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An Irreverent Playwright Turns an Airport Encounter Into a Psychological Thriller


It’s hard to imagine Leslye Headland, the 35-year-old scribe behind Second Stage Theatre’s brutal new play The Layover, in an airport. She seems to belong in a crazier place: an occult noir sex party straight out of Eyes Wide Shut, maybe, but with more laughs. An airport terminal is too banal, too mundane, and Headland doesn’t do mundane. She doesn’t do Cinnabon. She doesn’t put her seat-backs and tray tables in their upright and locked position.

“Layovers are very boring,” she agrees, with a laugh, sitting at the theater’s café. Headland — whose work over the past decade, from her “Seven Deadly Sins” plays to her sex-addict screen comedy Sleeping With Other People, has established her as one of the most offbeat theater and film writers working today — has the sort of personality that fills up the whole room: She’s gregarious and uninhibited, the kind of presence that demands extra legroom.

Still, an airport terminal — and the vertex between what’s “crazy” and what’s “boring” — is exactly where The Layover begins. Two strangers, Shellie (Annie Parisse) and Dex (Adam Rothenberg), meet while stranded in a pre-Thanksgiving airport layover and start a combative conversation about the expectations society forces on women. It’s a wide-ranging discussion — sometimes tense, sometimes flirtatious — that flits from holiday plans to how to get away with murder. The encounter spawns a series of unpredictable, disturbing events, and as emotions spiral uncontrollably, the play’s overarching question crystallizes: Is it ever possible to really know another person when there is so much we hide from ourselves?

The concept of strangers meeting on a train (or, in this case, a plane) has long fascinated Headland. A decade ago, she started talking with her seatmate on a flight from Los Angeles to New York. It was one of those conversations — not awkward chitchat about in-flight entertainment options or the weather, but a visceral connection that made the hours disappear. It was only when their plane began its descent that he abruptly announced that he was just a few weeks away from the altar.

“How many different things had to line up for that conversation to be as stimulating as it was?” Headland asks, still fascinated by the memory. “I thought: Here’s a person that I could connect with, but am never going to connect with. It’s definitely something that I never forgot.”

It’s clear she’s injected some of these preoccupations into her latest project. Directed by her longtime collaborator Trip Cullman, The Layover explores richer, more complicated emotional territory compared to Headland’s earlier and more youthful and overtly comedic work — an oeuvre she’s built since graduating from New York University’s Tisch School of the Arts in 2003.

While Headland’s earlier characters leaned forward into future mistakes, the world-weary characters in The Layover look back on ones they’ve already made. “When this script came across my desk, I fell madly in love with it, immediately,” says Cullman, whose partnership with Headland began by chance.

“We were sort of put together in a shotgun marriage on her first play in New York,” he says. “Like a percentage of arranged marriages that are successful, it was a wildly successful pairing. We hit it off immediately.” That first play was Bachelorette, one of Headland’s “Seven Deadly Sins” plays; it explored gluttony through the lens of self-absorbed twentysomethings on the eve of a swanky wedding. The two also worked together on Assistance, another play in the series, which loosely used Headland’s years as an assistant to Harvey Weinstein to examine corporate greed.

But the new play ventures into deeper psychological terrain that portrays the call-and-response of sexual desire as shaped by society and upbringing, in often frightening ways. “[The Layover] is a real departure for her because it’s about adults. It’s very darkly funny, but at the same time it’s also deeply disturbing — almost like a thriller onstage,” says Cullman, with obvious enthusiasm.

He’s right: The Layover works the suspense almost painfully well. From the moment Dex asks Shellie, a professor of American crime novels, to describe her idea of the perfect murder, the simple question hangs over the rest of the play like Chekhov’s gun — a weapon that, once introduced into a dramatic work, must fire. In Headland’s hands, the theater becomes a Möbius strip of manipulation: The people onstage are being played, but so are those watching. It’s a deliciously twisted game.

“I guess I do mess with the audience,” admits Headland. “I would rather break your finger and reset it in ninety minutes than congratulate you on having working hands. If I’m going to make art, I want to do stuff that’s going to leave a scar.”

That’s something fans of her film Sleeping With Other People, which she wrote and directed, will remember. In it, she set two sex — or is it love? — addicts, both with breadcrumb trails of broken relationships behind them, against each other. But the film’s sharp edge, like that of her theater, has a dark political consciousness that distinguishes it from other raunchy comedies: In one scene, serial womanizer Jake tries to convince his girlfriend that she’s only upset he slept with her best friend because of a cultural pressure that turns women into rivals. Perhaps unsurprisingly, Headland once described the film as “When Harry Met Sally… for assholes.”

Asked about her predilection for unlikable characters, she says, “I actually really like [my characters] and identify with them…. I think because I’m always thinking on that macro scale, the micro scale of the emotional violence doesn’t really hit me until it’s happening.”

In The Layover, she takes it a step further. We see this quality most obviously in Dex, who goes obsessively in search of Shellie after their initial encounter, but also in Shellie’s reactions to his overtures, which shed harsh light on the difference between how men see women and how women see themselves. The characters’ increasingly tense interactions — and in particular, Shellie’s growing unease — illustrate the kind of teetering balance the play manages to sustain: between cynicism and hope; fantasy and daily life; cinematic gestures and harsh truths.

Headland says her feminist perspective demands these incongruities: She can’t describe the internal experience of being female without engaging the larger question of being a woman in the world. “[The Layover] is a deeply feminist play,” says Cullman. “I think certainly it’s about sexual obsession, but more specifically about the ways in which we live in a patriarchy and women get trapped in roles that are determined by men.”

Given the messy tangle, a particular strength of the play is how open-ended Headland is about who is to blame for what; it’s an outlook that may have something to do with the playwright being, as she puts it, “breast-fed” C.S. Lewis’s theories of morality as a child. “My job is to show you a crooked line,” she says, “so you can tell me what a straight one looks like.” Will the characters get what they deserve? Does life, like theater, have a playwright to oversee the arc of the story and promise a “perfect punishment” for all?

“I don’t know if it’s true that punishments are always perfect, but I do love that someone says that [in this play],” says Headland, chuckling. “I am the God of my play, but the audience is the God of the experience of my play. I have never felt a duty to make everyone feel the same way. The big question is: What does this make you think?”