‘SLEEPING WITH OTHER PEOPLE’ Q&A: Director Leslye Headland Dissects the Complexities of Modern Dating

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Cole Clay // Film Critic

SLEEPING WITH OTHER PEOPLE isn’t exactly trying to reinvent the romantic comedy– it’s attempting to bring some levity to a nearly dead genre. Director Leslye Headland first came to prominence when she directed the comedy BACHELORETTE, starring Kirsten Dunst and Rebel Wilson. Headland not only is incredibly intelligent coming from NYU’s prestigious Tisch School of the Arts, she does not deny pop-culture’s place in society– and we get into that during the below conversation.

Featuring some of comedy’s most talented stars and up-and-comers – including Jason Sudeikis, Alison Brie, Adam Scott, Jason Mantzoukas and plenty of others – Headland’s raunchy words are brought to life with heart, laughs and more R-rated material to satisfy your cravings. Simply put, SLEEPING WITH OTHER PEOPLE is just a really funny movie start to finish.

Fresh Fiction had the opportunity to chat with Headland about the film.

I wanted to first ask you a couple questions about New York. You went to Tisch. I know it had to be different from the typical college experience in terms of a vast amount of culture. I’m not sure, what did you study actually at Tisch, specifically?

Leslye Headland: “I studied drama, actually. For four years I went to playwright’s horizon theaters, which is actually … It’s in the drama program. I directed theater for four years.”

I just ended up locking myself in my bedroom my last two years of college, and watching just tons of things from Woody Allen, to documentary like GREY GARDENS for example. I come from a small town in Texas, so my lexicon of films during my younger years was the popular 90’s drab with Adam Sandler and Michael Bay, Nicolas Cage kind of stuff.Anyway, what I wanted to ask is, when you’re studying that … I know you’ve adapted David Mammet before. Whenever you were in those form of years, what stuff really opened your mind up to different schools of thought, or maybe influenced you in your writing?

Headland:  “I have sort of an opposite upbringing. A lot of it started there. My parents were oddly, very … It’s so funny, because they were showing me Woody Allen movies when I was seven or eight. It’s like they just wanted me to watch what they were watching, but then I wasn’t really plugged into pop culture, because I didn’t watch the movies that you just find. Those I found much later in life. I think I have this weird pedigree of really knowing my stuff, film wise, and being very well educated on the classics, and film history and all of that. But then I have this real, real love for trash. I have this real, real adult love for stuff that is just poppy and not at all distinguished… You know what I mean?”

Yeah I do, it’s difficult to get the balance right between pop and art, but the answer is right there, it’s called “pop CULTURE” for a reason and it has its’ place.

Headland: “I think that’s why my films, they’re very technically proficient. Both of them were shot in under a month. The performances are really great. They’re very different ones, if you will, but both of them genre-wise, are extremely flashy. I did Waiting for Godot as my senior thesis project when I was at Tisch. My professor who is my mentor, he had mentors on the project on the thesis, and when I came in  asked him what he thinks my style is? He was like, ‘that’s a very 22 year old question.’ … you know? He said, ‘I think you are incredibly smart and I think really stupid shit makes you laugh.’ And honestly I think that basically sums me up, now, ten years later just as much as it did at the time when I was trying to direct Beckett.”

Yeah, no joke like pop-music too, and on Spotify right before you called I was un-ironically listening to Beauty & The Beat and Call Me Maybe to get me pumped up for the morning. 

Stars of SLEEPING WITH OTHER PEOPLE Jason Sudeikis (left) and Alison Brie (Right)

Stars of SLEEPING WITH OTHER PEOPLE, Jason Sudeikis and Alison Brie.

[Both Laugh]

But we both brought up Woody Allen earlier and couldn’t really wrap my brain around what he was going for until my late 20s, I don’t know specifically when. But I liked a lot how his films felt like they were pushing back against that bourgeoisie lifestyle while celebrating it to a certain extent. Like Adam Scott’s character in your film, and once he was introduced I instantly was like I love that … that New York intellectual that kind of reminded me in some ways of the Yale character in MANHATTAN, who thinks because he is the smartest guy in the room he can do whatever he wants. I’m not going to spoil what happens to him but you and I know what happens at the end of that, and it’s really neat.

Headland:  “It’s funny because my financiers … and they were great … They always want to make fun of something … They were a little confused as to why the bad guy was such nerd. You know what I mean? I think there is something in comedy now where it was, isn’t the nerd the good guy? Instead of the handsome guy? Shouldn’t the character be played like James Marsden? No no no, it should be a nerd… he should be a nerdy a**hole.”

Adam just does so well at being smarmy but also you can look at him and even though he’s a doctor he just had this… I don’t know whoever was the costume designer was just put him in this really funny professorial look… I wish I could pull that off, but at the same time this guy is kind of a joke in some way?

Headland: “It’s funny because Adam and I really came up with that character together. We really talked for a long time about it and I sent him a lot of pictures and stuff … we really wanted to create a male Mrs. Robinson. Like a sort of iconic sh*t head, which is a big part of the character kind of like Patrick Bateman [Christian Bale] from AMERICAN PSYCHO, and Aaron Eckhart in IN THE COMPANY OF MEN. There’s a lot of touchstones that really blend into creating and then what’s happening is it exactly what you said, when I watch it with an audience now what’s hysterical and what I did not anticipate. Is that the first moment he comes on screen and you see him, everyone starts laughing.”

Then literally two minutes later when they are having that sex scene you can feel audience is completely uncomfortable. It’s so exhilarating and so much of has to do with the collaboration between the designers, the actors, me, what’s on the page, what we decide not to shoot, what we do shoot… that collaboration … that kind of stuff just isn’t possible without that type of collaboration.”

Totally! And for me after watching it, it was really hard when I was just formulating topics of discussion I wanted to speak with you about … not to make it so personal (about myself) but I related to both characters so well in so many ways. Like for Alison’s character I know that feeling, of being so crazy in love and just not caring if you get hurt, or not. The sex scene in the office, it’s not an ideal place of passion and in some ways, at least the way I viewed it I would never want to participate in something like that, it just seemed degrading. But to her it was what that moment offered for her gave the character a touch point for her to grow as a person. through that … and learning. The film offered a lot of moments like that.

Headland: “I was going to say that I totally agree with you and I think that she doesn’t even see it that way. It was one of the reasons it was shot with a lens flare. That light that comes through there is a fractal that turned on and turned off that was something when I was doing research on sex addiction and love addiction there is this thing called euphoric recalls. Where you think that it’s more romantic than it was. For example, when I’ve had it’s very personal for me too, the film. A lot of this things I’ve been through with you in sort of creating another for. Yeah you know the I look back on them and I’m like the sex was so good, he’s so handsome and everything. You know if you really looked at it he is a f**king loser … he is using you to get off. You know what I mean?”

Absolutely.

Headland:It’s so degrading and it’s all about your dad. It’s just so total the opposite of what you thought it was. I’m waking up to that reality, like you said, waking up to that reality and learning from is for characters journey as well as Jason’s sort of realization not only is he capable of emotional intelligence, but he actually craves it. He just doesn’t realize it. Know what I mean?”

Definitely. I really kind of like how your characters didn’t apologize for their sexuality how it’s just so vapid. You know, you have Tinder and I could get on there and find 50 people to either just put in one category or the other and I really like how Jason and Alison’s performances come to grips with embracing that and just kind of showing that it’s not all bad and there are healthy ways and unhealthy ways to go about dating unconventionally. So, I just wanted to compliment you on the way that both characters are written that way. I thoroughly enjoyed it and I have been looking forward to it since Sundance and the casting was well done, and it seemed like everything gelled naturally.

Headland: “Thank you, Cole! I really had such a great time chatting with you and thank you so much for your kind words about the film. It really means a lot to me. I really put my heart into this one. I really appreciate it.”

It shows well and I will be looking forward to see what you come up with next.

Headland: “Thank you.”

SLEEPING WITH OTHER PEOPLE opens this weekend.