Writer/Director Leslye Headland’s sophomore feature film, Sleeping With Other People, takes a look at familiar romantic comedy conventions through the a decidedly modern and realistic lens. It pairs Allison Brie (Mad Men, Community) and Jason Sudeikis (Saturday Night Live) as “friends with benefits” who treat sex as a sport, however in their case, the “benefits” don’t include sex with each other. Headland’s first film, Bachelorette, starring Kirsten Dunst, similarly flipped the common, “wild-last-night-of-freedom” motif on its ear, earning Headland notice for her fresh voice. She was kind enough to join us for an inside look into her latest film, now playing on DIRECTV CINEMA®.
Sleeping With Other People has been called an update on When Harry Met Sally, and you’ve also mentioned finding inspiration in The Apartment. We’d argue “SWOP” offers something unique in its more realistic and intimate take on modern male/female friendships and sex. What were you hoping to tackle that you felt maybe hadn’t been done before and were you concerned with trying avoid traditional rom-com tropes?
Definitely was not trying to avoid any tropes. I’m not interested in reinventing the wheel. I believe as a storyteller that tropes, familiar story beats, and character archetypes are your friends. I like incorporating them into my films and plays as often as possible. I’ve always been interested in characters as symbols or cartoons that have real feelings. Like little Pinocchio’s stuck in a fake world playing a fake person and they want to become a “real boy” or a “real girl”. This seems the best way to explore really nuanced and tough subjects like morality, self-hatred, addiction, and intimacy. The internal life of an audience member is wildly unknowable. I don’t want to come at them opaquely or coyly. In order to crack it open, I like to entertain a viewer with what they think they know and then slip the truth in.
What was your initial inspiration for the film?
I’m always interested in women. I’m always interested in gender roles in conventional filmmaking. I’m very into writing about sex and how performative being a woman or a man is. I had just done a “wedding film” in a very unconventional way, which was my first film, Bachelorette. So I thought I’d do a romantic comedy. Most romantic comedies are devoid of sex. And if they do have sex scenes, it’s a joke or a weird romance trophy. It seems a shame as the younger generation is so sexually charged that really the only way you get to know someone is by hooking up. So the challenge was, could I make a classic rom-com with complicated sex in it?
In addition to working in film, you’re also a playwright, and many of your film projects, including Bachelorette, were originally written as stage plays. How do you find writing and directing for the stage versus the screen?
I usually use the analogy that a play is like blowing up a large balloon and filmmaking is swimming an Olympic race. They’re so wildly different and you measure your progress so differently. But both hinge on knowing when and how much to breathe. I’ve always felt that when and what you should expend your energy on is the key to creating art. Quality and talent and skill will all shake out once the piece is finished. When you’re in the thick of it, you have a lot of options on what to focus on and what you can commit to whole-heartedly. You must be smart about expending and conserving your attention and energy.
You’ve hinted at upcoming TV projects. Can you tell us what you’re working on next?
I have a couple pilots in development, but I am very excited about directing two episodes of the second season of STARZ®’s show Blunt Talk starring my personal hero, Patrick Stewart.
You brought together quite a dream team for this project, even in smaller roles. Jason Sudeikis, Allison Brie, Adam Scott, Adam Brody, Amanda Peet, Natasha Lyonne, and Billy Eichner onscreen, and Will Ferrell and Adam McKay offscreen as producers. Please say you’ll be working with some amalgamation of this team again…?
Of course! If they will have me. My first film, Bachelorette, had such a wonderful cast as well. I’ve been very lucky in that I’ve consistently gotten the opportunity to work with people I am real fans of. I only hope its a trend!