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Leslye Headland
Photograph: Robyn Von Swank

Leslye Headland talks about selling out, good directors and The Layover

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The way Leslye Headland talks about her collaboration with director Trip Cullman, you'd think they were a couple. They met on 2010's Bachelorette when Second Stage Theatre set them up on a "blind date," and their "lovefest" continued on 2012's Assistance at Playwrights Horizons. (Bachelorette is actually scheduled for a revival at Tribeca's Walkerspace September 8-17). Now they're back together for Second Stage's The Layover, and the so-called raunch-com queen (a title earned for the hilariously informative fingering tutorial in her 2015 indie flick Sleeping with Other People) doesn't hold back. "If I were to ever actually be with a male partner it would be Trip," she confides with a cackle. "He won't have me, but I would be 100% interested." No wonder Headland has romance on her mind since The Layover tracks the life-altering relationship that develops between Shellie (Annie Parisse) and Dex (Adam Rothenberg), two strangers on a plane. But, like the Hitchcock film and Patricia Highsmith novel of a similar name, this initially lighthearted pairing belies a sinister undertone.

Even though The Layover goes in a wildly different direction from Sleeping with Other People, both couples reminded me of each other.
This play is sort of like a companion piece to the movie—the more upsetting version! Dex and Shellie and [Sleeping's] Jake and Lainey are sides of a similar coin. They represent different meditations on the same themes of loneliness, how bonds end up popping up between us without us even realizing it, and how weird and exciting and enigmatic that can be. Like James M. Cain said, “That's all it takes, one drop of fear to curdle love into hate.” You really only need to change a few things to switch genres when love is involved. There are just a couple of things that end up pushing this into the super creepy instead of the super romantic.

The Layover doesn't go where audiences expect, so I don't want to give anything away. However, I noticed that, like much of your work, this too has an impending wedding.
My DP [director of photography] for Sleeping was like, “Wow, both of your films end with weddings.” And I was like, “You know what else always ends with weddings? Shakespeare, you fucking asshole!” I get very baseline when it comes down to how I bring my characters to a conclusion, because I do think that there are only three endings. I don't really come from a place of let's reinvent the form. I'm more interested in the moral ambiguity and nebulousness within genres. With Dex and Shellie, it isn't clear who's the bad guy and who's the good guy. There's an inevitability to Dex and Shellie's coupling that feels extremely romantic but there's also this sense of underlying violence that exists in every relationship, the same way there's an underlying rom-com in every relationship. It just depends on which way you want to look at it.

This is your third play with director Trip Cullman. Why does your relationship work so well? 
My plays are deceptively difficult to do. At first they seem like these kitchen sinkish dramas, like we're not reinventing the rules of the space or doing anything crazy. Yet they're pretty hard to nail down in terms of tone. Trip's the kind of director that doesn't need to put his own thoughts on top of the play, he just wants to execute it to the nth degree. And that's really important for my stuff. What's also nice is that he's “fluent in Leslye” and has really good taste, which I don't think I have. I steal a lot from him as a director. I don't know if I would have made two films without having worked with Trip first to be honest. I studied directing in school but he taught me how to run a room and how to be diplomatic. When I was young, I thought being diplomatic was like giving up, you know? Like if I took somebody's note that meant I was a fucking sellout. 

Bachelorette and Assistance were part of your Seven Deadly Sins cycle and represented gluttony and greed respectively. (The Layover stands alone.) You only have one more sin to go: pride. Why did you save it until last? 
I feel like all of the sins lead back to pride, which is one of the reasons I've been actively procrastinating writing the play. It's definitely the one that's hardest for me to wrap my head around. Pride is a tricky thing. People think of it as having a big ego or something like that, but my version of it is that I'm the biggest piece of shit at the center of the universe, the high highs and the low lows of self-involvement. I would say that's my biggest sin, being a little too interested in myself. Whenever I do get around to finishing that script I think it will be fun to tackle but also hit a little too close to home. 

You've written and directed two movies and done some TV work, yet you always come back to theater. Why? 
Theater is where I grow, for better or for worse. I don't know if every play I'm ever going to write will be that great to be honest. But theater is where I developed as an artist. Oh God, I say the word “artist” and I just want to die! The playwrights I was always super interested in emulating were like Mamet, LaBute, Adam Rapp, Sorkin and Kenneth Lonergan. These guys all work in a bunch of different mediums and direct their own work. I'm grateful I ended up getting a chance to do all that stuff, too. I guess I am surprised, too, only because I'm a chick, so that doesn't usually happen. 

The Layover is at Second Stage Theatre through Sept 18; Headland's Bachelorette will be revived at Walkerspace Sept 8–17.

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