffee and stands on a deck in the fx miniseries 'fleishman is in trouble'
Caplan stars as Libby in Fleishman Is in Trouble.Photo by Matthias Clamer

Toby, Rachel, and Libby have made it past the challenges of youth. Their lives look great on paper. They don’t have to worry about money (although they do—much of the show revolves around Rachel’s obsession with securing their plush Upper East Side lifestyle, even though it makes Toby utterly miserable). “There’s a line, I think it’s in the last episode, and it’s like, ‘How can you be so unhappy when you’re so essentially happy?’” Caplan says. “I haven’t seen a story like this in a while. I feel like we used to talk about existential things and feelings in films and TV more than we do now.”

Partly, she says, that’s the result of the ways Hollywood has changed. But it also has to do with the state of the world: “Sitting around thinking about your own problems, for so many people, feels so trivial, but the feelings are still there, and there’s importance to the feelings that you have about your own life. There just doesn’t seem to be a lot of space to talk about them right now without looking like a dickhead, I guess.”

Libby is a clear author stand-in, and Brodesser-Akner—who also helped adapt and executive-produce the show—is a very specific kind of author: the rare magazine writer with an obsessive following and an instantly recognizable voice. Caplan approaches the role with her trademark sardonic watchfulness. Her saucer eyes seem to be filtering the whole world, and her narration is laced with humor. “Taffy and I vibed immediately,” Caplan says. “She says stuff that people, I think, are maybe a little nervous to say. Talking to other mothers about how you feel about motherhood is a fucking minefield, and she doesn’t care. And I think it’s really refreshing.”

Caplan married actor Tom Riley in 2017; they have a baby named Alfie (“a 13-month-old—an old baby”). That’s a new and tender place to be in a relationship compared with the battle-hardened character she’s playing, but she says she was still able to relate. “It felt very appropriate for where I was in my head, even though it was very different than how I was feeling about my own life,” she says.

The actress first encountered the script while pregnant during the pandemic, living “this sweatpants existence,” as she describes it, and “thinking about these massive life shifts that were occurring: the idea of settling down, having a family, starting this other chapter, which still feels utterly bizarre to me. I genuinely feel like I’m far too young to have a baby at 40 years old,” she laughs.

lizzy caplan, as libby, sits across from jesse eisenberg's toby in a coffee shop as he explains his troubles
Lizzy Caplan with Jesse Eisenberg, who plays Toby Fleishman, in the series.Photo by Matthias Clamer

Next up, she’ll be on an animated Netflix show called Inside Job Part 2, which actually debuts tomorrow, November 18. She’s also playing murderous ex-girlfriend Alex Forrest in a remake of the classic erotic thriller Fatal Attraction, wrapping filming right after our Zoom. A book editor with a Meatpacking District studio and a wardrobe of incredible leather jackets, Alex seems ripe for a feminist reimagining. “We definitely go into [Alex’s] history and why she is the way that she is,” Caplan says. “I don’t think it’s heavy-handed, but I think we deliver in that way.”

She adds, “It is so fundamentally dated, and yet it feels completely not dated,” of the ’80s film. “I find it’s impossible to view that movie through the lens that the original audiences viewed it. I already felt something for Alex that wasn’t just like,She’s got to fucking die.’”

Which, maybe, brings us back to Fleishman, and the appeal of stories that force you to consider multiple perspectives. “Right now, it feels like the culture is so quick to forget that that is a rule of being alive: Try to think of where the other person is coming from, instead of tribalism. The book and the show are very effective, how they set you up to have all these feelings about Rachel Fleishman—how easy it is to only see your perspective. It’s very rich. I hope people like it. I hope it makes everybody laugh. And I really hope it makes everybody cry.”

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