Sleeping With Other People Director Leslye Headland

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Film festivals always have their share of downers. One year at Toronto, I watched back-to-back movies on Rwandan genocide and sex-trafficking in New York before finding release for my built-up angst in the form of Juno. This year at Sundance was something of the same. The day after seeing the David Foster Wallace biopic and Kurt Cobain documentary, I was in a heavy place. Then came Sleeping With Other People, the hilarious second film from director Leslye Headland. Starring Alison Brie and Jason Sudekis, the romantic comedy is an homage to films like When Harry Met Sally. I spoke with Headland about making a film that manages to push the boundaries of sexual comedy without a single nude scene.

Paste: It’s always refreshing being at Sundance and seeing heavy movie after heavy movie and then coming across something so funny. So thank you for that.
Leslye Headland: You’re so welcome. Making people laugh is something I never intended to do. I wanted to be very heavy and very dramatic when I first started as a writer when I was in my twenties. And now I’m addicted to it. This morning [at the screening] through the walls, I was hearing people laughing, and there’s nothing better.

Paste: I’ve heard you say that you really thought yourself more serious and were surprised and even a little upset at people laughing during your plays.
Headland: Yeah, I’m just a big film nerd—like a really, really big film nerd. I grew up wanting to be like Woody Allen, Martin Scorsese, Stanley Cooper, David Lean, Frank Capra, Billy Wilder—there’s a little bit of comedy in there, but it’s like I just saw myself as this serious artist. And so going from plays into films, it’s just so funny. I meant to make these very important pieces of work, and then everyone was just losing their mind laughing about the whole blow-job monologue or the bottle scene. I guess there is just something important behind making people laugh about the things that are really, truly painful. There’s something about that that is serious in a weird way. “It’s a serious business,” I think someone once said about comedy. But I have come to embrace that aspect a little bit more.

Paste: Just seeing you up on stage talking about the film, it just seems like you have a knack for comedy even in the moment. Growing up, were you the one always cracking jokes?
Headland: Oh, I was always a ham. What you just saw up there was little bit of baby Leslye, you know? I had my moments. I wouldn’t say I was necessarily a class clown as much as I was a class provocateur. I was always like saying the things I shouldn’t say, talking to adults like an adult, and they were like, “Get the hell out of here.” I was definitely drawn to performing, for sure, and I loved attention as most people do. But I never thought about pursuing it as a career or anything like that—you know like being an actor, being a funny person. I think it was more, once you get those laughs, “Oh, I guess people like me. I guess I must be coming across in some way.”

Paste: If you were provocateur as a kid, that still seems to be true in your work. This film, it’s really pushing a lot of boundaries—it’s not your typical rom-com.
Headland: Yes! And that was the goal—to write a really legitimate romantic comedy that is heartwarming and fun, and you know has a happy ending, and that is almost sweeping in its scope, and then at the same time, really put into it some extremely painful stuff and touch on the things that are really hard about having relationships right now, in this dating climate.

Paste: Yeah, it’s funny that it references When Harry Met Sally so much, and that there was this period of rom-coms—many that had Meg Ryan in them—that was like a good age for the rom-com…
Headland: Yeah, yeah I totally agree.

Paste: But even just watching those movies today, they feel almost quaint. Things have changed so much.
Headland: So much, yeah. There was an innocence that was lost. I mean, it also happened between like the great screwball comedies of the ’30s and ’40s, and then when the sexual revolution happened. You really don’t see a revitalization of it until like, The Graduate and Annie Hall, which are still very dark. They are very much in this still very cynical sort of place—the famous ending of The Graduate was weird and ambiguous. And the ’80s sort of revitalized that—like you said—quaint sort of boy-meets-girl, shop-around-the-corner feelings. And now it’s like if you don’t talk about sex and those dating frustrations, they won’t seem like they are actually about love. Because it’s not about what people are really experiencing—real men, real women. You know most rom-coms start out with people with no problems, except they don’t have a person. Like that’s the only problem in rom-coms these days, and you know people have a lot of problems, and part of love is loving people despite those. And loving yourself in spite of those. Jason Sudeikis beautifully put it: “The movie is about two people who teach each other to love themselves, so they can actually embark on a relationship with each other.”

Paste: Yeah, it was interesting finding myself towards the end of the movie, feeling like of course they’re gonna have to end up together. But there was a point where she’s leaving, and I wanted them to be together, but I was also kind of happy for both of them because they were just in a better place. It wasn’t all about their connection; it was about their growth.
Headland: Yeah, it was about their growth as people and as characters, and I think in a weird way that scene is a little bit of the emotional life you have to have when you fall in love with someone, which is like, ‘What happens if I lose this person? Am I still okay?’ And I think the characters had to get to the place where they had to be, ‘I’m gonna be okay without this person’ so they could be together, if that makes sense. Most rom-coms rev up to “I can’t live without this person, and if I don’t have this person, I’m incomplete.” The moral of this story is that these people are complete without each other, but it’s just nice that they are together. They’re complete humans.

Paste: But it does push the boundaries—it seems like Cards Against Humanity has changed everything. We can all accept that, ‘Oh, we all find this funny.’ It’s sort mainstreams the frank sexual humor. But then there’s no nudity in this movie at all. Can you explain a little bit about that decision?
Headland: Oh yeah, it was a very specific decision because I am that provocateur that I was when I was a little kid. It’s less about the Buñuel—“let me slice somebody’s eye open and see how everybody reacts” or like Lars von Trier. I’m much more interested in “What am I not allowed to say? What is the thing that we aren’t talking about in a mainstream space? And why not? And if I put it in a package that’s beautiful and feels like a multi-million dollar movie—and it’s really an indie—and I have these really attractive people talking about it, and there are all these signposts saying it is a romantic comedy, and it’s got this great happy ending, but right peppered throughout it is this feeling of angst and frustration and a real frank discussion about genitalia, about the rules of dating, about morality, about fear, about pain, what is going to really set people off?” So it’s been very interesting to have the reaction—it wasn’t that I was trying to shock people necessarily, or anything like that. It was just more like, “Why can’t I talk about this? Why am I not allowed to describe the female genitalia in great detail?” It’s very easy to figure out where the clitoris is—it’s right here. And I’m going to make a scene where someone just points to it, and [says that]. You can feel everyone go, ‘We’re not supposed to know that.’ Everyone just goes, “No,” and I’m like, “Why not? It’s just right there.” All I hear about is dick and balls all day—I see them in movies constantly, you know what I mean? It just seems odd that I can’t say this other thing. And Bachelorette was very similar, but I think that this is more of a mature film, honestly, then that film was. Not to bad mouth it, but I think I’m just a more mature person, and had a clearer sense of what I wanted to say and how I wanted to say it and how I wanted to be provocative—as opposed to Bachelorette, I was more like, “Watch out assholes because I’ve been sitting here for like 10 years ready to make a movie.”

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