‘Sleeping With Other People’ Director on ‘Easy’ Male Leads, Sex Scenes With ‘Goody-Goody’ Alison Brie

Leslye Headland tells TheWrap about working with Jason Sudeikis and why she still considers ex-boss Harvey Weinstein her “movie dad”

Last Updated: September 11, 2015 @ 11:14 AM

Director Leslye Headland became a hard-edged indie queen in 2012 thanks to the VOD smash “Bachelorette,” a bawdy comedy about four female friends behaving badly.

Now she’s back on Friday with an equally raunchy take on the romantic comedy, “Sleeping With Other People,” starring Jason Sudeikis and Alison Brie as sex addicts attempting a platonic friendship despite an obvious chemistry between them.

TheWrap caught up with Headland to talk about her track record (“Bachelorette” broke records as an experimental day-and-date release in theaters and VOD), the perks of having a male lead, and all the changes at her former employer, The Weinstein Company.

“Bachelorette” was a big moment for you — how are things different with “Sleeping With Other People”?
It’s nice to have a male lead, co-lead, so it doesn’t immediately become, “Let’s talk about women!” It’s actually more about the process of filmmaking or love or the genre. So much work goes into a movie, at least for me. So much of my personal life, even if it’s not autobiographical.

So you would say it’s easier to have a male as a co-lead?
It’s definitely different. That’s one of the reasons I wrote the film. Coming off of “Bachelorette” press, I wanted to challenge myself and write a male lead. Also, I really wanted to work with Jason. He felt like a good match for me.

sleeping with other peopleJason Sudeikis and Alison Brie don’t seem like people with destructive tendencies. Did you have to recalibrate them to get these performances?
I was definitely excited to do a sex scene with Alison. [Her characters] are usually sort of pure, for lack of a better word. And Alison herself, I assumed maybe she was a little bit of a goody-goody? I didn’t know at her at all. When we met, we were so similar in our emotional lives. We were both very passionate and messy, we’re both very happy and with people that we love. So we were both able to explore that character. She got into it in a way that I wasn’t expecting her to.

And Jason — he was just so flattered by the part, because I wrote it the way I saw Jason. Not the cheating part, that was more premise stuff, but the way I see him as being somebody that could talk anybody into anything. He’s like, “Here, walk off this bridge.” He’s such a charismatic guy.’

Early on, you described the movie as “‘When Harry Met Sally’ for Assholes.” That’s been repeated in almost every story about you right now.
That really came back to haunt me, didn’t it? That’s something I said in the room, by the way, just to get money to make the movie.

Assholes are having their moment, though, with TV shows like “You’re The Worst” and “Difficult People.”
For me, maybe it’s about backlash. Especially for women, it’s like, “I’m going to sit through five years of guys behaving this way? No, I’m gonna fucking write a movie about that.” And really, the idea behind “Bachelorette” the play was like, “It’s ‘Hurlyburly’ with women.”

A lot of writers who started out the same time as me, all you get is blurbs from the studios that your characters need to be more likable. That’s a word that’s always there. But I sat through six seasons of “Breaking Bad” — I know that’s not true. And you have people like Lena Dunham and Louis C.K. doing it on TV.

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Going back to “Bachelorette,” that film was considered the bellwether for day-and-date VOD/theatrical release, and a maiden voyage for Radius-TWC. What do you think about Tom Quinn and Jason Janego departing the company for a theatrical venture?
I’m not surprised. I think that VOD is still like the smelly kid in high school with all the cool toys. That kid that has the new PlayStation and you’re like, “I don’t want to be his friend but I want to check out the new Mario Brothers game.”

Everyone acknowledges how important VOD is. It can make careers, like it did for me. But “Bachelorette” put Radius in the position to make movies like that more and more. But it does have this feeling, especially to talent: A lot goes into promoting a movie, and it’s like, “Wait a minute, why am I doing this if everyone is watching at home? If this isn’t an event?”

I’m not sure what would solve that. If anyone could do it, Tom and Jason could. But I also get wanting to go out into theatrical. That’s what I did with this film. Certainly, we got offers from other distributors about VOD releases, but for me it was important to at least try a theatrical platform.

As long as we’re on TWC, you’ve heard the studio’s president, David Glasser, resigned and then came back in the span of a few weeks. You must know something about the gravitational pull of Harvey Weinstein.
Fuck, yeah! Dad? It’s hard to leave Dad. I don’t know David, though.

You know, not to steal the Olive Garden’s thunder but when you’re there, you’re family. I don’t think that I’m ever not going to feel like I’m part of Harvey’s world. Even though we didn’t wind up doing this movie together, he’ll always be my movie dad.

“Sleeping With Other People” opens in select theaters Friday.