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A Conversation with Olivia Wilde, Beanie Feldstein, and Kaitlyn Dever of ‘Booksmart’ at the Brattle Theatre

‘Booksmart’ feature still
Director Olivia Wilde (left) and actor Kaitlyn Dever (right) on the set of “Booksmart” (2019).

Olivia Wilde, known for her roles on “House” and “Tron: Legacy,” made her feature film directorial debut with “Booksmart.” The film chronicles the journey of two overachieving best friends who are nearing the end of their high school careers. Molly (Beanie Feldstein) is the typical valedictorian and senior class president who spent her free time in the library, plans to attend Yale, and dreams of becoming the youngest Supreme Court Justice. On the last day of school, she confronts her slacker classmates on what colleges they’re attending and realizes that the slogan “work hard, play hard,” actually applies to her classmates, who managed to get into elite universities while still enjoying a social life in high school. This discovery inspires Molly and Amy (Kaitlyn Dever) to set out on a journey of self-discovery and new adventure. On April 11, after a screening of the film, Wilde sat down with screenwriter Katherine Silberman, Dever, and Feldstein at the Brattle Theatre to field questions from the audience.

Silberman was the first to be attached to the “Booksmart” script after it remained on Blacklist — an annual survey of Hollywood’s favorite unproduced screenplays — for about 10 years prior to its production. She explained her reasoning behind getting involved with the film and what she found particularly special about it. “A new entry into the high school comedy canon and to tell a story about a real authentic female friendship in 2019, and what that means for this generation of young women,” she said.

Feldstein commented on her track record for female-led movies and on how “Booksmart” set the bar even higher for her. She said, “My previous projects such as ‘Lady Bird,’ set the bar extremely high for me in terms of working on films with other directors.” “Olivia was the best person for the job in terms of mentoring and hiring women for the job and I’ve been lucky to work with an amazing slate of female directors,” she said. “Olivia created a communicative and inclusive environment, which has given me an interest in directing.”

Dever also felt similarly about Wilde, who she saw as her role model. “I would often text Olivia and be like, ‘I was just listening to a song and had an idea for a music video’ and Olivia would encourage me to be brave and bold and tell me to go for it and direct one,” she said.

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“Booksmart” wasn’t Wilde’s first directing project. In the past, she has directed shorts and music videos which helped influence how she directed the set. Noting that the film industry has been historically male-dominated, Wilde set out to change that narrative. “No matter what industry you’re in, whether it be directing or finance, you have the power to do that," Wilde said. "I wanted to do everything differently in whatever capacity available. Being in the driver’s seat allowed me to pair so many brilliant people in a way that was conducive to produce their best work.”

Wilde stated that one of her biggest influences as a fledgling director was her close friend Reed Morano, who is a cinematographer and director known for her work on “Kill Your Darlings” and “The Handmaid’s Tale.” Besides providing Wilde with the technical knowledge of how to direct and run a film crew, Reed also taught her to develop the courage to pitch on “Booksmart.” Wilde also mentioned her experiences with past directors such as Martin Scorsese, who taught her important lessons that she implemented on her set. “Scorsese has a no-script rule which I stole for my set since we only had 26 days to shoot the entire film and having the no-script rule meant that everyone had to be on top of their game and thankfully everyone was," Wilde said, adding “He also has a no-phone rule, but since we are a fairly young cast, I didn’t steal that rule.”

Wilde also explained how she managed to facilitate strong on-screen chemistry despite her tight production schedule. She said, “Something magical when we started shooting was that everyone gravitated towards each other, no one went to hang out in their trailers alone. It became like camp very very quickly and this informed the connections which made friendships that went deep.”

In an effort to foster organic friendships among the cast, Wilde sent them out on adventures in order to strengthen their connections. She said, “I wanted them to feel like old friends so I would send them on adventures together saying, ‘You need to go to the mall, go to the movies, have a wild night out, hang out at someone’s house,’ and they would send me pictures as proof, all of which contributed to the genuine interactions seen throughout the film.”

Dever and Feldstein spoke to the benefit of already going through high school before portraying teenagers as adults.

“I was 20 or 21 when we shot Booksmart, which is a few years after I graduated which allowed me to reflect on my time at high school,” Dever said.

Feldstein even visited her former high school before shooting, which got her excited for shooting the film. “Meeting the kids, I was so inspired since they’re all so smart and they knew words that I didn’t even know,” she said.

Wilde made sure to emphasize that she meant to naturally highlight the complexity of the teenage characters without sensationalizing any of their identities. The script mentioned that Amy’s character would be gay and it was something that Wilde treated in a way where it didn't affect the narrative. “It [her sexuality] didn’t make a difference — it might as well have said, ‘She has brown hair,’ since we wanted to make it as authentic and fluid as possible. ‘Booksmart’ portrayed Amy’s self discovery in a way that all adolescents experience it rather than isolating her experiences as something foreign,” she said.

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