With Directorial Debut ‘Booksmart’, Olivia Wilde Addresses Underestimated Demographic Of Young Women

Anthony D'Alessandro

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After playing determined free spirits who refuse to be boxed in, like Quorra in Tron: Legacy, Devon Finestra in HBO’s Vinyl, and ambitious Atlanta Journal-Constitution reporter Kathy Scruggs in this season’s Richard Jewell, Olivia Wilde expanded her résumé, which already included producing Meadowland and A Vigilante, to make her feature directorial debut with revisionist teen comedy Booksmart. The pic follows two brainy high schoolers played by Beanie Feldstein and Kaitlyn Dever who realize they have only 24 hours before graduation to finally let loose. What ensues is a comedic caper packed with poignant musings on friendship and identity.

While the pic, like many smaller films this past summer, was bulldozed by Avengers: Endgame and Aladdin, it spoke to its core audience, and Wilde impressed studio executives around town to the point where they were clamoring and bidding on her follow-up directing projects with Booksmart writing collaborator Katie Silberman: the elevated genre project Don’t Worry Darling, which New Line won, and an untitled holiday comedy for Universal.

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DEADLINE: Booksmart was on The Black List for a long time. Why do you think it took so long to get made?

OLIVIA WILDE: I think the reason it hadn’t found its home was because in many ways, society wasn’t yet ready for it. I think many times, the world has to catch up with a concept before the movie can be made, and I think for this one, it was just simply that we were waiting for a time when audiences would really be ready for this story, and it would answer a question on everybody’s mind, which I think it has.

I think that the question resulting from what happened in the 2016 elections and everything since is: What are women capable of, and when are they at their most powerful? And the answer is, of course, when they are linked, when they work together, when they collaborate, when they support each other. And so, this concept suddenly felt like it was scratching that exact itch.

DEADLINE: Tell us about meeting screenwriter Katie Silberman. What dynamic did she bring to the rewrite?

WILDE: [Booksmart producer] Jessica Elbaum sent me Katie’s Set It Up screenplay and I laughed so hard, and just fell in love with her through her writing. And then, when I met her, I asked the same question I had been asking other writers, potential collaborators: What would you do to this script to not only raise the stakes, but to introduce the concept that this movie should be about feeling seen and seeing others?

I wanted to make this about judgment, and what can we do to flip the tropes on their back, and her very simple and brilliant answer was: What if all the other kids were smart, too? I’ll never forget that moment where I was like, “You’ve cracked it, that’s it.” Everything else flows from that revelation. So, based on that first conversation, I knew that we had a really organic shorthand, and I knew that we understood each other’s styles really well, and the process was truly effortless.

DEADLINE: What lessons have you taken from directors you’ve worked with over the years, like Reed Morano, Martin Scorsese and Spike Jonze?

WILDE: The biggest lesson is to allow for that constant evolution of your ideas, to continue rewriting as you shoot, as you edit, as you sound mix, to allow everything to continue to evolve. And I think just hiring the team that allows for that, delegating well, and allowing for the respect for the artists you hire to be so great that you can embrace ideas that are not your own, and personalize them, and incorporate them into ideas that are.

There’s a fluidity to that evolution, but in terms of more concrete ideas, I think listening to your instincts, and fighting for your ideas, knowing when to really throw down and fight for your ideas. You know, there are three scenes in Booksmart that I was encouraged to cut until the very end, and I’m glad that I didn’t, but you really do have to know what’s worth fighting for, and know what isn’t working.

DEADLINE: What were those three scenes?

WILDE: The stop-motion animation scene, the dance fantasy and the pool scene.

DEADLINE: The last one was your most ambitious scene to shoot.

WILDE: Yes, incredibly, incredibly hard to shoot. That scene was a sort of guiding principle. I love magical realism, and what I was trying to bring into the film, in all three scenes, was a chance to enter into the internal world of this character, and to really lean into the kind of impressionistic perspective of adolescence that she would have in that moment.

[With the underwater scene] we were shooting in the house where the big party takes place, and then I had the water unit working in the pool. So, I was running back and forth between the two units, but I knew that the pool moment was my baby. That was kind of my obsession, that scene, and I knew that we would have to get enough footage to build this moment, this concept, and this idea.

And so, we roamed around at the bottom of the pool, we let the camera roam around and capture these moments, both of Kaitlyn and then her POV, and we shot for a few hours to get what you see. Originally I had a two-and-a-half-minute version of that scene that of course I felt really worked, and it was absurdly long; it was basically the entire Perfume Genius song, and then I thought, Wait a minute, I’m being a little bit indulgent here.

DEADLINE: What did you want people to understand about Booksmart’s target demographic of women under 25?

WILDE: It’s fascinating to me, because they are such a discerning demographic, and they have so many options and they don’t want to be underestimated and patronized. I feel that what we were able to tap into was the intelligence of this demographic, who felt like they wanted to see a story about their lives. They wanted to feel represented onscreen but no longer put in a box of a superficial obsession with boys, or assimilation to pop culture.

There was a certain sort of wisdom beyond their years that Beanie and Kaitlyn’s characters of Molly and Amy represented. I feel that tapped into what we’re seeing now in these young women who are so much more mature than at least I was at that age. I think because of Trump, and because of social media, there is a fast pace to the aging, the growth, the evolution of these young women, and by the time they’re 15, they understand their identity in the world, their political identity, their feminist identity, in a much clearer way than past generations, or at least generations since maybe the Sexual Revolution. There’s now a sense of having to own your voice and define it, and I think this film felt like it was acknowledging that shift.

So, you know, it’s still completely impossible to grab everyone, and of course, our box office numbers weren’t what maybe a film like this could’ve garnered 10 years ago, when it was possible for you to target your audience and bring them into the theater. We could go on for hours about what went wrong in that sense, but I do feel that what I noticed was a kind of grassroots campaign by our audience that started after the film’s release that I was really struck by, and kind of moved by, when I saw young women saying, “This is a film for us. This is something new, and something we have been looking for.” And then, what moved me beyond that was that the men were feeling that way—young men, older men, older women, younger, all genders, all races, all ages feeling represented by this film. I think what I learned from that is that when you are very specific, you can actually cut through the fabric of society and feel authentic, and feel worth watching.

DEADLINE: After Booksmart’s release, studios were fighting over your new project Don’t Worry Darling and your untitled holiday comedy. How did it feel?

WILDE: It was extraordinary and unexpected. The groundswell of support and enthusiasm was extraordinary. I didn’t expect it. I didn’t know what to expect. I just hoped I’d be able to direct again, and this was even before the release. You know, just finishing the film, I thought, I want to do well enough that I get to do this again, and then, when I did feel an incredible amount of curiosity about what I wanted to do next, and a lot of offers coming my way, I was encouraged. Because there is, of course, a pattern in Hollywood of particularly women not being given an opportunity to make their second feature, if their first doesn’t score at the box office. So, so many female directors had one chance, and they aren’t given another chance as rapidly as the men are.

So, when I felt all the support, I was so encouraged to witness what I think is a sign of change in our industry. I felt that I was being given an opportunity that many male directors, frankly, have been given, a chance to do it again. And I felt that this was a sign that my work was being appreciated not because of box office numbers, but because of the effect that it’s having on audiences that did get to see it. And so, it was entirely shocking, and also really encouraging, and I hope that it is a sign of things to come.

I hope that all of my female directing peers are sensing that same shift, that the ability to continue working is not predicated upon box office, but rather skill, [that] meritocracy is working the way it should.

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