Olivia Wilde on Her No Film School Fears, Clint Eastwood’s Advice, and a Secret Short

Filmmaker Toolkit Podcast, Ep 107: 5 things we learned talking "Booksmart" with director Olivia Wilde.
Kaitlyn Dever and Beanie Feldstein in "Booksmart"
Kaitlyn Dever and Beanie Feldstein in "Booksmart"
Annapurna Pictures

In the years leading up to “Booksmart,” filmmaker Olivia Wilde had a strong urge to put all that she had gleaned from her years on set as an actress into use when it finally came time for her to direct. When she was a guest on IndieWire’s Filmmaker Toolkit podcast, she admitted that one of the biggest obstacles she faced on her path to making “Booksmart” was her fear over a perceived lack of experience.

“I was so insecure based on my lack of film school training,” said Wilde. “I think that’s what a lot of people say, ‘I would direct, I just don’t know enough about lenses.’ And that’s an excuse, you don’t need an encyclopedic knowledge about the technical aspects of every single element, you need the awareness of what a collaborative experience it is, and the joy is really in hiring those people to help you make it.”

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Wilde’s directing friends, specifically Mark Romanek and Spike Jonze, encouraged her to try her hand at music videos first, which she found to be a great outlet to let lopse her pent up creative energy and gain confidence. “It’s what I imagine would have happened in film school, a challenge: Take a day, and few days to edit, and make something extraordinary and poetic,” said Wilde. “It’s almost like writing a poem to find your voice and visually tell a story, which in itself is its own challenge.”

What Wilde learned while making “Booksmart” was that she needed the confidence in her vision to say to collaborators, “this is a project worth your time and skill,” rather than worrying about being able to make every technical decision herself.

“When crafting a shot I loved acknowledging what I don’t know,” said Wilde. “So that I could allow for that person that did know the answer to feel empowered. That was a fun part for me, to say to the DP, Jason McCormick, who was so wonderful, to say, ‘This is the mood I want here, help me find that mood.'” That’s only the start of what she learned making her feature directorial debut; here’s what else Wilde took away from the experience.

Comedy Advice

Michael O’Brien in "Booksmart"
Michael O’Brien in “Booksmart”screenshot

Michael O’Brien turned in a brilliant performance in “Booksmart” as the pizza delivery man the two leads (Beanie Feldstein and Kaitlyn Dever) try to “hold up.” But the celebrated comedy writer and ex-“Saturday Night Live” staffer also had some important wisdom to share.

“He’s one of the best comedy writers out there,” said Wilde. “And he says, ‘Comedy works like a slingshot, and the further you pull it back the further it will fly, but if you don’t have the courage to pull it back it won’t go very far.’ And you see weak comedies are just like weak sling shots, boom, boom, boom, just dribblling off, but it’s really fun to say, ‘Oh wait, these actors are so good, that we can pull this way back.'”

Eastwood on Directing Yourself

Another person Wilde tapped for directing advice is her “Richard Jewell” director Clint Eastwood. Following “Booksmart,” Wilde’s next big challenge will be directing herself in the thriller “Don’t Worry Darling,”a feature that she is rewriting with “Booksmart” screenwriter Katie Silberman.

“I asked Clint Eastwood, ‘How do you director yourself?’ And he gave me really solid advice,” said Wilde. “He said when you are directing yourself you will under-cover yourself out of shame. So you’re on your own close-up and you’ll move on because you feel like an asshole.” Eastwood told Wilde to make sure not to short-change her own coverage, to give herself another take for her own close-ups.

Wilde, acknowledging Eastwood famously doesn’t like to do multiple takes joked, “Cool, cool. Can I have another take?”

Cutting “Booksmart” Graduation Speeches


While on the podcast, Wilde talked at length about her process of pushing and experimenting with the pacing, editing, and transitions in “Booksmart.” One major change came late in the process.

“When we were sound mixing the graduation scene, there used to be two long speeches, the character of Jared (Skyler Gisondo) had a long speech and Molly had a long speech,” she said. “And I said, ‘Can we lose almost everything … and just pretend she got up and had very little to say and [for] once is speechless?'”

Wilde nervously seeked Silberman’s approval, “I looked at Katie, thinking she’d say, ‘Are you kidding me, do you know how long I spent on these speeches?’ And she was like, ‘It works, take it all out.’ And I was so grateful for that kind of collaborative energy, it’s rare.”

A Secret Short

Wilde shared a few details about another project she’s been working on somewhat in secrecy: a short film shot in New York City by cinematographer Matthew Libatique and starring “Once Upon a Time in Hollywood” breakout Margaret Qualley.

“It was a chance for all of us to play and it could be really cool, and it could end up, I don’t know, being seen by no one or everyone,” said Wilde. “It was for me a real wish fulfillment experience because I had worked with Matty as an actor, and to be able to direct with him was so fun.”

Wilde is basically done with the short, having finished the sound mix last month. The film is at least in part inspired by the Perfume Genius song, “Otherside.” “I used [the song] as my inspiration for my short in how I would write it,” said Wilde. “I heard the song, I thought about the emotional beats and I was like, ‘I’m going to write the emotional beats of this song.'”

Asked if there was an outlet or distributor attached to the short, Wilde was coy, “Maybe.”

The Filmmaker Toolkit podcast is available on Apple Podcasts, Spotify, OvercastStitcherSoundCloud, and Google Play MusicThe music used in this podcast is from the “Marina Abramovic: The Artist Is Present” score, courtesy of composer Nathan Halpern.

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