Olivia Wilde Won't "Pick a Lane"

Hollywood has long been thought of as a boys’ club. But in actuality, women were the early forces behind the camera from the era of silent films through to the 1950s. It was only after the industry began to consolidate around a few leading production studios that the opportunities for women began to wane. And though there are still challenges (e.g., there were no female directors nominated for a Golden Globe this year), the reels are definitely changing. Enter Olivia Wilde, who while directing her first feature film, Booksmart, brought as many talented women to the table as she could, from screenwriters and producers to casting directors and actors. Among them was one of the film’s beloved leads, Beanie Feldstein, who in fact did earn her first Golden Globe nomination for her role. Over lunch in downtown NYC, the creative cohorts sit down to discuss the prevailing sisterhood in Hollywood.

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BEANIE FELDSTEIN: Liv, do you remember when we met?

OLIVIA WILDE: Yes. It was at a party in New York that I’d gone to mainly because I knew you’d be there. I’d been tracking you. As a new director, I was trying to figure out how to approach an actor in a way that really gets their attention. Basically, I wanted to have a connection with you before I begged you to be a part of Booksmart.

BF: Oh, it was a really hard beg. [laughs] And look how far we’ve come! You’re on the cover of InStyle’s Badass Women issue, which is incredibly fitting. I wanted to start by asking you about some of the women who’ve inspired you most. I know one of them is Mali Finn, the legendary casting director.

OW: Mali was notorious for having incredibly high standards. I worked as her summer intern when I was 16 and then as one of her four assistants, and the proximity to her taught me everything. She was an antidote to the culture of assimilation in Hollywood. She expected everyone who auditioned to have done the work. And then she’d say to these young actresses, “Why are you wearing that short skirt? Did you think that I’d be a man when you came in?” She was trying to tell them to own their power and not strip themselves of everything that makes them different.

BF: She was actually treating them with respect.

OW: She was, and that’s why she was able to discover great talent. When I started to go on auditions, a casting director once said to me, “Olivia, you’ll be all right because you’ve got a pie face.” And I said, “Thank you.” Then I thought, “Wait, was that even a compliment?” Mali helped me reset my standards at a very important time in my career.

BF: You’ve been pulled up by so many women who have helped you succeed, and now you’re reaching behind you to pull up the next group — something you very aptly call the Daisy Chain, because of your little girl, Daisy.

OW: The Daisy Chain is about wanting to lift each other up. I celebrate it because for a long time women have been told that in order to succeed, we have to push people out of the way. [Producer] Jessica Elbaum was someone who dared me to take myself seriously. There were so many people who said, “Oh, you should direct.” But there aren’t many who will actually help you when you’ve never done it before. Jessica had the confidence in me to put her own reputation on the line by recommending that [production company] Annapurna hear my pitch for Booksmart. And that’s real generosity.

BF: Well, Jessica knew you could effing do it!

OW: That’s why daring someone to take themselves seriously is awesome. I pivoted my career from acting to directing at 27, and I directed my first feature at 34. A pivot can happen at any age. There are a handful of people in our movie cast who I know could direct one day, from Katie Silberman, our awesome screenwriter and producer, to Kaitlyn Dever. I want to make sure that happens for them. And then, Beanie, you’re someone who doesn’t need the dare. You inspire me so much.

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BF: Just watching you on the set of Booksmart was that dare for me.

OW: And that’s how [director] Reed Morano was for me on the film Meadowland. She was the first female director I worked with, which is nuts. Honestly, I mourn the years I wasn’t working with any women. As Geena Davis says, “You can’t be what you can’t see.” And once I saw Reed hoist up that camera and operate the film herself, it just cleared the way for me.

BF: When I watch you direct, you’re so confident. Where does that come from?

OW: Steven Spielberg has said that as a director, you must never let an actor see your fear. And I actually think that allows you to manifest confidence. It’s like when I’m with my kids and there’s turbulence on a plane, I’m the first one to say, “This is great! This is fun!” And then I actually feel calmer.

BF: What’s been the best career advice you’ve received?

OW: Make the things that only you can make. Once it’s in your hands, it will be different from everyone else’s work. Fellini wasn’t protective of his scripts. He’d say, “I’ll send it to you, but you won’t make my movie.” I love that concept because it leads you to a place of creating something original.

BF: What was it like growing up with a mom [journalist Leslie Cockburn] who has had such a brilliant career? Just a year ago she decided to take a bold leap and run for Congress.

OW: My mother achieved greatness at such a young age. She was one of the first women admitted to Yale, she became a journalist at a time when women had to work really hard to rise in the ranks, and, at 65, she decided to run for the House of Representatives in the 5th District of Virginia, a position that has never been won by a woman. She gave it everything, and when she lost, she was still so graceful. She’s broken through so many glass ceilings that it was never a question of whether it was possible for me.

BF: And now you’re passing the same thing on to your kids, Otis and Daisy. You told me a great story about Otis and his pride when he said, “My mom is a director.”

OW: I see that it affects them. But for me as a mother, it’s such a balancing act. Like, you filled me with so much confidence, but you didn’t let me become a fucking asshole. When I said I wanted to act at age 3, my mom was like, “Great, go to school for it.” She always took my dream seriously because she’s taken her own dream seriously.

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BF: You went to an intense academic boarding school [Phillips Academy in Andover, Mass.], but then you didn’t end up going to college. Does that decision linger in you at all?

OW: A lot of people say, “I’m the first person in my family to go to college,” and I always joke that I’m the first person in my family not to go. I was eager for life experience. And there was such pressure to start young as an actress.

BF: It’s still the ideology that prevails in Hollywood.

OW: I remember meeting Scarlett Johansson at a party when we were 16. She was already making movies, and I was like, “Ugh, I’m so behind.” So, I leapt into work. By the way, Jason [Sudeikis, Wilde’s partner] didn’t go to college either, so we’re already prepared for our kids to say they don’t want to go. I’ll carry my own baggage into that conversation when I encourage them to go.

BF: The feminist journalist Caitlin Moran has said she had to fight to prove that she was not just a brain because, growing up fat, she was never looked at as a body. You’ve suffered the opposite problem, which is that the world often looked at you for your body first.

OW: That feeling of being misunderstood starts in adolescence. In high school, people place definitions on you, and then you spend your adult life slowly unraveling them. People always resented that I wouldn’t pick a lane. And a lot of the fiery passion in Booksmart was my answer to that.

BF: You’ve also said before that Booksmart was the first job you got that was not based off your looks.

OW: It’s not that I felt I had never been hired in any way for my brain. It was that as a director I finally felt that I was being listened to because of my ideas. It was the first time my brain had been isolated as the valuable element, which was satisfying.

BF: You have a bunch of new directing projects coming up. What are you most excited about?

OW: My film Don’t Worry, Darling is a leap of faith because I’m putting myself in the film, which is madness. I took so much pleasure in removing myself from the process, so now I’m very curious to see how I’ll be able to take care of everything from within.

BF: How much sleep do you get a night?

OW: About five hours. It’s forever a process of trying to find the balance. For me as a mom, time becomes essential, because there’s so little of it when you are focused on keeping people alive. Then the time that’s left for you becomes very potent, and you can achieve great things with it. I do like the idea of relaxing, but my best ideas don’t come from those moments of rest. I get those when I’m jumping on the subway and racing to a meeting.

BF: How are you raising your kids to be strong and independent?

OW: With Daisy, I have witnessed how women are born with an incredible amount of strength and that society quickly pushes them to assume the more feminine role. I mean, I love that Elsa is looking pissed off on the Frozen 2 poster, but there’s still an awful lot out there that’s encouraging young women to make themselves the weaker sex. My role is to be a safe zone of support that’ll hopefully counteract what society will inevitably do to them. When Daisy hits a place where she questions her worth, I want to be the one to remind her of the strength she innately has. But it’s interesting because having a boy and a girl, you really notice gender politics within your own home. She’ll clean up his plate for him after dinner, and I’m like, “Put that back!”

BF: I also want to ask about your personal style, because I know for a fact that yours has changed a lot. When you moved to L.A., you used to wear yellow turtlenecks to pool parties, and that’s why my character, Molly, wears one in the opening of Booksmart.

OW: That’s right! I’d wear wool turtlenecks. It didn’t matter how hot it was.

BF: So how does style come into play in your life now? You had a different pair of incredible sneakers all 26 days that we shot our film.

OW: My stylist, Karla Welch, is one of my best friends. She knows I love a strong shoulder and anything that makes me feel powerful. That doesn’t mean I don’t love a flowy frock here and there, but you learn what makes you feel like your best self.

BF: My mom actually texted me this morning to say that you looked amazing at the Gotham Awards.

OW: Your mom is my everything. I was wearing this ridiculously long Miu Miu dress, and I was laughing because I’m not good at altering the way I move in the name of fashion. Everyone was like, “Olivia, you can’t stomp around like Seabiscuit!” But tripping over my dress was worth it if your mom loved it.

BF: I have to say the most surprising thing I’ve learned about you is that you love a low-rise jean. It’s something that I don’t quite understand because I want the top of my jeans to touch my bra strap.

OW: I’m still pretending to be a teenager from the early aughts. My most comfortable state is when I’m wearing low-rise jeans, sneakers, and a sweatshirt. In that, I am unstoppable. And if I’m in a high-waist jean, I can’t let my gut expand. When I see pictures of people like Paul Feig directing in full-on outfits, I’m like, “How?”

BF: Last question: What does the word “badass” mean to you?

OW: If you had asked me this a few years ago, I would have said, “Oh, I’ve been skydiving. I have tattoos. I’m ballsy.” But hands down, directing a movie is the most badass thing I’ve ever done because it is the scariest thing I’ve done. It forced me to tap into my inner strength, and you know what? That may be the most badass thing of all.

Photos: Pamela Hanson/LGA Management. Styling: Karla Welch/The Wall Group. Hair: Lona Vigi for Starworks Artists. Makeup: Mélanie Inglessis for Forward Artists. Manicure: Ashlie Johnson for The Wall Group. Set design: Daniel Horowitz for Jones Management. Production: Kelsey Stevens Productions.

For more stories like this, pick up the February issue of InStyle, available on newsstands, on Amazon, and for digital download Jan. 17.