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Sundance 2015 Interview: Jason Sudeikis & Leslye Headland on “Sleeping with Other People”

Writer/director Leslye Headland’s new romantic comedy “Sleeping with Other People” has been appropriately familiarized to Sundance audiences as “‘When Harry Met Sally’ for Assholes” by the director herself at the world premiere. It’s a New York love story in which Jason Sudeikis’ Jake and Alison Brie’s Lainey work to maintain the one healthy relationship in their lives: their friendship. The catch is that they both have a tendency to fall into destructive promiscuity, with Jake an outed womanizer, and Lainey a woman who can’t stop cheating on her boyfriends with her manipulative college fling Matthew (Adam Scott). “Sleeping with Other People” is an impurely hilarious “friends with no benefits” tale, emboldened with bubbly chemistry between Sudeikis and Brie.

A progressive genre film that treats these romantic comedy antiheroes with heart, Headland’s hilarious follow-up to 2012’s “Bachelorette” boasts festive turns from an energetic supporting cast that includes Jason Mantzoukas, Natasha Lyonne, Amanda Peet, Katherine Waterston and Andrea Savage. In its exciting refresh to a film genre that currently endures mostly on non-cable TV shows, “Sleeping with Other People” knows the form of the rom-com, but challenges its rules. Headland’s charming narrative eschews expected moralization for its procreant characters that audiences are meant to love, and expresses itself with open sexuality that comes without the context of cheap raunch.

The day after the film’s world premiere at the Sundance Film Festival, sat down with Headland and Sudeikis to talk openly about their different kind of romantic comedy. Sudeikis had a humble tone when speaking about his new placement into the genre, while Headland paralleled her film’s fervor to challenge the squeakier preconceptions of relationships as shown through funny love stories. They discussed Jason’s newfound potential as a romantic lead, the way in which they both toed the story’s risky new morality, how the film takes after Billy Wilder’s “The Apartment” and more.

Leslye, what was it that appealed to you about casting Jason as your romantic lead, especially as his character is a dicier version of the male love interest?

LESLYE HEADLAND: When I met Jason I just felt like, “Why has this guy not been the lead in a romantic comedy?” It just didn’t make any sense to me. Jason had done some of them, but not in the sense of “here’s the guy.” And this whole movie is based on whether you fall in love with this guy, because if the audience doesn’t fall in love with him, they’re not going to believe that the girl fell in love with him. And that’s sort of one of the big problems I think with where the genre is right now. To me, the people are just not that intriguing. They’re usually people that have no problems, or their problem is that they’re a schlubby guy and they like a pretty girl. So it really was just a vibe thing. I met [Jason] and I was just like, I don’t understand why this guy is not in “The Apartment,” which is one of my favorite films, and one that we referenced a lot when we were making this film, or “When Harry Met Sally.” I just feel like the genre shifted somehow with the male leads, and it wasn’t the Cary Grants and these very funny, very handsome, very charming guys, that you as like a little girl watching “The Philadelphia Story” or “Bringing Up Baby” were watching. You don’t sit there and watch these newer movies and think, “Oh my gosh, I’m so in love with this guy.” As much as I love “Knocked Up” and as much as I love his movies, I am not in love with Seth Rogen. I’m sorry, I love the guy, I think he’s very funny, I definitely see all of his movies, but there’s no part of me that wants to fuck that guy. As relatable as a Seth Rogen character is, I just thought that as a woman, as a female filmmaker, and somebody that really wanted to make a romantic comedy, I just felt very lucky. I felt like I had found something before anybody else did. Even though he was very successful, he wasn’t the big guy. I don’t understand why women aren’t in the audience swooning. Like, I’m going, “Here he is, here’s the dude!”

Jason, youve done sex comedies before, like “Hall Pass” and “A Good Old Fashioned Orgy” that have a similar openness as with “Sleeping with Other People.” But you havent really lead a romantic comedy. Is that something that just hadn’t happened yet?

JASON SUDEIKIS: I was lucky to have Tina [Fey] hire me on to play her love interest early on with “30 Rock,” and it was in its first season before it would have gotten a much bigger star to play the part as they continued to do as the show became successful and whatnot. But I always loved scenes where people fell in love, like in sketches. I wrote scenes that had that at “SNL.” Like I tried “An Affair to Remember,” when Annette Bening hosted. I wrote a scene where I see her at the top of the Empire State Building. I turn around and I kiss her, and when we pull apart I realize it’s not her, it’s not who I thought it would be. She was waiting for a different guy, and I say, “Well, should we give this a shot now?”

But I can’t really answer it. I don’t know what I’m doing, I’m only seeing it out through these eyes, and I would argue that the reason is probably that people wouldn’t find me attractive enough, or that that would be my baggage and hang-ups on it. But I don’t know—small teeth, no cheekbones? Not to highlight my insecurities, but I don’t know why, and I don’t know why Leslie did. I don’t see it.

Your character Jake is outed pretty early as a womanizer, but even in an introducing scene when confronting an angry girlfriend that hes cheated on, it seems like you’re controlling Jake’s cockiness. How did you go about tackling this hurtful character without losing the audiences grace?

JS: I remember Will Arnett saying something to me that I always thought was really smart, which was that it’s kind of up to the writer’s and director’s goal to write unlikable characters, but it’s then up to the actors, through something that I have no conceit of or understanding of, to make it likable. So I am not modulating, I’m just trying to be as sincere as he’s written, as transparent as that character is, and just deliver that with every single bit and actually believe it in the end. That was all there, I just had to say it, punctuation and all that.

Leslye, what was your perspective on these new rules about whats fair game in “Sleeping with Other People”? For example, you have Alison Bries character sleeping with an engaged man, which is usually a no-no for winning over rom-com audiences. How did you want to navigate that divisive territory?

LH: To be completely honest, I’ve slept with men in relationships. It happens, you know what I mean? I think that one of the things that I said over and over to my department heads is that the bad guy in this movie is shame. It’s not the handsome guy that is going to steal Katherine Heigl away from Seth Rogen, it’s shame. It’s that idea of, the more that you hide where the clitoris is, or who’s sleeping with an unavailable guy, and who’s telling a woman that like for her to expect him to be monogamous with her after three months of casual sex and no discussion, it’s basically stupid. To really take it all out and air it, I believe that it’s very hard to dislike somebody being genuine. To piggyback off what [Jason] said, you might not like it, you might not like the characters or what I’m saying, but it’s genuine. It’s raw. If you say it truthfully, and you do it truthfully, and you speak from maybe not a place of personal experience, but definitely from a place of “this happens” … “The Apartment” was a big movie that we talked about a lot. Just because Shirley MacLaine is sleeping with Fred MacMurray’s character doesn’t mean that she’s a bad person. It doesn’t mean that she doesn’t deserve Jack Lemmon, it doesn’t mean that she’s not the heroine of the movie.

JS: She doesn’t believe she deserves it.

LH: She doesn’t believe she deserves it, and that’s the problem. And that’s very much like Alison Brie’s character, and [“The Apartment”] was made in 1960. It’s 2015, guys! Pull it together. Women don’t sleep with men who are in relationships, and men don’t cheat on their wives? Like, relax, this has been going on for a while, not to mention that it’s been happening on cable TV constantly! I think we can do it in the romantic comedy every once in a while, like, at least every couple decades.

JS: Well, we tried!

Do you think popular media audiences are looking for these discussions and this open talk about sex, but are not getting it?

LH: I just think people don’t talk about it intellectually, or emotionally intellectually I should say.

JS: Or empathetically. Lord knows that before me having relationships that have dissolved, whether breaking up with someone, or breaking someone’s heart or having your heart broken, then you start living life. Then you start listening to music with a lot more understanding. Then you just hear it differently, you understand the complications that go into things. You don’t just read Us Weekly and think, “Oh boy, I thought they were going to last forever.” It’s like, I don’t know what’s going on there; it’s a beautiful house that could have termites! You don’t know what goes on. So I think that if it lends to those conversations — I feel like it has with people that came up to me last night, asking questions — if it gets the conversation out in dorm rooms and fueled not necessarily a therapist but general conversation, I think that’s helpful.

LH: I feel like shame is a little bit like bacteria. If you expose it to light, it dies.

JS: Yes, absolutely.

LH: And I think that’s what this film does, it’s just like, “It’s out here, guys.” You can recoil, or you can lap all of it up, but that has to do with you, man [laughs].  

Nick Allen

Nick Allen is the former Senior Editor at and a member of the Chicago Film Critics Association.

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