Olivia Wilde Wants Us to Take a Closer Look

Famed film figure goes behind the lens with directorial debut

Olivia Wilde has wanted to direct movies at least as far back as 2003, when she began acting at age 19. “When I was on set, I found myself drawn to the cameras,” she says, recalling the desire to explore the cathartic experience of acting from the other side of the lens.

Wilde then took every opportunity to give herself what she calls “the film school education I never had.” In the ensuing years, she directed a short film and a pair of music videos, and produced a handful of projects in which she also starred.

After years of attending SXSW Film as an actress, Wilde is thrilled to return this year as the director of the feature film Booksmart, a high school comedy about two best friends who decide to spend the evening before graduation cramming four years of partying into one wild night. “My dream since we were shooting this movie was to premiere at SXSW, so this is a huge deal for me.” Wilde explains.

“I remember feeling like it was this great sort of life moment of knowing that I was really proud of something that I had achieved,” she recalls about her past visits to the festival. “SXSW has this significant place in my life as a marker of evolution.”

Olivia Wilde. Courtesy of Sam Jones Pictures

Olivia Wilde. Courtesy of Sam Jones Pictures


“We’re in that crazy stage where the egg is just hatching,” says Wilde, who is equal parts nervous and ecstatic about the upcoming World Premiere of Booksmart. “It’s been this private project for so long, and now we’re about to birth it into the world.”

In addition to debuting Booksmart, Wilde will also be appearing at SXSW as a Film Keynote. “It’s incredible,” she says. “For the first time in my career I feel that I’ve earned the right to impart my wisdom upon an audience.”

The most important lesson Wilde learned while making her first feature? “You can’t have everything that you want,” she says. “You have to be a sort of reckless dreamer in order to be a director, but you also have to understand the reality of the restrictions involved,” and, more importantly, “you have to embrace those restrictions.”

The process of working through and around these limitations, Wilde says, is “how you’re going to discover other awesome things that you just never would have considered had you not had to redirect based on a sacrifice.” At the same time, she says,

“You have to love your project so much that literally nothing can stop you from making it.”

Wilde is particularly excited to share her knowledge with aspiring filmmakers — especially young women, who often have to fight to make the same leaps as their male peers. “I certainly feel like there’s this huge swell of enthusiasm for female filmmakers,” says Wilde. She cites Chloe Zhao and Reed Morano (“One of my very best friends,” Wilde says) as examples.

Zhao landed a coveted gig directing a Marvel superhero movie on the strength of her 2017 indie, The Rider. Morano, who directed Wilde in the indie drama Meadowland and serves as executive producer on The Handmaid’s Tale, is directing Blake Lively in the blockbuster spy thriller The Rhythm Section, from the producers behind the James Bond franchise. “That’s the kind of leap that women have been unsure of,” but, Wilde offers, “I’m seeing more women make that jump — and finding the confidence to take that huge leap more often than they were before — because of this movement.”

Kaitlyn Dever and Beanie Feldstein from Booksmart premiering at SXSW 2019

Kaitlyn Dever and Beanie Feldstein from Booksmart premiering at SXSW 2019


Wilde worked hard to ensure that the cast and crew of Booksmart were as diverse as possible. “In order to really shift the paradigm,” Wilde says, “we’re going to have to change the way that we hire women, and hire people.” She credits Annapurna Pictures with giving her total control over hiring: “The studios have to trust the filmmaker to hire the department heads that they trust instead of just hiring people because they know them and have worked with them before.”

She also credits her casting director, Allison Jones, with helping her find “a really diverse and fairly representative cast” of young actors, including several newcomers. Jones’ approach, Wilde explains, was simply to find the best talent available: “It was so organic.”

As for what she hopes audiences will take away from her directorial debut? “If I could ask for one thing when people walk out of Booksmart is that they feel seen,” Wilde says. “And that they are eager to see others a little bit more.” Wilde cites one of her favorite moments in the film, when the character Molly is giving a graduation speech. She looks out on the crowd of classmates who, up until the night before, she was so quick to judge and neatly categorize into little boxes, and says “I see you now.”

“That’s really what I want desperately for the world, to take a deeper look at each other,” says Wilde. “That, at the heart, is what the story is about.”

Olivia Wilde was a Film Keynote speaker at the 2019 SXSW Conference on Monday, March 11. Watch it below:

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