For her first shot at directing, in the funny, charming Booksmart, Olivia Wilde chose a movie about characters she could relate to — young women who chose to succeed where success can be quantified and who don’t waste time worrying about being liked.
The comedy follows two Ivy League-bound high school seniors (Kaitlyn Dever, Beanie Feldstein) who decide after four nose-to-the-grindstone years to go on a deferred party spree.
They’re very driven young women, and Wilde had that in common with them, but she admits she didn’t live up to their standard as straight-A high achievers.
“My history as a student isn’t as spotless,” said Wilde, laughing. Now 36, she attended some private prep schools and was admitted to Bard College but put off attending, permanently, when she was able to find regular work as an actress (she made a memorable splash in The OC).
“But within my career, I do have a kind of relentless curiosity and intensity, and I do love to learn from the best,” said Wilde, who over the years has picked the brains of Spike Jonze (Her) and Martin Scorsese (Vinyl). “Also, I don’t have much patience for people around me who aren’t taking their work seriously.”
What she noticed was that men like Scorsese and Jonze don’t waste time on the set wondering whether everybody likes them. Scorsese in particular (“I completely stole from him”) likes actors to show up fully prepared and on point so the serious work can begin.
That lack of concern over likability is a skill many women have to learn, Wilde said, and it’s partly why she connected with the characters of Molly (Feldstein) and Amy (Dever) in Booksmart. They see school as being about proficiency, not popularity.
“I have a bit of Molly and Amy in me. And [Booksmart] was just a nice opportunity to explore the kind of multidimensionality that women contend with. Sometimes, women struggle to be understood, specifically on the issue of likability. It’s a constant female struggle. You see it high school, and you see it in politics,” said Wilde, whose parents are in the news business — mother Leslie Cockburn was a producer at 60 Minutes, father Alexander Cockburn is a columnist and essayist who writes about politics and economics.
She was about to digress into an analysis of female popularity as it relates to the Democratic field of candidates, but time was short, so we moved on with Booksmart,
“These are undoubtedly really intense people, Molly and Amy. They are relentlessly articulate and ambitious and curious, and they have very high standards for everyone around them,” Wilde said. “What they are struggling with is how their peers are seeing them.”
They are self-confident and supportive of each other, but the insularity of their friendship, and the lonely-at-the-top landscape of their achievements, has them on the cusp of graduation wondering whether they’ve missed something.
Early scenes in Booksmart show them trying to figure out how to be more socially adept. They tackle the subject with problem-solving brains, heading to a party with the detachment of anthropologists studying an exotic population to see what can be learned.
The process is especially fraught for Amy, Dever’s character, who is gay. This is known to the school and to her parents (Lisa Kudrow, Will Forte), but studious Amy has never had a date and sees the party as a chance to maybe meet someone, setting in motion one of the movie’s durable teen-comedy mechanisms.
One of Wilde’s goals was to deliver a teen comedy with some familiar structure and beats but to update it in a way that would accommodate modern culture. She researched teen attitudes toward sex formally and informally, talking to as many high school students as possible to gauge attitudes.
Wilde found what she saw as a significant generational difference in the way people look at gender and sexuality, which informed the way she presented Amy.
“First of all, what could be more universal to a teenager? You have feelings for someone who doesn’t know how you feel about them. And we were really eager to tell a story that reflected that. Whether you are straight or queer or anything in between, the experience of having a high school crush is known to everyone,” said Wilde.
At the party, Amy is just another kid having mixed-signal misadventures.
“I think [Booksmart] reflects how fluid young people are today, and I was inspired by them. They’ve rejected the binary terms we use, and they’ve just said, ‘Look, we’re going to think about it differently,’” she said. “And, by the way, no one is saying, ‘Give us credit for this. Look at our wokeness.’ It’s effortless. When I speak to these people, I realize we [older generations] are dinosaurs.”
As are, increasingly, folks in Hollywood who have rigidly defined roles for people like Wilde and other actresses, like Greta Gerwig (Lady Bird) and Elizabeth Banks (Pitch Perfect 3, the forthcoming Charlie’s Angels reboot), who’ve turned to directing, taking charge of sets and their careers.
She’s not ruling out acting work, but she has nothing scheduled at the moment, and she’s hard at work on another script with Booksmart cowriter Katie Silberman that she’d like to direct.