READ MORE: Leslye Headland on Why ‘Sleeping With Other People’ is a ‘F*cking Rom-Com’ and Not Your Typical Indie
Leslye Headland’s got vaginas on the brain. She’s worried that they’re being underserved, underappreciated and underestimated, both by the straight men that fumble with them and the film industry that marginalizes or outright denies female sexual agency. As such, her newest film, the savvy rom-com “Sleeping With Other People,” doesn’t shy away from the hoo-ha bugaboo. It takes an unusually candid approach to sexual matters, epitomized during a scene in which our leading man, Jake (a womanizing scoundrel played by Jason Sudeikis), simulates female masturbation using a glass bottle for the edification of his romantic opposite, the serially cheating sex addict Lainey (Alison Brie). It’s discomfiting, funny, a little touching and altogether unforgettable.
“Sleeping With Other People” plays as both a love letter to and a level-headed commentary on the rich tradition of rom-coms that have preceded it, executing the same pleasurable beats that audiences expect, but doing so with more wit and pragmatism than any like-minded films. Jake and Lainey do frustrating, self-destructive things, but in her infinite benevolence, the kind god Headland recognizes that doesn’t make them any less deserving of happiness or love. Indiewire had the opportunity to speak with Headland about the female anatomy, Hays Code-era comedies and striking a balance between optimism and cynicism.
Let’s get right into it and start with the bottle scene. I realized that I felt kind of uncomfortable while I was watching it, until it dawned on me that that might be what you’re going for, divorcing sexuality from its glamorization. Could you speak to the sexual politics at play in that scene in specific?
For one, that scene is a metaphor for what’s happening to the characters throughout the film. He is literally teaching her how to love herself, and then she kind of does the same for him. It’s what real romance is rooted in, not that one is the perfect soulmate for the other one, but that they both give each other something they already had. [Jake and Lainey] both have all this self-esteem inside of them, but they need someone to put in the effort to bring it out. That being said, the scene gets pretty graphic about what the vagina looks like. To me, it was important that it’s a straight guy talking about this, usually you don’t see that. In romantic comedies, when straight guys talk about sex, that makes them creepy.
It’s a strange contrast, because there’s so much crudity in male-dominated comedies, especially sex comedies, but when it comes to frank discussion, everyone clams up.
I agree, totally. I gave it a lot of thought, like, “Should she talk about it? Should he?” But I knew he should do it. We need to see a straight guy talking about sex, and about how to pleasure a woman. It’s something [Jake] has put a lot of thought into, obviously, and it’s something he enjoys doing. I also thought it was fun to have a non-sex-scene sex scene. “When Harry Met Sally…” did it most iconically, when Meg Ryan’s pretending to have an orgasm at the deli. But that’s a trope that dates back to Ernst Lubitsch with “Trouble In Paradise” and Frank Capra with “It Happened One Night,” “The Lady Eve” with Preston Sturges — there’s always a scene like that, where the characters essentially have sex, but they don’t, because of the Hays Code or the MPAA. So my idea was to do a non-sexual sex scene for a generation who’s already seen everything, who can just Google “sex” and find whatever they want. How can you make it feel hot, and different? [pause] You know, I think it’s sort of funny that you felt uncomfortable during the scene! I wanna know why!
I dunno, I was watching it and knew it was something I wouldn’t feel comfortable talking about. As a fellow straight guy, it’s not something I would try to speak authoritatively on.
I think it’s also gotta be at least a little bit about the vagina. In the sex scene between [Alison Brie] and [Adam Scott], behind them in his office is a big poster of a vagina, it’s a diagram. I have it in my house because I inherited it from the production. My guy friends, my friend Michael came in, he saw it and I’m waiting for him to react, and he says, “Well, that just looks like something I’m going to fail at.” That’s also part of the whole scene, like, you’re not going to fail at it! It’s a body part. It’s fine! You can get in there and get excited and it’s not gonna hurt you. It seems complicated, but it’s not.
One of the most radical things that the movie suggests is that sex isn’t perfect. It’s not like the lights go down and everything’s blue and music starts playing. You deal with the fact that sex can be funny and uncomfortable and awkward and altogether more realistic. Is “Sleeping With Other People” intended as a rebuttal to the romantic comedies of the past few decades?
Absolutely. The number-one thing during shooting, the story, the pitch — it was not so much “can men and women be friends?’ as much as it is “what is sex?” People have sex often. For certain generations, it’s a question of freedom and creativity and genital liberation. For other generations, it’s been about power or domination. For others still, it’s about domesticating another sex. I wanted to know what it is now, and why is it being portrayed as dangerous or amazing? It’s about de-mythologizing sex. Sex is really weird. Unless you’re having it with your long-term partner, then it becomes something else, and that’s what I want my next movie to be about. But when you’re dating, what is sex about? If you’re having an affair, what is sex about? I think one of the reasons we like sex is because it’s a little weird… I like to say that sex is like time travel. You’re with a person, going through all sorts of different things with them, and you’re swapping histories without even knowing. It’s great, and it’s not a thing that needs to be cured.
Have you had the chance to see “Trainwreck” as of yet?
No, I haven’t, but I love Amy’s show! I’ve seen every episode, and I really enjoy, but I haven’t seen the movie yet.
Welp, it kinda speaks to these exact themes we’re discussing now. Shifting gears: You mentioned Ernst Lubitsch and Preston Sturges before, what is it that made you fall in love with their films in the first place? How did you first get introduced to their work?
I got introduced to Lubitsch through watching Billy Wilder. I had seen a couple of his movies because my parents are big movie buffs — “The Shop Around The Corner” and “Ninotchka” — but I hadn’t really gotten into him until I learned that Billy Wilder had been his protege. The coexistence of cynicism and optimism really attracted me. Just because you’re making an optimistic movie, that doesn’t mean that you can’t imbue some very deep pathos or tragedy within the story. “Shop Around The Corner” is probably one of the greatest quote-unquote romantic comedies ever made, and there is some dark fuckin’ sad shit in that movie!
When the guy fires Jimmy Stewart, that’s heartwrenching! There’s this incredible shot — it’s so Lubitsch, he does it all with one shot — where Margaret Sullavan is waiting for the letter and inside the mailbox, you see her hand go in. Not to mention how vaginal that shot is! He’s definitely making this film through an optimistic vantage point, but there are also sharp jabs of cynicism throughout. Wilder does the same thing — “The Apartment” was a huge influence on this film. There are huge washes of very broad comedy, the kind of thing that could be so sticky now, but it still works somehow. Even in Wilder’s noirs, “Double Indemnity,” which are so deeply cynical, they still have bits of optimism in them. It’s so funny that people think of me as, like, a “mean writer” or a “mean filmmaker.” I think my films are very optimistic!
Is there are a narrative of you as a “mean writer”?
I think because “Bachelorette” wasn’t “Bridesmaids,” people reacted like, “These girls are so mean! This is so mean!” And yeah, they are mean, because they’re very sad. It’s armor, they’re just sad people dressed up as mean people. And sometimes sad people behave selfishly.
That’s what human beings do.
And again, that goes back to Wilder too, the interest in human nature. Things like aspiration towards something else. Kubrick said that a satirist is someone who’s cynical enough to know what’s wrong with human nature but optimistic enough to make a joke about it. That’s how I feel, too. I go through my life depressed at the state of things, but I also think it’s sort of funny. If you point out how ridiculous our complaints or our sadnesses or our loneliness is, while also making room to pay it respect — those are the kinds of stories I’d love to continue making, if they let me, which they probably won’t.
As I understand, you were disappointed with “Bachelorette’s” reception upon its initial release. But I’ve been asking around, and at least in the circles I run in, it sounds like “Bachelorette” might be amassing a sort of cult following due to its second life on Netflix. Do you believe that your style of comedy, which is acerbic with an undercurrent of optimism, might not play well in theaters and takes more time to be appreciated? Or is it not that simple?
My gripe with how it came out wasn’t about any of that, honestly. It was very well-received by the people who understood it. I get people not liking it. It’s very aggressive. It comes right out of the gate and says, “You’re either going to care about what’s happening onscreen or you’re not, and now let’s go for ninety minutes.” Some people just don’t care, and that’s fine. The thing that’s more distressing is the state of the film industry. Not that creatively I wasn’t enriched, because I did, both by the people I made the film with and the people who reached out and told me they enjoyed it.
But we’re in a really shitty place in Hollywood and with filmmaking. I’m talking about the disappearance of the mid-budget movie, how everything’s either under one million dollars or over one hundred million. And the fact that quote-unquote “indie” has become a commodity, a recognizable thing. Audiences know what an indie film is, they can look at it and point one out. My film doesn’t look like an indie film. I grew up in the ’90s, when the whole idea promoted by Tarantino and the Coen Brothers was that you could make a mid-budget movie that looked big and lush and gorgeous, and then you could make that money back. And that’s what “Bachelorette” did.
But the general public discussion about the film was whether or not the movie was a success on VOD. The fact that I had made a movie in 22 days with movie stars that looks that way and behaves that way, and then it wasn’t advertised as an indie because that would’ve been a strike against it — that’s what made me depressed. I might be making movies that just don’t get into the world. I don’t know if I’m going to be able to keep making the movies I want to and survive in this landscape, financially and commercially. Specifically, how independent films are made now and perceived by the public. I mean hey, you’re here with a place called Indiewire. That never existed in 1994. “Clerks,” “Swingers,” “Pulp Fiction,” “Strictly Ballroom,” these were all things that you got to go out and discover for yourself, and they weren’t part of a brand. By the way, I love Indiewire, don’t get me wrong. What I’m saying is that if you make an independent film today, you’re expected to make it look and feel a certain way, which is against what independent filmmaking is all about.
The word “indie” describes genre as opposed to means of production.