Stepping into the director’s chair for her first feature-length film, Booksmart, Olivia Wilde realized that her own education on movies and television productions over a flourishing 15-year career as an actress had more than prepared her to move behind the camera.
“What changed in me was a realization that I have in fact learned something, and that this is a pivot for me that I feel very ready for,” Wilde told The Hollywood Reporter at a special screening of her debut effort at the Theater at the Ace Hotel in Los Angeles.
The coming-of-age comedy features a pair of rule-following, overachieving high school best friends (played by Beanie Feldstein and Kaitlyn Dever) who try to squeeze in one huge night of finally cutting loose with their classmates before moving on to college. Unlike her lead characters, Wilde was surprised by just how fully prepared she was to step out of her own comfort zone.
“Sometimes you don’t realize how much you know until you’re teaching someone, and I think that was a real aha moment for me,” she said. “I realized how much experience I’ve actually had in this business, and I was able to impart some of that knowledge to this young cast. Whether it was by having a no sides on set policy, which I stole from Scorsese – it’s just a really great way to arrive prepared and ready to create – to playing music all the time, like I had experienced on many different directors’ sets, learning from people like Spike Jonze and Ron Howard and Jon Favreau and Reed Morano, people who I just love and admire.”
Wilde’s technique inspired a similar amount of respect from her cast. “She’s not only an actor, but she’s also a producer, and she’s also an activist, and I think what she really picked up on in this current generation is how engaged young people are,” said Feldstein, who plays Molly. “Young people today are living in society; they don’t really have a bubble around them. They are a part of the conversation, they’re politically engaged, they’re socially engaged. She really understands that, she respects it and she admires it, and she wanted to celebrate that in the film.”
“From the moment I met Olivia, we’d be talking about our high school experiences,” Feldstein continued. “We both went to really rigorous academic high schools and had a very, kind of like a Molly and Amy-esque, high school experience, with how much pressure was put on us and how we internalized that pressure, so there was no better person to do the job. And she’s also so brave in her directorial choices. They’re just bold and unapologetic, in the same way that the two leads are.”
Dever, who plays the more reserved but eager-to-bloom Amy, said she admired Wilde’s “deep understanding for what it’s like to be young. She really, really gets it. She really gets life on a deeper level than I ever will. She really understands people and how a movie can move you in so many different ways. I think Booksmart does exactly that: it’ll make you laugh, it’ll make you cry. It’ll make you feel giddy inside, it’ll make you feel nervous, it’ll make you scream. It’ll make you feel a lot of things, and I think that is all because of her. She’s an unforgettable person.”
“Every day she was just so excited to be there, got there early, stayed late, just got in the trenches with us in a way that only actors can do,” said co-star Billie Lourd. The steady flow of music and a copious supply of quality snacks were also part of Wilde’s tactics. “Olivia was walking around with a speaker the whole time,” Lourd added. “I felt like I was at a house party – except the beer was non-alcoholic. And she’s just like the most humble, lovely human to be around. Honestly, like, what can’t the woman do? She set the bar so high.”
“She set a tone where there was no hierarchy,” said Katie Silberman, one of the film’s screenwriters. “Everyone was as valuable as everybody else, and everybody’s ideas were as valuable. But she also really took the time to understand each part of the craft – she knew more about cameras, about props, about costumes, about hair, than any director I had worked with. And so she not only took the time to understand that, but then connected with each of those departments and made them feel a part of the story.”
One of Wilde’s most unexpected moves was suggesting that Feldman and Dever become real-life roommates to deepen the onscreen bond their roles required.
“When you’re put in a movie and you’re given a best friend, you don’t usually get the time you would normally have to create a bond with someone in real life,” said Dever. “For someone like Olivia to be like, ‘Yeah, you guys should live together. Go do that,’ It was like, ‘Oh – we can? That’s great!’ And it allowed me and Beanie to get to know each other on a deeper level…. Both of us were able to rehearse all the time, go over our dialogue and just get to know each other. It was the best thing ever.”
“Oh my God, it was immeasurable,” agreed Feldman. “With your friends, you have no boundaries. You have no politeness. You have no formalities. You’re sort of one person in the way that you interact and finish each other’s sentences.”
Along with co-stars like Lisa Kudrow and Wilde’s husband, Jason Sudeikis, an array of her Hollywood circle of fellow celebrities turned out for the screening in support, including Will Ferrell (who served as one of the film’s producers), Kristin Wiig, Jonah Hill (Feldstein’s brother), Busy Phillips, James Marsden and Lakeith Stanfield.