It's Not You, It's Me: Interview with 'Sleeping with Other People' Director Leslye Headland

on September 11, 2015


by Daniel Loria

Bachelorette's legacy in the film industry is tied more to its much-touted success as a VOD release than to its own merits as an ensemble comedy written and directed by a first-time filmmaker. While it's not unheard of for a film to find its audience away from theaters --Fight Club and The Big Lebowski come to mind during the DVD era-the VOD angle in the conversation around Bachelorette overshadows an edgy film that signaled the arrival of an exciting new voice in comedy, Leslye Headland. After tackling the screenwriting duties for the 2014 remake of About Last Night, Headland returns to the director's chair with her latest comedy, Sleeping with Other People. The film pairs Alison Brie and Jason Sudeikis as recovering sex addicts whose platonic friendship acts as a de facto support group as they try to establish a semblance of order and stability that's been missing from their lives. BoxOffice spoke with writer-director Leslye Headland about her process, her own love-hate relationship with New York City, and the opportunities (or lack thereof) available to women in independent film.   

This is the first of your films that isn't based on one of your own plays. Did it change your process significantly to tackle a project as a pure screenplay? 

Writing it was easier, actually; adapting Bachelorette and About Last Night was a whole other process of asking yourself what type of movie your characters want to be in and updating the material so it feels natural and exciting as a screenplay. It was easier to come from a place of nothingness; even though it was a little more daunting in the beginning, there was a little more freedom to create a brand-new story with new characters. The characters in Bachelorette, for example, already come fully formed and are just looking to talk and scream at each other. It was also a bit easier in terms of directing; it was nice not to have anything hanging over your head, thinking you have to fulfill the promise of something else, that it can just be its own thing.  

Working in theater, you have the benefit of testing out jokes in rehearsals and with live audiences. How was the workshop experience different with this script?  

It definitely starts with the characters, but the whole workshopping aspect still exists in film when rehearsing with the actors. I like to do a reading of the entire script with them and look at every joke in every scene to see how they work with the characters. Then I go back and do another pass. Working with my producers Gary Sanchez, Jessica Elbaum, Adam McKay, and Will Ferrell and talking about how to properly direct improv and how to get the most out of every joke in every scene, we end up looking at scenes in screening rooms with anywhere between 15 to 35 people, where we get to see which jokes are landing and what is getting the biggest laughs. So it's not too different, actually; it's just a different order of events from what you go through in workshopping a play.  

One of the aspects I liked most about your new film is the way you use New York City. There's always something vaguely foreign to me about Woody Allen's or Martin Scorsese's New York; Taxi Driver and Annie Hall were only released a year apart, and their stories are set 20 blocks apart, but it's like I'm looking at two different universes in those films. That New York, or more precisely, those New Yorks, were long gone by the time I moved to the city. The New York in Sleeping with Other People is very much of the moment, the suburban-chic Upper West Side and the trendy up-market Lower East Side singles scene; it hops around the city in a very familiar way-something that today's TV shows aren't really able to pull off. How did you go about setting the scenes throughout the city?  

I initially wrote the film to be set in San Francisco because I thought it would be fun if it was set in a different city. Little did I know that San Francisco is one of the most expensive places to shoot a film. The financiers of the film pretty much all agreed across the board that we shoot the film in New York. I've always been a bit of a reluctant New Yorker, if that makes sense. It was a very aspirational city for me, coming from Maryland. But then after going to NYU and living here on and off for the last 10 to 15 years, I've grown to have a complicated relationship with it. I love it whenever I look out to the city from my window and think to myself, this is what I've always wanted. But then, and this happened just the other day, I'll be walking in the city, step into a hole, trip and smash my face. So once we decided to shoot in New York, I worked with my team to have a nice mix of "Movie New York" and "Real New York." And that's really my experience living here, because there is this idyllic quality to the city, but there's also the realistic aspect of living here ("gritty" is the wrong word to describe it), and I think that captures the reality of the characters in their age group. In Broad City, it makes sense that they live in Queens; in Girls it makes sense that they live in Bushwick. In this film, the characters are a bit older, in their mid-to-late 30s, so it makes sense that they move between boroughs. They might work in Chelsea but then they might party on the Lower East Side. There was a lot of thought going into it, not only in what the locations say about the characters, but in how New York can influence and affect any given scene.  

I continue to find myself drawn to the characters in your films, especially from a sort of comedic antihero perspective-I love that they are all, in one way or another, so marginally likable. Sleeping with Other People is no exception; there's a raw, nearly transgressive honesty to your leads in the film that was also very present with the ensemble in Bachelorette.  

When I started writing, I thought of my characters as cartoons that could feel my feelings and have conversations with each other that I was having with myself. Each character would embody some sort of world view that I had at one point held, thought about, or entertained. So it was very surprising for me when I made Bachelorette, first as a play and then as a film a couple of years later, when people would go up to me and say, "They're so unlikable!" I couldn't help but take it personally. I didn't really feel that way, I just felt that I was challenging myself and asking these sort of tough questions-Why do you hate your body? Why do you feel that you can't have love in your life?-through characters who were extremely flawed but were asking themselves very serious questions.  

If anybody is really honest with themselves, then no one is really that likable. We all have those threads of narcissism, self-preservation, and self-interest. It's interesting for me to start with characters from that place and see where they go. Once you start to delve deeply into the psychology of any character, you're going to find a lot of things you don't like. What really surprised me is that both the play and the film turned out to be comedies. It really wasn't my intention to be funny when I started writing, and I was mortified when people started laughing at Bachelorette on stage. I didn't realize that the pain I was writing about is so easily interchangeable with humor. I think most of the time the reason people laugh at my characters is because they recognize something in themselves, either something they personally identify with or know someone like that. The closest thing I can compare my characters to is Peanuts cartoons; they're cartoons but they're going through so many existential feelings that it's funny because they really shouldn't be concerned about those things-you're a kid, go play with a ball. My characters are a lot like that. Regan, Kirsten Dunst's character in Bachelorette, shouldn't be so worried about getting married-she's beautiful, she's got a great job, a great life; anybody would kill for that. It doesn't really make sense for her to go through this existential crisis because of somebody else's happiness.  

In recent years we've seen a couple of male filmmakers follow up an indie comedy with a high-profile studio gig, but we rarely see women making that leap. Manohla Dargis had a very interesting three-part series on the subject in The New York Times this past December, and I'm also thinking of Kyle Buchanan's story, "How Sundance Exposes Hollywood's White-Guy Problem," for Vulture. Why do you think it's so rare to see women working in independent film get the chance to take on higher-profile films?  

That's a good question; I'm having trouble thinking of a woman who has actually been able to make that leap-especially with a studio comedy. Karyn Kusama did Girlfight in 2000 and went on to do Aeon Flux and Jennifer's Body years later. Kimberly Pierce made Boys Don't Cry and then directed the Carrie remake nearly 15 years later. You're looking at a good decade before these women are offered studio gigs, and the movies I just mentioned aren't even comedies. I really can't think of any women who fit the model of going from an indie comedy to a studio comedy; I'm not sure it even exists. The answer you might be looking for is that women have to go above and beyond to prove themselves and get these kind of opportunities, but the sad truth is that we don't even get the chance to go above and beyond to prove ourselves. You don't really even get a shot at that stuff a lot of the times. I've chosen to make my films independently because I want to make the films the way I want to, and the independent route makes the most sense for that. Is your question geared more towards the trend of seeing some people going from directing 500 Days of Summer to The Amazing Spider-Man and from Safety Not Guaranteed to Jurassic World?  

It's an observation a number of people covering the film industry are making-a lot of the promising women filmmakers whose work we get to see at film festivals don't end up helming a studio movie for a number of years, if at all.  

Definitely not in two to five years, no. Somebody once said to me that men get hired on their potential and women get hired on their experience, and I think that quote really nails it: it really does come down to plain old black-and-white sexism. 500 Days of Summer is a wonderful movie made on a budget, and Marc Webb did a great job directing it. I can see how a studio executive looked at that movie and gave him the Spider-Man gig; those movies are basically about the same sort of character-it's a connection they can make rather easily. I'm not sure too many studio executives can make that connection when they see Bachelorette, however, not if I went in and pitched a thriller. They'd probably just go, "But you just directed a wedding movie." Yes, but there's a lot of Steadicam shots in there, a lot of tension that I'm building up for the last 40 minutes, following multiple characters, and so on. Now, I haven't had the direct experience of going through that, but I'm assuming not many studio executives would be able to make that leap. It's just pure sexism, and it becomes a problem because we can't get the experience without being hired on our potential. We're in a no-win situation; many women would love to tackle these kinds of movies, but the reason we don't get to see it is because other people can't make that leap with us. I haven't had that much experience with these issues, though, because I write my own stuff and go out and get the money for the projects and that's really hard in itself. Even after the movie is made, it's really hard to just land a fair distribution deal; you're just fighting against the tide.  


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