The roiling waters of teenage life are a universal constant, but Booksmart quickly drops anchor in the here and now. It’s all there in the movie’s opening scene: the framed Ruth Bader Ginsburg photo, the night guard of the anxiety-addled teeth-grinder, the mindfulness app (voiced, if only they all were, by Maya Rudolph). “Good morning, winner. Take a deep breath,” the voice coolly instructs Molly, the overachieving class president (Beanie Feldstein). “Fuck those losers.”
What are the modern gospels, if not wellness and empowerment overlaid with a little Ivy League–bound perfectionism? Leave it to first-time director Olivia Wilde—a boarding-school alum turned Hollywood go-getter—to sketch a humanizing, wisecracking portrait of high school with an unshakable female friendship at its core. Sitting in a sunlit booth at the Manhattan restaurant King on a recent afternoon, Wilde considers how Booksmart reflects a generation that is “so evolved, so fluid, so in tune with the significance of their voices,” the 35-year-old says. “I keep thinking about how, when I was a teenager, being political was a choice, as opposed to everyday life and everyday decisions [now] being inherently political.”
For Wilde, working with an all-female group of screenwriters is political. Orchestrating a sex scene geared around respect (without sacrificing humor and titillation) is political. So is cleaning up the skin-care space—something she thinks a lot about as an ambassador for True Botanicals. There’s a reason that the natural skin-care category has become fertile ground for female entrepreneurs (True Botanicals founder Hillary Peterson included): when women are the target market in an industry long beset by punishing beauty standards and possibly harmful ingredients, the need for improvement is obvious. The connection between the two worlds—onscreen, on skin—might not be apparent, but Wilde makes a case for it. Ahead, she talks about presenting sexuality from the female point of view, the wild west of CBD, and why Jason Sudeikis is immune to the charms of her very nice smells.
Vanity Fair: Misguided perfectionism is a theme in Booksmart. Did that resonate in some way with your younger self?
Olivia Wilde: I think we all go through a shift after school where you wonder, Without grades, how will I know how I’m doing? I had to learn that my value didn’t necessarily come from accomplishments that were easily graded on paper, but they were potentially a little bit more subtle and more internal. So I approached going to Hollywood at 18 like a project. I was working as a casting assistant, and I said, “If I don’t succeed in nine months, then I’ll go back to college.” I was going to study theater at Bard in upstate New York. It was at once kind of flinging myself out there into the world with reckless abandon, but also very thoughtful. I had high standards for myself.
Was there ever a time that it felt too intense?
It was all leading to a point when I was 26, when my world had kind of fallen apart. I’d gotten divorced. My career felt kind of chaotic and unsatisfying. I was being hounded by paparazzi. I was just really unhappy. A good friend of mine said, “Doesn’t it feel good to not have to be perfect?” And I remember this moment of relief where I realized that, without knowing so, I had forced that upon myself. From that point on, I allowed my flaws to just be space to learn, and the humility that came with that period of my life taught me a lot more about who I am. So the movie takes the position that that happens to these girls in one night at 17. It took me 10 years beyond high school to really understand that.
Did you face the usual teenage pressures in terms of beauty norms?
I was hopeless! I yearned to achieve those standards, and yet it was never my natural way. I was always just a little—messy is the wrong word, but more chaotic. I still haven’t ever learned to blow dry my own hair. I remember watching my roommate in boarding school do her eyeliner meticulously every morning; I was in awe and I still am. So I leaned the other direction. I embraced a kind of bare, casual standard for myself.
Any beauty regrets from that time?
So many things. When I was 12, I went through every color in the entire Manic Panic line—even that kind of puke orange. And when I was 13 or 14, I just plucked off all my eyebrows. Everyone else’s grew back except mine. I had to blade them back in. I regret going to a tanning booth when I was in high school. It was a standup one, which is the creepiest thing in the world, and I remember having those weird goggles on and really knowing deep down inside that this is a terrible mistake. It’s such an awful thing, and luckily I didn’t do it again. I went through all the very stereotypical high school experiments: really bad highlights and really straightened hair.
Tell me about the line in the script that the two leads—Beanie Feldstein and Kaitlyn Dever—wanted to change. I’m curious what you wound up learning from them during filming.
It’s the scene towards the beginning, when they’re on the hilltop, and Molly’s convincing Amy to go [to the party]. It used to be: “You’ve been out for two years, and you’ve never had a lesbian experience. I want this for you.” And they were rehearsing, and they called me over and said, “Liv, it’s just that we don’t say ‘lesbian experience.’ We just kind of say ‘experience.’ “ And I was like, Oh, is that label just not really necessary anymore? I remember when I played a queer teenager on The O.C., it was all about saying “lesbian,” saying “bisexual,” owning that, and I took it very seriously as a person playing a character. But for the younger generation, they are tossing off labels and just embracing fluidity, which is so evolved. They are incredible young women.
I like how the movie brings up masturbation without the usual stock jokes. It seems in line with the conversation around female sexual health now—while also being flat-out funny.
Yes! It was an attempt to really reflect how women actually speak to each other. I kept thinking about how, when there are rated-R comedies starring women, often you’ll hear dialogue written for guys put in the mouths of female characters. And so people can say, “This is so great. They’re joking around like dudes—women are funny!” Well, that’s bullshit because women are funny in a very different way. I wanted to have the women talk the way girls do about sex and masturbation, and the actresses really embraced that. They loved the idea that their characters could be inexperienced sexually but still be extremely sex-positive feminists.
How then did you approach the sex scene?
It was finally my chance to direct a sex scene the way that I always wished I had been directed in a sex scene. I created an actually closed set because, most of the time, there are still unnecessary people in the room. It was kind of extraordinary to feel like I was providing something that I had always wanted someone to give me—a real sense of safety—and to allow them to relax. And it was a chance to show that the sexiest thing is to not show a lot of nudity. It’s all about Kaitlyn’s face as she looks down. We don’t see what she’s looking at, but she’s so brilliant that we feel she’s looking at a naked woman for the first time. I really loved being able to nurture the girls in that environment. There are just things that I didn’t know I could ask for as a young actress, and I wanted to tell them not only can you ask over these things, you should protect yourself without shame. You’re not being difficult.
I reached a certain point in my life when I understood that I wanted to take care of myself in a way that didn’t mean make myself more beautiful to assimilate. It’s sort of an understanding of my own value and taking care of my well-being, my body, my mind. I think if I had known at an earlier point in my life that I was worth that kind of self-respect, [I might have done things differently]. Not saying, Well, in order to reach these standards of beauty, I have to do these things that I know are bad for me.
It makes the topic of beauty inherently political, when you consider an industry that’s been historically problematic, through messaging or ingredients.
Absolutely. If your dollar is your vote, you’re saying, “Attention, giant skin-care companies: I’m now aware of these ingredients and how potentially poisonous they are. I’m going to support companies that are using an alternative route.” And then those larger companies will be forced to respond.
What do you make of CBD, in terms of the promise and the unknowns? It’s the wild west out there.
In my personal experience, I think CBD is an extraordinarily effective natural alternative to so many different medications. It’s an example of us getting in touch with a natural element, a botanical, that is often ignored and vilified. I want results, and I want it without poison. That’s why thoughtful sourcing is so important. It’s something that consistently makes True Botanicals unique, and why I have so much respect for Hillary [Peterson]—because her standards are so incredibly high.
Aromatherapy is another focus of True Botanicals. But is it true that Jason [Sudeikis] can’t smell?
That’s true! He can’t smell, and I smell so good all the time—it’s wasted! I walk through the house, and I’m like, “Trust me: I’m spreading the most amazing essential oils everywhere.” But it’s interesting: I’ve talked to a neurologist on his behalf about it, thinking, if aromatherapy can be so healing and actually dramatically effective, then what happens if you have no ability to smell? Is he missing out on something? The mental health angle is so important because, really, the self-care element comes from an internal space.
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