Leslye Headland on Writing, Directing, and Creating


Written by Victoria Myers
Photography by Jacqueline Harriet
April 24th, 2018


In the movie L.A. Story, there’s a billboard along a highway that doles out advice to the film’s protagonist (it was a movie about L.A. in the early ‘90s, and if you were a person watching the film outside of L.A. in the early ‘90s, this all made perfect sense). The billboard’s final line is, “What I really want to do is direct.” Well, easier blinked out in halogen lights than done, especially if you were growing up in the early-mid ‘90s before digital film and before the internet as we know it. In other words, you might end up in theatre school, as Leslye Headland did on her way to becoming a film and television director… and a screenwriter and a producer and a playwright. She started writing plays—her Seven Deadly Sins cycle—as a way to direct (the most famous of those, Bachelorette, was made into a film, which she also directed). Now, the plays have a life of their own. Surfer Girl, set around the sin of sloth, is currently having its New York premiere with Animus Theatre Company in association with The Dirty Blondes. Meanwhile, Leslye is also working on a new Netflix show that she created along with Natasha Lyonne and Amy Poehler. I recently spoke with her about her process for writing Surfer Girl, taking an indirect path to directing, and what it means to be a woman in the entertainment industry in 2018.


Surfer Girl is part of your Seven Deadly Sins cycle. How did you decide to use that as your theme?
As a young writer—meaning this was maybe 13 years ago—I had only written one play and I was really terrified of only having written one play. I had written one play really well, which was Cinephilia, and I thought, “Why don’t you think of it as a big project as opposed to just one play at a time? Maybe do something that could anchor these things.” It was a combination of being bred really Christian and Catholic, and still having seriously practicing Christians at home, and that influence. But also, this was the mid-2000s, so Sufjan Stevens had just come onto the scene and was like, “I’m going to do an album for all 50 states.” That concept of doing a series of work based on a preordained plan was something that was kind of in vogue at the time as well. And I honestly never thought I’d finish them. But what was great about it was once that clicked, I think I wrote Bachelorette in just a couple months. As soon as I knew it was going to be about gluttony, the play just kind of happened. And then, knowing that Assistance was going to be about greed, it just kind of happened. Surfer Girl was around the time where it started to be less about filtering my own personal stuff and more about focusing on the sins. Going like, “Okay, so sloth, okay, that’s weird.” Sloth is like, “Oh, how do you externalize something that’s passive and internal?” That was the beginning of that.

When did you decide on the form for Surfer Girl? Because it’s different than the plays that came before it in the cycle.
Medea Redux by Neil LaBute was a play that we’d done in school a bunch. I had seen it a couple times in school with great actresses like Carmen Herlihy, who did it our junior year and people talked about it forever. My first introduction to that play was seeing her do it, and that was so mind-blowing to me. And then I did a production of Bash in L.A. when I was just starting out as a director, not really writing too much of my own stuff. I thought it was a really fascinating challenge. And LaBute was somebody that I was pretty into at the time, as well, and a form he used a lot was direct address to the audience.

Did the form come before the content, then?
Yes. It started with: I’m going to write a one-woman monologue. And I knew the actor that was going to do it because I was doing the whole series with my favorite company in Los Angeles. The actress that I had done Bash with, Sarah Utterback, I was like, “I’m going to write our own Medea Redux [for her], and then go from there.” I didn’t have something as active as the Medea story. I just had this kind of antiquated, old idea: a sin, quote-unquote.

Let’s talk about how to take something that’s inactive and make it active for the stage. Was the form part of that?
Right. I wish I could say I thought of that, because I think it was actually a good solution. But actually form came first, and then, as I writing it, I thought, “Oh, this is such a great way to get inside someone’s mind.” The climax of the play is when she describes what I now understand to be really crippling depression, but at the time, I don’t think I really even had words for it. The play takes you on this journey with this character over several years and it basically hits this crescendo when she explains what it feels like to feel apathy for someone, and how it’s one of the more terrifying experiences when you suffer from depression or any kind of mental illness. As I was writing it I was like, “Yeah, the only way you can really get the audience to the place where they will be receptive to hearing about that would be to take them on a journey from when a person isn’t that way, and take them from their happier times—or when they’re younger and have more possibilities, excitements, and all that stuff—and then bring them to a place of what it’s like to not have that anymore, and how impossible it seems to get back.” It’s a very hard subject matter, actually. Usually, depressed characters are characters that you feel pity for and that you’re like, “Oh, I feel bad for this person.” It’s very rare that you can watch a story where the hero is someone that’s in depression, because nobody wants to feel that way. Now that I have a little bit more experience, I do feel like something that I really love to attempt to do in my writing is to get the audience to a mental or an emotional state, not so much tell a story. Because the plays, especially in this series, do not have plots. They’re kind of plotless character studies, or like little dioramas that I wanted to create so that everybody would get to a feverish emotional state with the actor, so while they’re all sitting together, they feel that feeling that I have felt in my life that felt so unattainable or indescribable, and everyone feels it together, and then everyone leaves and goes back into their lives and processes that feeling. I feel that is my calling much more so than being a great three-act storyteller.

When you first sit down to write, do you have an image, or do you start with a piece of dialogue? Is there something that is your way into what you’re writing beyond subject matter or form?
It’s usually a feeling that I felt that I’m trying to narratively recreate, because it’s not enough to be like, “I felt this feeling when I was in all these situations,” it’s, how do I create the environment? I usually start with that. It might be an autobiographical thing that happened to me that I’m replaying in my head, and I’m like, “How would a person who doesn’t have any reference to my life or understanding of my personal history, how would I explain this to them without them knowing that I’m explaining it to them?” So it usually does start with that. But a lot of times when I was working with IAMA Theatre Company [in L.A.], because they’re an actor-based theatre company, I would know which actors were going to be in the play ahead of time, and I would usually have one image that I would be like, “Ah! That’s the play.” The play is in that particular image, scene, line of dialogue, monologue, and now I just have to create a thing around that.

What are the other areas of culture that affect your writing?
Music. Even this last play—the seventh play, which I just finished and is going to rehearsals in L.A. in a couple weeks—there’s so much music in the show. Trip Cullman, who’s directed most of my plays in New York, used to joke that staging my plays was like staging musicals. It’s just constant movement and constant set pieces, basically. But, again, none of them move the plot forward, and I think that’s why the work can be frustrating to people at times. I’m a big film nerd but films don’t really inspire me as much as they calm me down. It’s almost like a meditative state of watching.

When you’re writing, do you think of your plays as plays? If you’re seeing it in your mind, are you seeing it on stage or are you seeing them in real time?
I used to always see them on stage, which I think is one of the reasons why they’re kind of the way they are. When I watch Arthur Miller plays, I feel like this guy, he was in their house watching them interact with each other. There’s something about the immersion into that reality that you feel so palpably, and I think my plays are really plays. I would say that with my films, too—even this Netflix show that I’m working on now. In a weird way, they all rely on your own knowledge of other things that are like this for you to enjoy them. I think I’m coming up in that “Ready Player One” generation of everybody knowing all the references, so it’s not fun to put them in anymore, so now I don’t even bother. I’m just like, “This is this story, and I’m assuming you know about all these other things, so I’m going to use a shorthand between the viewer and myself, and just go from there.” They’re very post-post-post-postmodern. They’re not meant to be “real.”

It’s like that concept in literature that literature exists equally, if not more so, in reaction to other literature than it does to life.
Yes, I would say that 100% of almost everything I work on. There’s some very painful personal stuff in all of the plays, but none of them are presented in an autobiographical, realistic way. All of them are played to this very bizarre personal kabuki. I find, too, when I’m writing, that it’s almost like kabuki or commedia dell’arte where each play has the naïve character who’s sort of sacrificed in some way, and then there’s the institutionalized character who’s like, “I’m so entrenched in this ‘sin’ or the way that this is working for me that I’m not going to…” And they’re all me. But that’s not an ex-boyfriend, that’s not my dad—they’re all me, just as stock characters.

One thing I remember very clearly about when I was writing Bachelorette was when Regan, at the very end of the play, says to Becky, “Do you know what people think when they see you on the street? They’re grossed out by you.” I wrote that because that is how, at the time, I spoke to myself. And what felt so odd when the play opened here was the idea that everyone was really taking Regan so seriously as a character saying that to another character and saying, “How could someone be this cruel?” And I was like, “I know they can be because I’m that way to myself.”



How do you feel like your spiritual life affects your work?
I would say that when I started out I was very scared of moral or spiritual arguments. I was terrified of them. It was like running the other way and struggling with my family coming home and having people describe their experiences of praying at dinner and stuff like that. I was so scared. And now I’m a lot more curious and opinionated about it. And I think it’s probably reflected in the work. I would say that the plays move further and further away from punishing you as they move on. They become less black and white and more spiritually gray. So, that’s how I would describe my spiritual life, as just curious. Just kind of like, “I don’t know.”

You’ve been writing for the stage, for film and TV, and also directing, all at once, and for a while now. How has that been? And what has been the biggest challenge for that?
I’m going to answer it backwards, which is that I think in the last three years, since I finished my other film, I’ve gotten more and more into collaborating. Meaning, the Netflix show that I’m working on now, yes, I’m a creator on it, but it’s also with Amy Poehler and Natasha Lyonne. It’s really a concept that Natasha brought to me and was like, “How do we make this a show?” And so it’s sort of becoming a person that, yes, does all of it, but it’s not doing all of it in service of something that’s completely mine. And I’m actually really enjoying that. I really loved doing Frankie Shaw’s show—I did a couple episodes of her show SMILF—and then I did a bunch of episodes of the Heathers reboot for Jason Micallef. And these are people that I’ve known for a long time and I was lucky enough to be around when they got their moment of, “I’m going to make my own show. Will you help in whatever form or capacity that takes?” Having taught myself how to do everything, I felt like I could actually show up and do that. I’m actually really loving it in a way that I didn’t expect to.

Doing it from the ages of from graduating college to 29, those seven years, I think it was just all about practicing, and I didn’t feel like I could practice it until I was doing all of it myself. I’m grateful to have let go of that more and more, but it still rears its ugly head a lot. I’ll be like, “Don’t do it like that. What are you guys doing? Don’t do that. Why aren’t they doing it my way?” I’ve come to the realization that I’m less interested in being Sofia Coppola or an auteur in that old sense of the word, and more of a J.J. Abrams, Ryan Murphy kind of person that’s more like, “There are a bunch of mediums to work in. We can work in all of them.” And what’s tantamount is telling stories and indemnifying women, people of color, queer and trans people. The only way to really enjoy anything you’re doing is to send the elevator back down. Yes, it would be nice to make a masterpiece every time I make a film, that would be something awesome, and I’m sure if I put all of my energy into it, some version of that might happen, but I’m really enjoying working on multiple things at once and interacting with multiple people and indemnifying female playwrights and female filmmakers specifically, but all people that are not white guys. It’s like, “Just go. Do it. You have an idea? Great. We’re going to do it.” I’m just finding it more exciting than trying to do it all by myself like I did when I was younger.

When you were younger and you were first starting out, did you feel like there was one thing that you were most interested in doing, and was that the thing that you felt was easiest for you to articulate and pursue? Or did you feel like you had to do other things and take a more indirect route to doing it?
100% it was directing. When I got to NYU and I took my first directing class, I was just like, “Oh, I’m amazing at this.” I was like, “I love this. I get it. It just clicks for me. I understand it. And I love doing it.” I love actors, I love talking to actors, I love figuring out scenes, I love blocking, I love every aspect of it. I would say the only aspect of directing that I dislike is probably editing films. That’s where you feel extremely lonely and you have your editor, but it’s really just you and the footage, and you’re like, “What did we do?” I feel similarly about writing. I don’t like being alone. I don’t like writing, to be honest. Most of the time when I’m writing, I’m on set or I’m doing something else, because that motivates me and energizes me.

But I loved directing and I was so good at it. I just understood it intuitively. And when I failed, especially in school, I failed big. I would make a huge mistake, huge stuff, and my professors would be like, “You can’t do that,” and I was like, “What are you talking about? Of course I can do it.” Writing became a way to direct, which is not uncommon for a lot of screenwriters and playwrights. Basically, what happened was I got sick of doing Adam Rapp and Neil LaBute things. It’s so different now—you can do a Halley Feiffer play, an Annie Baker play, or a Branden Jacobs-Jenkins play. But I was like, “Oh my God, there’s only so many times I can watch 18-year-olds do Who’s Afraid of Virginia Woolf?” It’s just not fun. Part of Cinephilia was just writing Who’s Afraid of Virginia Woolf? for 25-year-olds because really it’s the same play, it’s “get the guests” but it’s a bunch of shitty 25-year-olds. I guess people call them “millennials” now, right? We weren’t millennials then.

Were you always interested in film and TV?
Yes, from a very, very shockingly young age. I never thought I would actually make films, though, and I think part of that is the lack of representation of filmmakers. I just assumed it would never happen, to be honest, so when it finally did, I just couldn’t believe it. The whole time I was just pinching myself.

Was that part of the reason you studied theatre at NYU instead of being in the film school? And was part of it also a feeling of that you almost have to be invited to the film and TV world through theatre?
100%. It’s also so different now. I was there right at the cusp of digital, so there was not that sort of surge of mumblecore [filmmaking]. That was just starting to happen when I graduated. Also, the people that I knew in the film school, when I talk to them about it, it didn’t seem to be that they were learning that much about storytelling; they were learning about film like montage and all the technical things. What was amazing about Playwrights Horizons was that Playwrights taught me how to put something together, which I found infinitely more useful than knowing which lenses to use, because I can just ask my DP [Director of Photography], “What do you think? Thoughts? I want it to feel like this thing.” Now I have enough experience that I can be like, “I think we should use this lens on this, and I think we should do this kind of coverage.” I have enough layman knowledge to be able to dictate particular things, but Playwrights taught me how to talk, to design and build, “I want it to feel like this, but I want it to look like this.”

People talk so much about “mentorship,” which is a term that I hate, but for lack of a better term, did you feel like you had that or did you feel like a lot of what you were doing you were teaching yourself?
I had a lot of support but not a lot of mentors. A lot of peers supported me, and IAMA, for example, was like, “We’ll do anything.” But I found myself kind of consistently disappointed in my mentors because they were all men who were kind of shitty. I think that’s why I crave it so much now with my assistants or my writer’s assistant on this show. I’m like, “Oh, let me explain to you what this thing is, or what we’re doing.” Nobody did that for me. It was always either this trial by fire or white guy weirdness, where I was like, “I’m not here to hang out with you. I’m not here to pump up your ego about what’s going on. I’m actually here to learn, and to get better, and to get better than you. So, if you’re not into that, or if you’re threatened by that, then we’re going to have to move on.” The people who have really inspired me the most are my peers. The feedback that I get from the women that work for me is invaluable to me. I hope that I’ve created an environment where I’m like, “You can tell me it doesn’t work.” I want to know it doesn’t work. Whereas most of the men that I worked for when I was coming up, it was this terrifying idea that, “Oh, I have to make feel everybody feel better or they’re going to fire me,” which is not mentorship. It’s just not. I don’t know what that is.



I was reading a bunch of interviews you’ve done in the past and I saw that you got asked a lot about likability and female characters because of the subject matter of your work and how people view it. The fact that you’ve had to have that likability conversation so intensely and about your work, has that ever affected how you view yourself and how you view yourself when you’re in a position of authority?
Certainly. I can’t tell you many times I’ve gotten feedback from a producer that’s like, “You need to bring it down.” And I’m just like, “What?” First of all, I’m not abusing anybody—I’m not actually doing anything wrong. One thing that I love answering—although I don’t know if it gets printed that often—people are like, “What’s it like being a woman on set?” I think they want to hear a story where I get catcalled by the crew, or when the crew doesn’t do something. Honestly, the way that I think I get treated differently as a female filmmaker and showrunner is that men feel like they’re just allowed to take up all the space. I can’t even imagine a woman that’s playing a part who would be like, “I’m sorry, we need to stop everything. I’m going to take up 15 to 20 minutes of your time to have you walk me through what the fuck is going on” [as men do]. And then if I react with, “Absolutely not, I’m not indemnifying this behavior and we’re moving on. And respectfully, I hear you, but it’s my show and I think we’re good, so I’m sorry that you feel that way but you need to move on,” it’s like, “You should really work on your bedside manner right now.” I think anybody that has worked and done as much as I and so many women have, they don’t need to say things with a sweet face on. It’s like that famous Nicki Minaj meme where she’s like, “You’ve gotta be good at what you do, you gotta be sweet, you gotta be…” And then she’s like, “I can’t do it all. I’m a human being.” There’s this lack of space for us to just be human at our jobs. It’s changing and it’s changing in my lifetime, which is kind of fucking amazing to say. But there’s that idea that a female heroine, or that you as the director, have to do everything that a man would do in this situation, but do it with makeup on and a smile and be thin and make everybody feel good… it’s just crazy.

The entertainment industry is an area where there’s a lot of gray in terms of behavior and not really one where you can afford to be a moral purist.
I would agree with that.

How do you find the balance of making choices where you like the work, you feel like it’s contributing good, but also being in an industry where, again, moral purity just is not really an option all the time?
Someone gave me such a great compliment on this. An actor gave me such a great compliment through my wife, who’s on the show. She was like, “What I like about Leslye’s brand of directing is that she is not afraid to say, ‘I don’t know. I don’t know what this is about, let’s figure it out. Or, let me think about it and I’ll get back to you.'” And I think that something that doesn’t happen a lot in this industry, and I actually try to do that much more so now than I did when I first started. Again, I was working under a bunch of men and it felt like weakness was not acceptable. Now, what I do is I apologize. If I do something and later I’m like, “That might have been inappropriate, actually, that I said that,” I either write somebody an email or I sit down and I go, “When I said that thing, or when I snapped at you, I really want to apologize because you’re doing a great job and I think that I was reacting very emotionally in the moment, because I’m stressed out. It’s not really an excuse, but just know I appreciate the work that you’re doing and please don’t hesitate to let me know if I say something or do something that makes you feel uncomfortable.” It’s really that simple. That’s the thing that I think is so fucking mind-boggling when you think about kind of how fucked up everything can get: that really a simple face-to-face apology or a face-to-face conversation can go so far for people. The idea that a director, a showrunner, or a playwright can’t apologize, can’t show that they’re a human being and go, “I failed in this moment and I should have been better or I should have X, Y, and Z’ed,” I think is just so detrimental to the whole artistic process. And that’s what I think can help with navigating the gray is if you’re just like, “Oh, you know, I can tell that that upset her, let me go to talk to her—or him, or whomever.” I don’t think that makes me weak. I don’t think that invites disrespect. I think people really respect that.