Lizzy Caplan has built a career out of playing salty sidekicks: the goth foil Janis in Mean Girls, the cater-waiter-coworker-with-benefits in Party Down, a love interest in Hot Tub Time Machine, and a hallucinated sister in 127 Hours. In her new show Fleishman Is in Trouble, Caplan’s character too, starts out on the sidelines. Adapted by Taffy Brodesser-Akner from her 2019 novel of the same name, the FX on Hulu limited series initially centers on nebbishy Manhattan surgeon Toby Fleishman (Jesse Eisenberg) and his imploding marriage to mega-agent Rachel Fleishman (Claire Danes). Caplan plays Toby’s old college friend Libby Epstein, a former magazine journalist now floundering in suburban stay-at-home-mom exile. Ever so gradually, it becomes clear that though someone else’s name is in the title, Libby is closer to the center of the story than she or the viewer first realizes. She’s also the series’ narrator, overseeing the action throughout like the Voice of God.
“In early conversations, Taffy wanted to reassure me that there was a payoff for Libby,” Caplan recalls, chatting with Vanity Fair by video from her Los Angeles home, where her infant son’s howls occasionally can be heard from the other room. She needed no reassurance about the role. Having so much experience with spicing up secondary characters, Caplan knew how to wring substance out of a brainy, marginalized figure like Libby.
“In many ways, I identified with Libby more than I’ve identified with any other character I’ve played,” Caplan says. “It’s like the East Coast version of my West Coast Jewish upbringing.” She laughs when I point out that she’s one of the rare celebrities whose Wikipedia page makes note of their Bat Mitzvah and Jewish summer camp pedigree—her ancestors would be kvelling! Fleishman’s mostly Jewish cast startled her. “I’ve never once been on a set with all Jewish actors—not once!”
Another element that connected with Caplan is her character’s growing understanding of how misogyny shaped her career. Magazine journalist Libby believed herself to be one of the guys and expected to be judged on merit—but the “guys” always saw her as an outsider. “The one of the guys thing…I was that girl, which now is such an eye roll to me,” Caplan says, without rolling her eyes.
Caplan’s career fate was sealed at the age of 15, after she took an acting class at her Los Angeles performing arts-focused high school and caught the bug. She found a manager’s assistant who sent her on a flurry of auditions. “In my mind, I was going to land the leading role in everything immediately…a lot of Shakespeare, and heavy-hitting Oscar fare,” she says self-mockingly. “Then I booked my first job, which was Girl #1 in the pilot of Freaks and Geeks. I had one line, and I remember being like, Should I do this? Luckily, they convinced me that yes, I should do this. And, miraculously, that became a recurring thing.”
Fox famously canceled Freaks and Geeks after a single season, and Caplan discovered that Hollywood of the early 2000s was not craving idiosyncratic, barbed-tongue young women for lead roles. She is grateful for that now. “When you start acting so young, you’re figuring out who you are too. And it’s why it’s so dangerous if you actually do become really famous,” she says, hugging her knees to her chest. “You’re fixed as this thing that you were chasing when you were f*cking 16. No teenagers should ever be actors!” But Caplan says she lucked out, because Freaks and Geeks set her on the right path. “Before I had any agency at all, before I could make any decisions on my own, I was kind of put on this trajectory that I am on. I don’t know how it happened. It’s like some cosmic thing that I’m honestly forever grateful for because it could have gone any number of different directions.”
Her first big movie, Mean Girls, made her an icon to snarky goth girls like me, who rarely saw versions of themselves in pop culture back then. Wary of being pigeonholed as a broody misfit, Caplan briefly tried her hand at being an ingenue on the youth-saturated WB network, dying her hair blond and sporting a spray tan for the series Related. “I remember wanting to be in Smallville more than anything,” she says with a husky chuckle of another WB show she appeared in. “I could have ended up living in Vancouver for 10 years and potentially would have been the number two of the NXIVM cult!”
Caplan thought she’d landed her big break in 2006, when she was cast in The Class, an ensemble comedy from Friends cocreator David Crane that was expected to be a monster hit—to the point that director James Burrows flew the whole cast on a private jet to Las Vegas and gave them the same speech about stardom that he’d delivered to the Friends actors before that show premiered. “It was heartbreaking at the time,” she admits but says she’s never really yearned for mega-fame.
I ask her if her six-year relationship with Matthew Perry post-Friends contributed to that distaste for stardom. “I was never interested in that life,” she says, sipping on the dregs of an iced drink. Perry doesn’t mention her by name in his new memoir, but he does throw in an odd, oblique anecdote about a “woman I’d dated for six years” who went on to date a British guy. (Caplan married British actor Tom Riley in 2017.) Not only did this ex decline an invitation to attend his debut play in London, he writes, but “a while later I got back an email telling me that she was getting married and that she had no room in her life for friends.” Caplan says she hasn’t seen the book and smiles placidly when I relay the anecdote. “I don’t remember that! I really don’t know much about the book or anything.” She shrugs. “You know, I have no ill will. I hope the book is really successful.”
