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Leslye Headland Writes Bad First Drafts, Too

A blonde woman wearing a black turtleneck poses for a portrait.
Photo-Illustration: by The Cut; Photo: Yulia Reznikov

Cult of Love was the last play Leslye Headland wrote for her Seven Deadly Plays cycle but her first to make it to Broadway. The starry production, which features Shailene Woodley and Barbie Ferreira making their Main Stem debuts alongside pros like Zachary Quinto and Mare Winningham, has earned raves for its blisteringly funny take on the family-reunion drama. Headland began writing it shortly after the first Trump election and didn’t know how it’d be received. “I worked on this play for eight years, so there’s all this pressure,” she says.

But the writer-director likely had nothing to worry about. Since its initial 2018 staging at Los Angeles’s IAMA Theater (where she developed other works in the cycle, including Bachelorette, which she later adapted into the Kirsten Dunst movie, and Assistance, about her time working under Harvey Weinstein) Headland has experienced her share of mainstream notoriety. She co-created the much-loved Russian Doll series with Natasha Lyonne and Amy Poehler and helmed the mega-budget Star Wars spinoff, The Acolyte, which drew the requisite critical praise and neckbeard ire faced by women in fandom fields. Headland credits a lifelong ability to be proud of her work, and especially the support of her wife, the actor Rebecca Henderson, who stars in Cult of Love, for this heady phase of her career. In this final week of performances, Headland announced she’s adapting the play for the screen. She lives in Brooklyn with Henderson and their young daughter. Here’s how she gets it done.

On morning priorities:
I wake up at like 6:30 to 7 a.m., because I have a 19-month-old. I warm up her milk and then I go see her and she says, “Hi, mom. Hi, mom.” She drinks her milk, we snuggle. She plays and shows me her stuffed animals and we all give kisses: I give kisses to the penguin, she gives kisses to the penguin. It’s a wonderful way to start the day and remember that, as much as I love writing, there are things in the world that supersede that. Writing used to be the only thing I would think about, especially if I was on a roll the day before. But since my daughter’s been born, I don’t really feel that way. The switch to working is so much easier. Her nanny comes and takes her to school around 8 a.m. and that’s when I go to my office in Tribeca.

On staying on task:
I use the Pomodoro Technique: I set a timer for 25 minutes and write for 25 minutes straight, then have five minutes off. Sometimes I take longer than five minutes, especially if I’m really struggling, but I try to get eight sessions in the day. It usually ends up being like five or six. I think, write the bad version of the scene. Don’t stress out about making the scene extraordinary. You know what the scene needs. You know where it’s supposed to go. So just write the bad version of the scene, where some of the lines are quotes from other movies. When I first started writing plays with IAMA, there were just deadlines. I would have to get something done by X-date so that we could start prepping the next show. That was a little more about getting things done, versus spurts of inspiration or energy.

On writing “the bad version”:
The characters have dynamics already; they almost always come first. I think the exception would be Cult of Love, because that has such a complicated structure. It started with, “How do you convincingly do overlapping dialogue that isn’t frustrating for the audience, but feels like people talking in a room the way they actually talk?” That’s probably the one exception. But everything else starts with, “This woman, this woman, this guy, this guy.” Sometimes something will just come to me, like in Cult of Love, the father has this long monologue about love and how it supersedes everything. I was writing the bad version of the scene, but when I got to that moment, it just came out and I never rewrote it, ever. It just flowed. That happens 10 percent of the time, maybe 5 percent, and typically it’s when the character is at the apex or nadir of their journey. Usually I go back and I rewrite. I love rewriting. First drafts are the worst. Once I have a semblance of the script that I’ve rewritten a couple of times and improved, that’s when I start doing readings. I call my friends and say, “I need to hear this out loud, would you be willing to come and play this part?” I have to hear it out loud, and then that’s when I furiously rewrite. You have to start working the dialogue in a way that feels natural.

On the Seven Deadly Sins:
One of the first things I thought about when writing about pride for Cult of Love was a pride of lions. It felt like it was going to be a family play. With every sin, I really try to think about how to flip it on its head. Like gluttony for Bachelorette: Those girls are just ravenous for so many things and will not stop until they’re destroying themselves, which I think is what all of these sins are about. They’re not about morality. They’re about how those concepts are connected to self destruction.

On trying to set boundaries:
It’s a little easier to cut off my availability now with the baby, because I’m home for bedtime. But it is difficult to have that boundary when Zooms happen at the last minute and it’s like, “We all need to talk, we want to get this done before the weekend.” It’s not negative, it’s just difficult to navigate. I usually take the subway, but sometimes a call will happen and I’ll take an Uber.

On the people who help her get it done:
I have an assistant who lives in Los Angeles. I would say a good percentage of her job is scheduling and coverage. Because I used to be an assistant, I’m a little morally opposed to an assistant doing personal things for me. I just don’t think that’s their job. So I have her, and then I have a very, very, very part-time assistant who helps with more of that personal stuff, probably twice a month. Like, “Oh my God, this thing happened, can you pick this up and bring it over?” But my salaried assistant is not somebody who is supposed to do that stuff.

On leaning on her partner:
It’s worth saying that the secret to success in our industry is having a wife. That’s why it’s all men succeeding, right? Because they have somebody who’s emotionally and logistically supporting them all the time. I don’t mean to be gendered, though, it’s a little more nuanced than that. I mean any partner supporting you in that particular way. I collaborate with my wife creatively a lot. She performs and acts in a lot of my work, all the way down to reading the script and giving me notes before anybody else sees it. She’s in Cult of Love right now. But when I see men doing project after project, the way that I attempt to do, I’m just like, there’s no way you’re doing that without emotional and logistical support. There’s no way. That’s why you see so many men succeeding and why, when they don’t thank their wife at award shows, I’m just like, tsk tsk.

On feeling like she’d “made it”:
We did a workshop of my first play, Cinephilia, which was “lust.” I must have been 25 years old, and I thought I had written Who’s Afraid of Virginia Woolf? I was going to be the next great American playwright. Eugene O’Neill? That’s … who I am. We did this hybrid workshop performance and, within five minutes, the audience was laughing. They kept laughing and I was shocked that people were laughing. I just couldn’t believe it. However, in that moment I thought, This is the type of writer I am.

On protecting her work:
The way I describe my last play, Reverb, to people is “Fight Club: The Love Story,” and I got a review that said it’s really hard to care about people who are this fucked up. That fucked with my head. I don’t feel that way about my characters. The same thing happened with Bachelorette, the film. When I was going around having generals with people, one person said a similar thing that rattled around in my brain: “This is how women talk, but this is not what women want to watch.” That messed with me because I thought, “But this is what I do …” Obviously it’s just one person, but if people feel that way about my work, it’s a setback because I’m like, “It’s not going to work, it’s not going to make money, people don’t want to watch that. I guess I better pack up and get out of here.” I go into a real steeling-myself, introverted space. I put my walls up and lock my heart into a safe that nobody has the code for. And I just keep moving forward because I have to protect the play. That’s what’s important, not me. I have to push out whatever personal reaction I’m having and just go. The piece has to come first, as if it were a child.

Leslye Headland Writes Bad First Drafts, Too