A Talk on the Wilde Side: Olivia Wilde’s Booksmart, Her New Home Behind the Camera, and Her Plans to Save the World

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Tim Rhys, MovieMaker Magazine (MM): You just had the premiere of Booksmart at SXSW, and by all accounts the reception was over the top amazing.

Olivia Wilde (OW): People really like it. And there are no guarantees, of course. So I’m really happy. But even more than happy I’m kind of amazed that we were able to cut through and people are picking up on themes that I wasn’t even sure anyone would get.

MM: Like what?

OW: For me, the movie is all about judgment and looking deeper.

MM: You’ve also said it’s about really seeing people for who they are, as well as yourself. 

OW: Yes, because if we keep putting other people into categories—and we do that in adolescence in order to handle the Lord of the Flies nature of high school society—we certainly do it to ourselves. And as we get older, maturity leads us to a place where we realize that we’ve missed out on something by making those judgments. We’ve kept a distance, and it’s a bummer that we’ve kept people at bay because we’re afraid of them. I’ve always thought that if we realized all this earlier, we could gain so much time. 

MM: It seems you’re always up for a challenge. It fascinates me that you chose a comedy as your first directorial effort. As you know, comedies can be fun to make but they don’t always “travel well.” 

OW: Right. So you have to make it more and more specific, and the more you do that the more interesting it gets to people. But you still have no guarantees that everyone will like it. That’s why it’s so scary. With comedy it’s so entirely subjective that you have no idea if people will laugh. It’s hard and yet it’s amazing because it taught me a lesson for the rest of my career, that if you take the time to personalize the material, it’ll all be worth it. And I don’t think I fully realized that until we showed the movie at SXSW.

Taking the bench: To coach Feldstein (R) and Dever (C) in between some of Booksmart‘s most challenging takes, Wilde (L) leaned on the good judgement she honed throughout her years in front of the camera. Image courtesy of Annapurna Pictures. Photograph by Francois Duhamel

MM: You just turned 35 while you were at SXSW. It’s kind of a monumental age. Society believes that you have now, in all ways, reached maturity. You can run for president, if you want to. Do you feel in some ways that you’re just coming into your own as an artist? 

OW: This was the best birthday of my life. On the night I turned 35, I premiered my directorial debut in front of 1,100 movie lovers, and then danced all night at a Santigold concert. So 35 is pretty fucking awesome. And yes, I do feel I’ve found my footing. I made the choice to do so, because I felt worthy of it. It’s amazing when we realize that our happiness and fulfillment is within our control. As you get older you just learn how to get out of your own way.

MM: So, are you as together as you seem? 

OW: Do I seem very together? That’s comforting. I’m learning to thrive within the uncertainty of the nomadic lifestyle and I’m constantly struggling to find the balance between my two loves: my family and my work.

MM: It’s always a sacrifice, isn’t it? As the director you’re talking about years of planning, pre-production, production, post-production, marketing. It’s an enormous undertaking and you’d better make sure it’s a story that will keep you interested and motivated. It took you a while to settle on the right project, but you finally found that in Booksmart. 

OW: I really did. And I’m here for press right now but then we still have so much to do in terms of creating the marketing concept. I think I’m trying not to abandon this baby because I care about it so much. I’m really hands-on with all this stuff. I can’t seem not to be. 

MM: Thus your director personality. You like to control the process.

OW: It’s interesting, because I don’t feel like I’m someone who demands to have to control over things, but I do like to participate in them. I think the director has such deep knowledge of what the movie is that, in terms of marketing, once you lose that voice the marketing can float off into this other direction. It’s not that the director has to control everything, but…

MM: But you have to influence it.

OW: Exactly.

Yachtshot: Wilde (L) sets up a shot with Booksmart star Skyler Gisondo (R), whose rich kid character Jared throws a yacht party to impress his classmates.

MM: And you’ve got your Booksmart necklace on, I see. 

OW: I do. I’ve been wearing it since the shoot. I haven’t taken it off since we wrapped.

MM: Why would you? Things have been going pretty well, it seems. 

OW: It’s my good luck charm! But yes, this film felt “worth it,” so to speak. Any first-time director taking something like this on, it’s really scary, a lot of work, a major commitment. But the reason this one felt like the right one was because it reminded me of the movies that made me want to make movies. And if I were to think about the way I discovered movies, I would have to go back to films like The Breakfast Club, Dazed and Confused, Clueless. They came into my life at different times but they all helped me contextualize the experience of adolescence. And I think that those movies can, if they resonate, help a generation to connect. I liked the idea of creating one of those generational anthems. And the other element was that it was a chance for me to be very personal in sharing my perspective on judgment, on adolescence, on acceptance, on confidence. I saw the potential for it in the original script. The script went through an enormous evolution, which I found to be such a fascinating process.

MM: You’ve produced other people’s movies for some time now. I have to ask you about one of them: Reed Morano’s Meadowland. At the risk of sounding hyperbolic, your performance in that film was one of the finest I’ve ever seen.

OW: Oh, thank you so much.

MM: But also, that material was just so brutal. How did you even… were you a parent at that point?

OW: I was. My son was very little, though. It’s interesting because as my kids have grown up, that movie and that role have become more and more heartbreaking to me and it’s kind of amazing that we were able to do it when Reed and I were both mothers. I think, “How did we even do that?” But we felt like it was an important exercise in confronting our own fears.

MM: I guess I’m a coward then. As a parent, I don’t think I’d ever go near that subject matter. 

OW: Well, I’m not sure if you know Reed, but she’s extraordinary. And fearless. She wants to tell stories that no one else will go near. I wanted to facilitate her directorial debut, so I produced and starred in that film and we developed it together. She rewrote the script from a very different draft and made it so personal. But in order to make it that personal she had to cast her own son as my son who goes missing, which was really brave. It’s interesting, and I’ve been thinking a lot about this recently… personalization is necessary to create the kind of specificity that yields good results in art.

MM: That’s good, did you memorize that? 

OW: [Laughs] No, I’ve just been thinking about what will cut through the dull end of the social fabric, and it’s always the most specific voices and stories. That’s the challenge for a lot of people, because you’re aiming to create something many people can enjoy, but in order to do that you must personalize it and make it a singular piece of art where it would be OK if only you enjoyed it. 

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