Leslye Headland Wants To Make Movies For People Who Are F*cked Up

By  · Published on September 10th, 2015

IFC Films

“These two jump off the screen,” Kate Erbland wrote after Sundance, referring to Jason Sudeikis and Alison Brie, “handily accomplishing the number-one feat of any rom-com ever made: getting the audience to blindly, fully, hopefully desire that they end up together. We’ll put it this way: Sleeping With Other People satisfies.” Genuinely rooting for a couple is a rarity with romantic comedies these days, but that’s exactly what writer-director Leslye Headland’s latest film accomplishes.

Sleeping With Other People embraces the tropes of the genre from the very beginning. Jake (Sudeikis) and Lainey (Brie) are two friends who agree not to sleep together, and, based on that description, you can probably guess what happens. Headland doesn’t try to subvert or deconstruct the romantic comedy, but instead presents a love story with honesty. Sometimes that honesty is funny and sexy, but sometimes, like when it comes to Lainey sleeping with a married man (Adam Scott), it can also be brutal.

The film lives up to its title too and delivers a very sexy movie along the way. Because of that, we spent much of our discussion with Headland discussing the highs and lows of sex in cinema in addition to the kinds of stories she’s interested in.

Here’s what she had to say:

It’s refreshing to see a movie with such frank discussions about sex. You don’t see that too often.

I know. It’s such a bummer. In comedies sex is just the thing you get to do with the hot chick at the end, you know? It’s just not at all talked about. I’m glad it’s a funny film, as well, because it could have been too depressing [Laughs].

[Laughs] Some of what Lainey goes through is pretty tough, though.

Oh gosh, yeah. That’s real life [Laughs]. It’s all just mined from my experience. Alison and Adam we shot in the first week, and everyone was like, “This is really depressing.” [Laughs] There was no Jason, so it was just a movie with Lainey and Matthew (Scott) ‐ and that movie is too much.

Sex isn’t a joke. In recent films, it’s, “Those guys had sex!” Sometimes there’s an emphasis on the realism of it, like in Blue Valentine and Blue is the Warmest Color. Those are great sex scenes, but we didn’t want to do that at all. I don’t find them to be titillating in the way these scenes needed to be. These scenes needed to be dangerous, weird, and, at the same time, you had to feel taken care of.

It’s like a magic trick. When you watch a magic trick, you know the dove doesn’t disappear. You know that, but you’re still very excited it disappeared [Laughs]. When you’re watching Adam Scott and Alison Brie, you know they’re not having sex, and yet your brain is telling you, “They’re fucking. Yeah, but… they are fucking each other.” [Laughs] To me, that’s more exciting, which is why I didn’t want to do any nudity in those scenes. Once you do nudity, there’s an element of realism that gets injected there. For me, I sort of think, Oh, the actress is showing her tits. You’re sort of taken out of it. My God, I’m just going on and on…


[Laughs] I’m not sure Steven Soderbergh has ever done a nude scene, but in the audio commentary for Out of Sight, he said it’s much sexier if the actor isn’t nude ‐ and that it does take you out of the movie.

I totally agree. I think in Solaris there’s a weird sex scene, but you don’t really see anything. There’s suggestive nudity. He’s a big influence of mine. I like hate-love him. Sex, Lies, and Videotape is one of the greatest movies of all time ‐ and it’s just talking. It’s literally just people talking about sex, hard-ons, and all that stuff. I don’t know… I don’t know. Sorry, my brain just got lost thinking of all these weird sex scenes [Laughs]. I was just going through all of them, thinking, Well, Rooney Mara does get naked in Side Effects, but it’s different! It’s just one moment, though. It’s over fast with her falling down, when she has an orgasm on “the meds.” Her sex drive is back, which is the point of the sex scene. It’s sort of aggressive. I guess it’s assaultive… I don’t know if you can tell what a film nerd I am. [Laughs] Let’s just talk about top Soderbergh sex scenes! No. 1 is obviously Out of Sight.

I actually wanted to ask you about that. Since this is a sexy movie, what movies do you consider sexy?

Oh shit, that’s a really good question. [Pauses] Sex, Lies, and Videotape is a really sexy movie. I like fucking as much as the next guy, but what that movie taught me about sex is just unbelievable. I think it’s a lot more exciting than consummation, honestly. So much of it is about power dynamic, loss, and mutual depression. I just thought, My brokenness matches your brokenness. Sorry, I’m going off-topic, but for women, especially as a female filmmaker, so much of female sexuality is represented by, “My brokenness is fixed by his unbrokenness!” Then you have Pretty Woman, which is the least sexy movie about a sex worker ever. The movie is great, but it’s not sexy. I don’t find her sexy in that movie. I think she’s wildly charming, but I don’t think, I wanna fuck Julia Roberts. [Laughs] How many people watch that movie and go, “I can’t wait to see her fuck”? Have you ever heard of man say they want to fuck Julia Roberts?

[Laughs] I’m not sure I have, but she is in Closer, which is another sexy movie. At times, I guess.

It is! So depressing, though. That’s the only bummer. I think the first hotel room scene in The Graduate is one of the sexiest scenes in the world. I think a very close scene after that ‐ and they’re both seduction scenes, not sex scenes ‐ is Cathy Moriarty and Robert De Niro in Raging Bull. Both of them are very similar, in that the men seem to be doing all the work, but they’re actually not. So much of the comedy comes from Dustin Hoffman talking, trying to hang up her coat, and him not knowing what to do, as she’s literally undressing [Laughs]. She’s just like, “It’s all good. We’re going to fuck each other.” It’s not until she’s like, “Are you a pussy?” that he fucks her. Actually, it’s when she asks if he’s a virgin, and then he’s all like, “No! I’m going to fuck you now!” That last shot is the beautiful face she has on of, like, “finally.” Then the door slams, the lights go out… a lot of practicals in that movie, too, in the sex scenes: the ventilator and her turning on and off the lights, which is so brilliant to cover a scene. We used practical in the sex scenes in our film as well: the light that comes on between them is practical. It’s all very, very subtle stuff, but I think it’s one of the reasons why you find the scene sexy. You’re not responding to it because it’s hardcore fucking, but the power dynamic.

I’m going on and on, but Mike Nichols is European-Jew and Scorsese is so Catholic, and… I mean, in that Raging Bull scene, there’s a fucking crucifix hanging over the bed! In the story, she’s 16, while in real life, Cathy Moriarty was 17 or 18. He’s Scorsese, so he totally could’ve gotten away with him just boning her, you know what I mean? I grew up very Catholic and religious, so I can’t say that I don’t have that experience of feeling bad almost immediately afterwards [Laughs].

[Laughs] I’m curious, just to throw a title out there, what do you think of Eyes Wide Shut?

I think it’s destroyed by the digital people they put in it. Not to be a big, super purist, but in order to get that R-rating… I think that was the last thing he had to say: the last frontier is sex and relationships. It’s funny, because John Cassavetes started there, like it was the only thing that mattered [Laughs]. Kubrick went everywhere, and then, at the end of his life, he went, “I guess it’s maybe love? Let’s talk about that.” It’s sort of his final statement. I feel like a lot of that movie would make more sense if right in the middle of it was a huge orgy scene, and you’re actually watching people fornicate, in that real feeling of the camera making you feel like you’re that guy.

I honestly think it’s ruined by the digital people. I had like a nervous breakdown at 18, thinking, How could they do that? Everyone was okay with it! How could they do that? Somebody dies and someone says, “He probably would’ve made this decision.” You don’t know that! They don’t know what decision he would’ve made. Even if he made that decision, if I may disagree with Kubrick, on your film site, I still would’ve disagreed. That’s my vibe on that. I love the film and love that it’s a fake New York. I think Nicole Kidman’s character is unbelievable. I think people are too hard on it, because it was his last film. Isn’t it so brilliant? It’s such a dream.

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It has one of the best endings, too. Bringing the conversation back to your film, how did you feel after the experience of telling a story as personal as Sleeping with Other People?

All of this is my experience. It’s me being vulnerable as a filmmaker, writing and directing a story that was very, very close to my heart. You know, something like Bachelorette, I don’t know any of those women. They were always meant to be like cartoons. It really scares me when people say, “Let me tell you about this story about a bachelorette party,” and it’s so much worse than the movie. That’s not what that was suppose to be about. I don’t have friends like that. I don’t really experience that pathology anymore, and when I do, it’s very removed, as opposed to things I feel head on.

Sleeping with Other People came out of a very, very, very real loneliness. Not that the characters are based on… well, Matthew is based on three people. There are three men I’ve had relationships with who could watch this movie and go, “Yikes! I didn’t realize I was that guy in the movie.” Jake is so many different people, including myself. I got really honest about my own loneliness ‐ my fear of never really being close to anybody or never falling in love. I wrote this story and directed it with an intense honesty. The actors got really honest and real with me, which helps you lead the way as a director, rather than being a removed asshole. You can come in and be like, “Hey guys, I’m going there, too. I know you have to do it in front of the camera, but I’m going there, too.” I was always crying on that set [Laughs]. To me, it was either so sad, so beautiful, or so funny. It was a constant vulnerability, and I think that’s why the film doesn’t feel too formulaic.

To be honest ‐ and I’ll be honest with you guys, since you’re real film nerds ‐ it didn’t really occur to me what a rom-com it was until I saw the assembly cut. Of course I knew it had a rom-com feel, but I didn’t realize until later it was a hardcore rom-com, not just us referencing some tropes. [Laughs] I was nervous, because I’m not a huge fan of rom-coms. I like the old ones, but they’ve been in trouble for a bit. I thought, I hope people don’t hate it just because it’s a rom-com. There is a lot of romance, vulnerability, and conversations we just don’t have ‐ like, where the clitoris is, to be in a relationship with a man who absolutely does not love you, or to be the 40-year-old guy who’s still fucking bitches. I have very good friends who will roll up with a 20-something, and I worry about them [Laughs].

This is all just a long-winded way of saying, yes, it’s personal and me being vulnerable with myself, talking about what I’ve experienced. It’s a horror show, but it’s out there.

You’ve called the film “When Harry Met Sally for assholes.” Lainey and Jake can be assholes, but it’s that vulnerability you speak of that probably makes you like them.

I totally agree. The other helpful thing is the world they live in is not necessarily a friendly one. Genre aside, so much of Sleeping with Other People was about creating that emotional vocabulary for people, for people who are dating. Like, here are a bunch of archetypes you can point to, like, “I wonder who my Jake is. Who’s the person I want to be emotionally vulnerable with? Maybe I don’t necessarily want to have sex with them.” I want that instead of, “Who is my Richard Gere?” We still reference that shit.

It is about creating empathy in the audience for these people ‐ and that can come from recognizing these characters or their own struggles in the real world. I think what’s hard is there’s some people who will go, “I don’t want to empathize with these people.” When we were offering this script to people we heard, “I hate these people.” [Laughs] It was the same thing with Bachelorette. It’s fine that they don’t like them. Some people don’t want to go there with those people ‐ a dark place they’ve never been to, because they’ve always been a good girl, never cheated, and everything they’ve done is great. It’s, like, “Good for you! You win an award. The rest of us are fucked, and we’d like to have some movies to watch.”

[Laughs] Like you said, Bachelorette wasn’t reflective of your life experience, so, after Sleeping with Other People, do you want to keep directing movies that do reflect your experience?

I don’t think so. I think I’m too chronically dissatisfied, to be honest. Usually when I write a story I create characters to feel my feelings, and that usually comes out of a place of anger and frustration ‐ and that’s where Bachelorette came from. I just thought, Fuck this, guys. We’re all trying to get married? What? That’s still happening? That’s still a thing? When both my sisters got married, I thought, Everyone here hates everyone. What wedding are people referencing?

I think my work will always come from that chronically dissatisfied place of, “Wait a minute. We’re not going to talk about that? We’re not going to talk about people fucking each other without knowing each other? No one is going to say anything?” I think what genre that ends up falling in is like a magical thing I can’t control. The next one could be really funny, but I’m writing a thriller right now about a married couple ‐ a newlywed couple that commits a murder together. It’s kind of like Hitchcock or Cronenberg, but it might end up being funny. I have no idea. At the end of the day, I might have a read through and think, Oh, it’s funny. Now that we know it’s funny, let’s start making these decisions and choices.

I’m the anti-Tarantino at this point. He’ll go, “I’m going to do a Western! I’m going to do a mystery! I’m going to do this!” I start with, “What am I pissed off about?”

Sleeping with Other People opens in limited release on September 11th.

Longtime FSR contributor Jack Giroux likes movies. He thinks they're swell.