Eighteen months ago in the dead of a punishing winter night, Leslye Headland was directing the show of her bizarro dreams while dodging airborne trash. “We were shooting until six in the morning,” she recalls, wincing. “After a while, people were throwing their garbage at us. East Villagers were screaming at us, ruining our takes. They were over it!” Lightly harrowing as the experience was, Headland can’t blame them. And besides, the shoot might have been a pain, but it was for “Russian Doll,” the wildly trippy Netflix series she co-created with Natasha Lyonne and Amy Poehler that dropped in February and changed her life forever.
“I’m trying to enjoy it, but I’m in shock,” Headland says over a strong coffee at SoHo’s Ludlow House social club, of which she’s a member. Not even mid-filming assurances from her wife — “Russian Doll” actor Rebecca Henderson, with whom she lives in Bed-Stuy — could prepare her for the eventual praise. “I’ve been in shock all year. I’m shocked that we pulled it off, and I’m shocked that people liked it.” (She’s tight-lipped about the second season, but maintains she’ll “definitely still be involved” while developing other projects.)
“Liked it” is an understatement: “Russian Doll” became a critical sensation and earned 13 Emmy nominations, including outstanding comedy series. Headland herself received two nods, for writing and producing. “It was so ambitious on so many levels, and such a huge payoff,” she says. “It taught me so much in the sense of risk versus reward.”
Headland, a prolific playwright and director, has spent most of her career achieving that kind of balancing act. She moved to New York 20 years ago when she got into the rigorous Playwrights Horizons Theater School at NYU’s Tisch School of the Arts. “You were studying acting, directing, design, stage management and dramaturgy,” Headland explains. If that sounds like a lot…well, it was. A popular campus joke to describe her cohorts went like this: “how many Playwright students does it take to screw in a lightbulb? Four: one to do it, and three to crack under the pressure.”
But Headland learned how to juggle duties and woo potential collaborators; she even helped throw some “infamous” off-campus fundraiser parties to get productions off the ground. As she puts it: “I had directed things before in high school, but that’s when I realized, I would love to do this.” NYU was also, she says, a “perfect introduction to New York.” Growing up in a religious family in Maryland, all Headland knew of the city was what she saw in musicals, most specifically Stephen Sondheim’s “Company” (though she maintains that “and another hundred people walk out of the train…” is about as timeless a description of the city as it gets).
While writing plays, Headland interned at Miramax — “the only game in town” — before becoming an assistant. Her experiences there, including a stint as Harvey Weinstein’s personal assistant, inspired her acidic 2012 play “Assistance,” which depicts the lower-rung employees following in their bosses’ toxic footsteps. “I caught some flak because [Weinstein] wasn’t in it,” Headland says with palpable frustration. “I wanted to talk about what I felt like was going on there and what I was experiencing there. I had to do it in a way where I wasn’t going to be sued or slandered.” And so she tackled the industry that enabled Weinstein rather than the man himself. “What I feel is the real horror of that stuff is the environment that’s created,” Headland says. “You can only behave the way that he did if everyone in that company is perpetuating that abuse.”
After five years at Miramax, Headland took a leap of faith and set out on her own. She made her directorial debut with 2012’s “Bachelorette” (based on her play), starring Kirsten Dunst (“the best”) as a terrifyingly efficient maid of honor for a then-unknown Rebel Wilson. Headland wasn’t initially directing the movie until producer Adam McKay asked if she’d like to — and she realized that yes, yes she would. “Even though I’d never been behind the camera, I was like, ‘no one knows these girls better than I do,'” Headland says. “Even if it’s technically not perfect…it would always have that emotional and empathetic through-line.” She followed up “Bachelorette” with 2015’s “Sleeping With Other People,” her whipsmart romantic comedy about dysfunctional friends (Jason Sudeikis and Alison Brie) teaching each other how to love. Headland was then starting to wade into the TV-directing waters when Lyonne, who co-starred in “Sleeping With Other People,” brought her in to “Russian Doll.”
“It came at just the right time,” Headland says. While she’s proud of her twisted rom-coms, the strange, cathartic bent of “Russian Doll” proved a perfect fit for her, an unabashed sci-fi nerd who worships “Star Trek,” Jim Henson’s “Labyrinth” and Stanley Kubrick’s “The Shining.” She’s now hopeful that the Emmy success of “Russian Doll” will lead her to more ambitious projects and help others get their own greenlit. “I love that they’re recognizing this stuff like this weird little Netflix show about female trauma and overcoming it,” Headland says. “[The industry] saying, ‘We are interested in this,’ helps it get into the water supply. And now other artists, whether marginalized or not, can come out and say, ‘We want to get a little weirder.’”