Olivia Wilde on Her Move From Acting to Directing With ‘Booksmart’

Olivia Wilde began acting in 2004 when she was 20 years old. It never occurred to her that she might also enjoy stepping behind the lens.

“I always wanted to make movies and be a part of the moviemaking process,” she tells me. “I always assumed acting was the way in, because for many young women … they’re told, ‘You love movies — you should be a movie star.’ No one tells a little girl, ‘Why don’t you become a director?’ It’s just not a part of the conversation. But if a little boy says he loves movies, it’s like, ‘Maybe one day you’ll direct. Maybe you’ll be the next Steven Spielberg or Martin Scorsese.’”

The lack of gender parity in directing was front and center when the Oscar nominations were announced on Jan. 13. All of the nominees in the category are male. Greta Gerwig (“Little Women”) and Lulu Wang (“The Farewell”) were considered strong contenders but were shut out by Academy voters.

Wilde was also a contender early in the awards season for “Booksmart,” her feature film debut about two straight-A high school seniors (Beanie Feldstein and Kaitlyn Dever) who decide they want to have at least one wild night of partying before graduation. “Booksmart” may not have made it to the Dolby, but it was a critical hit and has a 97% score on Rotten Tomatoes. A true sign that the movie resonated and became a pop culture phenomenon: Young people everywhere dressed in costumes inspired by Feldstein and Dever’s characters for Halloween.

Unlike the Oscars, the Independent Spirit Awards’ nominees are a much more diverse group. That’s where Wilde will be on Feb. 8. She is one of two women directors — Laure de Clermont-Tonnerre (“The Mustang”) is the other — up for best first feature, along with Michael Angelo Covino (“The Climb”), Kent Jones (“Diane”), Joe Talbot (“The Last Black Man in San Francisco”) and Stefon Bristol (“See You Yesterday”).

Seeking guidance from mentors like her “Meadowland” director Reed Morano was key to Wilde’s ability to get “Booksmart” greenlit by Annapurna. “She said, ‘Pitch your heart out. Pitch the movie you want to make, not the movie you can make. Just pitch the most ambitious plan,’” Wilde says. “What I have noticed is what female directors do to ourselves — we will pull our punches too early. We say things like ‘This is probably financially irresponsible, so I could probably make it something simpler. This feels more doable.’”

But doable isn’t good enough.

“Reed said to me, ‘No one is going to buy the thing that you sell as doable or sufficient,’” Wilde says. “Someone is attracted to the filmmaker who has such ambition and such lofty ideals for what their film could be. [Annapurna] could tell I was chomping at the bit, that I wanted to tell this story. They allowed me to take this on and make it my own.”

That included casting an ensemble of young people — some of whom had never acted — who represented a rainbow of cultures and communities, something lacking among the current crop of Oscar nominees. Cynthia Erivo (“Harriet”) is the only actor of color in the race.

“We removed the barriers that keep most people out of the process,” Wilde recalls. “We didn’t have a studio saying you have to cast a star. We didn’t have a studio saying they had to look a certain way. No one asked how many followers they have on social media.”

When Wilde looks back on her early days of acting, she realizes that she craved exploring a wide variety of genres. So it’s no surprise her credits range from the sci-fi adventure “Tron: Legacy” to the improvised indie “Drinking Buddies.”

“I never wanted to pigeonhole myself,” she says. “I was just like, ‘I love everything. I’ll do anything.’ That was evidence that what I really love is the process. That was a clue that I was supposed to be directing.”

Next up for Wilde is directing and starring in “Don’t Worry, Darling,” a thriller about a woman who may be losing her mind. “The most apt way to describe it is as a psychological thriller for the Time’s Up era, because it does touch on the larger themes that women are grappling with at this point, which are: what is the patriarchy and how much do we actively participate in it and rely on it.” 

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