How ‘The Shining’ and ‘Back to the Future’ Influenced Sundance’s Favorite Romantic Comedy Director

When considering the work of playwright, screenwriter, and director Leslye Headland, two thoughts come eagerly to mind: no bullshit, all passion. Fiercely intelligent with an incredible sensitivity and emotional understanding, Headland’s writing first struck me upon reading her bitingly honest and funny play Bachelorette, which later became her Kirsten Dunst led directorial debut in 2012. And after anxiously awaiting its followup, Headland’s new feature, Sleeping With Other People, premiered at Sundance last week.

Turning personal pain into universal comedy, Headland’s latest film puts a screwball comedy spin the classic genre to tell the story of a romance that blossoms between two self-sabotaging love addicts. Starring Alison Brie, Jason Sudeikis, and Adam Scott, Sleeping With Other People explores the old, “Can men and women really be friends?” debate, but is a far cry from its When Harry Met Sally parallels. 


Whether its her plays or her films, Headland’s work has an unwavering voice that’s just as enjoyable to listen to and as quick-witted as her films. And considering talking with her is like taking masterclass in cinematic appreciation and the intricacies that make us fall in love with movies in the first place, earlier this week I chatted Headland and asked her to tell me all about, both the films that influenced Sleeping With Other People, and those she continually has playing on repeat in her home.


THE APARTMENT, Billy Wilder 

The Apartment is the movie I will always be making. I was just saying to a friend of mine, who hasn’t seen the movies and we’ve been friends for years, that you have to see this movie or you won’t understand who I am. Everything about it, every single frame of it, is me. I saw it very late in life, when I was in my mid-20s, and after watching it immediately wrote a monologue about it and put it in a play. Ever since then I’ve been obsessed with it and watch it many times a year.

It’s unbelievable how much Billy Wilder thought about every single shot, how many takes he did, and how economical he was. I didn’t go to film school so I learned from watching commentaries on films like this and from the Criterion Collection and just reading about filmmakers. Wilder is someone whose work I watched when I was younger but I don’t think I really got it and got what he was doing until my mid-20s.

In Sleeping With Other People, the love triangle is inspired by that. There’s a young woman who deserves a lot better but is incredibly hung up on a man to the extent that it’s completely ruining her life. The story of The Apartment is about the guy who goes from being a schmuck to being a mensch. I think probably ever story I’ll ever tell is just people who are schmucks turning into mensches—they’re not perfect, but they’re relatively decent by the end of it.



The first shot of Sleeping With Other People, which is also in Bachelorette, I cribbed from The Shining. It’s were the camera is right underneath Jack Nicholson and he looks into the lens really quickly; he does that in The Shining when he’s locked in the pantry. That’s a shot that when I was a little college student watching it over and over again noticed and was like, oh my god, that’s the coolest fucking thing I’ve ever seen. Even in the documentary by Vivian Kubrick you can see him shooting that. So that’s how I can sneak in something that’s just for me in there.



I didn’t see When Harry Met Sally until I was 28. I’d seen Annie Hall when I was much younger. My parents showed me that movie when I was a kid, so i was sort of over Annie Hall by the time I got to college because my parents had been quoting it to me forever. They dressed me up as Diane Keaton for Halloween, which was basically just putting me in little boys’ clothes, and I would go out and people would think I was a hobo. So I was very much brought up on Woody Allen.

But When Harry Met Sally, I always thought that would be an Annie Hall knock off or something that I would’t be interested in. Then I actually watched it, probably around the time that I left being an assistant to become a full-time writer, and I wasn’t as taken with it as much as I would have been if I’d been younger. I think because I saw it later, I was really watching it much more from an analytic point of view, like, wow, everything is stolen from this. This basically cemented the genre in 1989 and we have not changed it since then. We’ve essentially just been watching the same movie, in this particular genre, for the last 25 years.

But I don’t believe men and women can be friends, so when I was writing Sleeping With Other People, I thought it would be interesting to put some breath into the same idea that the film did and explore why this whole genre is beaten to death and how can I reinvent certain elements of it. Ultimately I did a good job, and the actors did a good job, of slyly and very subtly twisting or playing with each beat that a romantic comedy has been hitting for the last 25 years, but depending on how you feel about romantic comedies will probably dictate how you feel about the movie. 

If I can be so bold, Quentin Tarantino for example, he is like, okay I’m going to do a western, I’m going to do a WWII movie, I’m going to do a grind house kung fu movie. He basically takes these genres that are dead and he does them in his own way and does them in the way he wants to, and that’s fucking awesome. In a lot of ways he doesn’t revive the genres, and I’m not comparing myself to Tarantino, but I decided to revive a genre that’s still going. It’s alive but sort of dead in its tracks. I don’t think it ever caught up to what’s going on.

Judd Apatow has set up a new mold where now the obstacle is: the schlubby guy or sexually inexperienced guy—like The 40 Year Old Virgin, which is a great movie—knows he doesn’t deserve this great girl and is going to try to get her or she’s going to get off her high horse and want him back…or something, I don’t know what’s going on there, but that’s the closest thing we’ve had to something different. It’s interesting too because that means the romantic comedy is skewing more male than it ever has, and it’s even skewing more male than the people in Hollywood even realize. When they think of a romantic comedy they probably don’t include I Love You, Man or Role Models and those bromances, but those are romantic comedies—that’s what they are, they just don’t fuck each other at the end. 

My point is, I’m trying to do something that’s actually still going, which can be against me but also, I feel nice going through the wall and getting bloody, you know? It’s harder to really fully embody a genre than it is to try and revive one that nobody fucking cares about anymore. It’s hard and really risky in a lot of ways to make a romantic comedy that Billy Wilder would have or in the way he would have and really fucking do it. Part of the reason the genre is dying is because everyone is so cynical about love. We’re all fucking each other within ten minutes of meeting each other, so it’s like we’re all wary of a genre that says, “Love happens guys!” That’s why I personally wrote the story; I was really depressed and wrote a movie that ended up being a this happy romantic comedy, and I think that’s because I wanted to be happy again and I made myself feel that way.



With The Graduate—although I get a little bored once Mrs. Robinson leaves—it is sort of a weird romantic comedy about a guy that has this problem. It’s pretty high concept to tell you the truth, because there are all these moral and existential ramifications in falling in love with a married woman and then falling in love with her daughter. But Mike Nichols is a genius and it’s shot through with a lot of aching feeling in it. We wanted to capture a little bit of that every once in a while. My movie isn’t as innovative of a film as that, especially not as visually innovative as that or Punch-Drunk Love, but it does borrow from them. 



The Adam Scott character was very carefully crafted and developed. We basically stole his look from Jack Nicholson in The King of Marvin Gardens. I wanted him to look sort of like a tough nerd, like so nerdy that he seemed fussy—but Jack Nicholson is never wimpy even though he’s playing a wimpy character in that film. So we tailored Adam’s look to that. 



Borrowing from Punch-Drunk Love, we used anamorphic lenses and lens flares, but we only used them for when bad things happen. In Punch-Drunk Love they’re very beautiful and ethereal and show loneliness. We didn’t use them often, but when we did it shows something dangerous. Punch-Drunk Love is such a great example of a movie that’s not really about what it’s about. It’s about love, but it’s actually about P.T. Anderson’s idea of what love is, which he tells us in the first five minutes of the movie.

Adam Sandler’s character has the conversation with the customer service guy, walks to the end of the driveway, stands there, and there’s that big, beautiful car accident and then the harmonium is dropped in front of him—that’s an analogy for everything. That all takes place in just a few minutes of screen time, but that’s what the movie is all about, and that’s what P.T. Anderson feels love is: a big, huge car accident that ends with an instrument you don’t know how to play, and the rest of the film is him learning how to play this instrument. That’s my interpretation. You meet someone and they change your world in this really almost violent way and then you have to learn the instrument of being in a relationship or being in love with them.

That probably took 35 viewings of that movie to realize, but you think and think and you watch and watch and then you say, okay, how am I going to do that? P.T. Anderson probably doesn’t sit there and think and think about it because it’s coming right out of his body. I feel that too once I’m there, it’s just coming out of my nerve-endings and just shooting out there.



My number 2 film ever is Back to the Future, and that’s just narratively. That’s the movie that I always endeavor to write when I sit down, but never do. Not genre-wise or subject matter-wise, but narratively that film is perfect, it’s just perfect. You’re never given a piece of information you do not need narratively and everything folds into the other. There are other films that do that too, like L.A. Confidential or Zodiac, but with Back to the Future I’m idolizing the least boring movie on earth. I’m making my version of that, whatever it’s going to be—whether it’s three girls doing cocaine or two love addicts falling in love with each other, I just want to make it Back to the Future good.

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