Leslye Headland on Sleeping With Other People
People that are sleeping with other people are the subjects of Leslye Headland’s new film. And it’s a laugh riot.
Headland is no stranger to comedy, having penned the play Bachelorette, which had an off-Broadway run in 2024. Bachelorette is part of a cycle of plays Headland has written based on the seven deadly sins.
Headland parlayed the success of her play into a directorial career, with the film version of Bachelorette marking her debut as a writer/director. While most critics called Bachelorette a female The Hangover, you could just as well describe The Hangover as a male Bachelorette.
In Sleeping With Other People, opening this weekend, Headland explores the nature of platonic friendships blossoming into true romance. Jason Sudeikis stars with Alison Brie. A brief prologue establishes that as college students Brie and Sudeikis hooked up for a glorious one-night stand. Several years later the two meet, in of all places, at a sex addiction workshop. In the manner of great comedies like When Harry Met Sally, they become friends but you know it’s only a matter of time before Cupid’s arrow strikes.
At beginning of film Sudeikis seems to be doing some serious stunt work. He’s chasing an angry fleeing femme down a New York City street and he barely manages to dodge a cab intent on running him over. This scene announces that Headland not only has a keen ear for dialogue but a sharp eye for action oriented camera shots.
“That’s all Jason,” says Headland to Free Press Houston in a phone interview. “That was the first day of shooting too,” she adds laughing. “It’s all about tricks, picking an angle where he looks close to the car. Cutting on the hit, using a longer lens, the sound effects.”
The film also stars Adam Scott, Adam Brody, Natasha Lyonne, Amanda Peet and Katherine Waterston. “I’ve known Katherine since college, and she was in my play Bachelorette,” says Headland. “She played the part Lizzy Caplan ended up playing in the movie version.”
There are moments in SWOP that will have the audience laughing in unison, like a scene where Sudeikis shows Brie how he thinks women masturbate. Likewise there are movie moments scattered throughout that refer to other classic films.
One such scene has Sudeikis throwing a bouncing ball back and forth in his small office. “That was Jack Torrance in The Shining or Steve McQueen in The Great Escape. We put a lot of stuff like that in the movie,” says Headland.
“I enjoy working with actors who are comedians. They are more aware how a scene can go from being very funny, to being serious, to being funny again,” With dramatic actors, sometimes its hard to get them to play the comedy in a heartbreaking scene,” says Headland.
Previously Headland also helmed About Last Night, based on David Mamet’s play Sexual Perversity in Chicago. “When I was hired to write About Last Night I was hired to rewrite the movie more so than to adapt Mamet’s play,” says Headland. “There are still Mamet lines in the Kevin Hart film, it’s just that people don’t bother to find them.”
-Michael Bergeron
