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Leslye Headland on Russian Doll, Her Harvey Weinstein Play, and Why New York Is a ‘Graveyard’

Photo: Astrid Stawiarz/Getty Images

The story behind Russian Doll largely comes from the life of star and co-creator Natasha Lyonne, who’s said that its Groundhog Day premise and New York sensibility are adapted from her life as an artist and addict. But when Lyonne and co-creator Amy Poehler began developing that idea into a TV series, they brought on writer, playwright, and Bachelorette director Leslye Headland, who helped shape the actual narrative driving the critically acclaimed Netflix series. (Headland, credited as the show’s third co-creator, directed four of its eight episodes and co-wrote three.)

When Vulture spoke with Headland earlier this week, she was walking through New York to meet up with a friend. She spoke in detail about the process of developing Russian Doll, its visual references to “tough-guy ’70s movies,” the show’s special ties to Tompkins Square Park, and the possibilities of a second season. Headland also talked about her 2008 play Assistance, which she wrote after spending a year as Harvey Weinstein’s assistant, and why she’s not interested in David Mamet’s Weinstein project.

I want to talk about the genesis of Russian Doll, but first, have you seen this theory from Jason Zinoman about the show as a meditation on the Tompkins Square riots and the loss of bohemian New York?
Oh my God, Natasha’s gonna freak out. No way. I have to send that to her. Oh my God, she’s gonna lose her mind.

So the riots were in your heads as you wrote the show?
Absolutely. Natasha has lived in that area and has lived in New York so much longer than I have, and even before I came on to the project, it was going to take place in and around Tompkins Square Park. New York is kind of this place that, I don’t know how to put it … when I think back on it now, I do remember talking about how New York is kind of like a graveyard. We’re all living in a graveyard. I remember we started talking about real estate in New York and it being haunted, and then people being haunted …

I’m not doing a good job of answering your question, but the quick answer is yes. We are haunting not only the artists that came before us, and the people that lived and died in this city, but we’re also chasing our old selves. For me, that area really recalls when I went to NYU and when I first moved to New York, which is like late ’90s, early 2000s, and 9/11 and all that stuff. I definitely walk around that area and almost expect to run into my 19-year-old self. Because I feel like she is still here somewhere, I just don’t know where.

Natasha Lyonne and Amy Poehler had been developing the show for a few years before you joined the project. Where was it when you came in, and how did you develop it from there?
A lot of the characters had already been created. They were all these downtown archetypes that Natasha had either created or had met in her life, but I wouldn’t say they’re based on real people. When she would talk to me about them, I saw them much more as totems of her mind. So my way into it, initially, was thinking of all of the characters as part of Natasha, and by extension Nadia’s character.

Tash and I met up every few weeks and we would work. It’s chop wood, carry water stuff — we had to start making decisions, we had to figure out “the rules,” all those things. Really what I brought to it was, I’m a taskmaster. I definitely have that air about me of like, Okay, but what are we going to do? So that’s my major contribution. But I learned so much by osmosis of being around [Lyonne] and her brain. That was always the most interesting part of the show to me — the things that she found interesting, the parts of the human psyche, New York and life and lessons and all of those things, it was always coming from her. And I was going, Okay, I think this is how we can get the audience to feel that way. I think this is how we might be able to structure that.

I was joking to another writer that I’m developing something with, I was like, “You’re the medicine, and I’m the gel cap they put the medicine in.” If we do our job right, no one should even realize that it came in a gel cap.

The gel cap is really important! If it’s not there, no one’s getting the medicine.
That might be giving myself a little too much credit, but I guess that’s a good way of describing what I think my strengths are.

You also directed four episodes of Russian Doll, including the first one. That’s more than being a gel cap, right?
Yeah, I guess so. I put together a little look book of images, and it was all the films that Natasha and I had wanted to emulate and recall for the audience. We were like, “We would love to have The Long Goodbye but with a female protagonist.” Those tough-guy ’70s movies, why don’t they have any lady main characters? Those are the movies that Natasha and I love. All That Jazz was a movie where, right away, Natasha knew she wanted [Russian Doll] to feel like that. Even before we broke in the story for the pilot, she was like, “I want this to be All That Jazz. I want this to have that same energy, that same level of heartbreak.”

So it really is a testament to the clarity Natasha came to the project with. And also the willingness of all the department heads — like Jenn Rogien our costume designer, and Michael Bricker, who built that enormous, gorgeous set that’s Maxine’s apartment. Not to mention all the stunts done by Becca G.T. Then our hair person had to make a perfect wig. I kept saying, “The thing that will sell this is if her wig is perfect.”

That wig is very persuasive. Speaking of it, I loved the shot in the last episode where two Nadias walk past Natasha during the parade. That was also the wig, right?
Oh, yes. We dressed two other actresses like Nadia and then walked them toward her.

Photo: Netflix

Can you tell me the idea behind that moment? In my head, it was multiple timelines converging, but I have to imagine there are other readings too.
That’s a good reading. I mean, I can definitely speak to the fact that a lot of different endings were pitched. We thought about a lot of ending moments and it must’ve been Natasha that pitched the parade thing — what are they called, those puppets? [Ed. note: Bread & Puppet Theater.] There’s something Fellini-esque about an ending like that, where we’re acknowledging the artisanship of the show. You’re not breaking the fourth wall, exactly. But this is how I feel when I watch the ending of 8 ½ and the ending of La Dolce Vita.

When I was in theater school at Tisch, there was a big trend of the student directors not having curtain calls. It was a big thing, it was like, The show’s over and then the lights just come up! And the audience has to sit with it. One of our professors sat our year down and was like, “Guys, let me explain what a curtain call is. It’s not about you. The point of this is that you stand in front of the audience and you apologize to them for not getting real life right. You are bowing to them in deference to whatever it was that happened within their minds, because they are part of that story as well.” I don’t know if that’s what the ending of our show is, but that’s what it reminded me of. I was like, Oh yeah, it’s a curtain call. But as far as what it means for Nadia and timelines and season two, I cannot speak to that at the moment.

But I have to ask: Russian Doll was a three-season plan, right?
Yes, we pitched three seasons when we did the pitch back in the day. But not even being coy, no one expected this season to become quite what it was. It went places that were even more unexpected and exciting than we initially had planned. I don’t know if it necessarily means we would go with that original plan. Or maybe we would — I don’t know, we haven’t talked about it yet. We’re still reeling. I’m just so shocked that people really personally relate with this.

Art being personal to the people who made it almost always manages to communicate something universal. The show does that really well.
Thank you. I’m not trying to be cute, it’s just that I can’t really say. We did our due diligence when we started this journey, but we didn’t assume we’d get a second season, to be honest. We definitely went in planning on it, but once we made it, we were like, “We have to send this out into the world as its own thing.”

I have to ask you about a very different topic: Terriers. I loved that show. It was your first TV staff writing credit, right?
Yeah. It was my first job, honey! It was my first fucking job. I will never forget that day. I was sleeping on someone’s couch and [series creator] Ted Griffin fucking called my cell phone and was like, “Hey, you’re hired.” And I was like, “What!?” I even joked to him, “You know I’ve never done this before, right?” And he said, God bless his heart, “Neither have I.” I will never forget where I was standing when I got that call. I was like, “Oh, I’m a writer. Fuck.”

Terriers is so different from the projects you’ve done recently. Is there still appeal for you in a show like that?
Oh my God, yeah. On the surface, it’s not very much like my stuff, but I really related with Hank’s alcoholism. Addiction is a theme that I always come back to. To me, Hank’s entire through line could be traced back to the fact that he was a drunk not drinking. When I was reading and watching the pilot, I was like, “Yeah, I’m attracted to stories about people who have created prisons for themselves and are trying to get out of them.” I think I’m always gonna be attracted to stories like that, whether they’re male protagonists or female. I certainly do love my female protagonists a lot, and it’s really, really fun to write them and see them out there in new, different ways that maybe they haven’t been yet.

What did you learn from Terriers?
It was fucking rad. I love Tim Minear, he’s basically one of the greatest writers living and working. He taught me so many things. He also was the first good boss I’ve ever had. You know what I mean?

I do.
All the guys on the show were great — Ted and Shawn [Ryan] and all those guys — but there was something about Tim. He was hard on me in the right way. I had been so used to verbal abuse and being run by fear and fear of failure, if not fear of punishment. Tim was the right amount of, “You need to do better, but that doesn’t mean that you’re failing.” He made you want to be a better writer. You wanted to be like, “How do I impress Tim? How do I make Tim laugh?” But not in this scary, fearful way that I had been used to.

Speaking of the scary, fearful way: Have you seen that David Mamet is staging a new play with John Malkovich about Harvey Weinstein?
I did.

What do you think about that? About a year ago, you wrote on Twitter, “A Broadway producer shouldn’t be asking an old white guy who doesn’t believe rape is a thing to write a play about Harvey Weinstein.”
Wow, I was really dragging Mamet there, wasn’t I? Oh God.

You also said that you wished they would revive your play Assistance, or at least a show written by a woman.
No one has to produce Assistance. That’s certainly not my feeling about it. It’s more that I would be more interested in a female playwright’s take on this, number one. Number two, one of the main criticisms that I got when Assistance went Off Broadway was that I didn’t show the boss. It was basically, “Why would we wanna watch Devil Wears Prada without Meryl Streep?” The point of the play was that the power the abuser has over you doesn’t have to do with their physical presence, as much as what they’re doing to you mentally. Of course, physically as well. However, I think what was interesting was looking at how abuse cycles and trickles down throughout a culture and a company. We were like, “You cannot give him any sort of a platform when you’re telling the story of the people that are either working under him or his victims.”

That was just my feeling on that particular play. I’m certainly not trying to drum up interest in that show. It’s more that I’m like … listen, that was the play people wanted me to write at the time. They wanted me to put him onstage. They wanted me to say all these things that I couldn’t legally say. I guess that’s interesting, but I would rather see Sarah Ruhl, Halley Feiffer, Jocelyn Bioh’s version of that, instead of David Mamet’s, truthfully. But sure. Do what you gotta do, guys.

I also wanted to ask about one of my favorite lines of dialogue from Russian Doll. It’s in the last episode: Those stupid Wall Street bros are in the deli, and there’s this background exchange where one guy says, “You both have coke guys?” Another guy goes, “Yeah, don’t you have a coke guy?” And he says, “I am a coke guy.” It was so perfect.
Oh my God, I love that. I don’t even remember that. Natasha is an incredible actor on top of being an incredible writer and director, so you would get to a point where you’d say, “Okay, is there anything else that we should try here that we haven’t done yet? Is there something that you wanna put your own spin on?” We did that all the way through the show, including and up and into ADR [additional dialogue replacement], so that line I’m sure is an ADR line.

One of my favorite jokes is an ADR joke: “Remember littering?” We were in an Uber and Natasha was like, “Remember littering?” I just died laughing. My coffee just went everywhere.

It’s a perfect Tompkins Square Park line.
She was like, “Remember when you could just eat a piece of pizza and throw the plate out the window of the cab?” If you lived in New York in the mid-’90s, you were just throwing shit everywhere. I remember doing that. I’d finish a beer on the street and just throw it at a car. We were insane. We were just fucking crazy.

That New York is gone now, right?
Yeah, but is it? It’s still lurking among us.

Russian Doll’s Leslye Headland on Why NYC Is a ‘Graveyard’