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Sundance Women Directors: Meet Leslye Headland – ‘Sleeping with Other People’

Sundance Women Directors: Meet Leslye Headland - 'Sleeping with Other People'

Leslye Headland started her writing career in theater, with such plays as Bachelorette (Second Stage), Assistance (Playwrights Horizons), and the rest of the “Seven Deadly Plays” series (IAMA Theatre Company). Several of these plays would later serve as the basis for her film and television projects. In 2012, Headland made her feature directorial and screenwriting debut with Bachelorette, starring Kirsten Dunst, Rebel Wilson, Isla Fisher, and Lizzy Caplan. The film had its world premiere at the 2012 Sundance Film Festival and went on to become one of the most successful VOD releases to date. Headland’s next script, About Last Night, was released in February 2014 and grossed over $50 million domestically. (Press materials) 

Sleeping with Other People will premiere at the 2015 Sundance Film Festival on January 24.

W&H: Please give us your description of the film playing.

LH: Jake (Jason Sudeikis), a charming womanizer, and Lainey (Alison Brie), a remorseful serial cheater, help each other change their destructive dating patterns, developing a unique intimate friendship.

W&H: What drew you to this story?

LH: I challenged myself to write/direct a romantic comedy. People trash talk the rom com, but it’s one of the oldest cinematic genres, with stellar origins like Twentieth Century and Trouble in Paradise. I think as audiences lost their innocence, the genre lost its suspense. To create suspense, you need obstacles, so I gave my couple an obstacle that very few people ever overcome: their own behavior and their past.

W&H: What was the biggest challenge in making the film?

LH: My own vulnerability. Watching my own past heartache and experience day after day — it was gut-wrenching, cathartic, beautiful, and painful. That and shooting the film in less than a month.

W&H: What do you want people to think about when they are leaving the theatre?

LH: When it comes to dating, you’re not as crazy as you think you are.

W&H: What advice do you have for other female directors?

LH: Take yourself seriously.

W&H: What’s the biggest misconception about you and your work?

LH: That I only write about shitty people. Or that I’m trying to be shocking. I just think people are super weird, so I like to write characters that get addicted to things, lose their minds, hurt others, put themselves in bad situations. I’m just more interested in that.

W&H: How did you get your film funded? Share some insights into how you got the film made. 

LH: Jessica Elbaum at Gloria Sanchez secured financing for the script from Sidney Kimmel Entertainment, who provided funding for the film. I worked with Jessica on Bachelorette as well. She’s a passionate advocate for female writers and directors.

W&H: Name your favorite woman-directed film and why.

LH: I don’t believe in “favorites,” So I’ll choose four. The Heartbreak Kid (dir. Elaine May), Point Break (dir. Kathryn Bigelow), Real Genius (dir. Martha Coolidge), and American Psycho (dir. Mary Harron). All four films are so clever in extraordinarily different ways.

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