Olivia Wilde on her directorial debut, the #MeToo era and the importance of female alliances

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11th Jul 2019

n a spring day last year, Olivia Wilde met two young actresses, Beanie Feldstein and Kaitlyn Dever, for lunch at a restaurant in Los Angeles. Wilde had cast the pair as co-stars in Booksmart, her upcoming film that would mark her transition from actor to director, but Feldstein and Dever hadn’t even met. Before the appetisers arrived, Wilde got straight to the point: “Wouldn’t it be incredible if you could live together?” she asked them. Feldstein remembers it like this: “Kaitlyn and I, having known each other for 20 minutes, just looked at one another. We were like: ‘Can we do that?’”

Wilde explained to them both how the film was centred around the unique bond between two best friends on the cusp of graduating high school, Molly, played by Feldstein, and Amy, played by Dever, and how she wanted their relationship to feel authentic. “In order for it to work, we had to be those girls and feel that friendship and then have it sort of emanate from us,” says 26-year-old Feldstein, who at the end of the lunch agreed to share a room with her co-star for a month before production started. “By the time we started filming we knew almost all our lines,” Feldstein says. “We knew the other person so well that by the time we got to set we were able to play around and be free in those scenes.”

It was a shrewd move for a debut director but, as Wilde explains, she approached the entire project with this kind of meticulousness. “I spent the better part of the last two years only working on, thinking about and believing in Booksmart. I wanted to give it my all, because I didn’t know if I’d ever be allowed this opportunity again.”

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Born in New York, Wilde has acted in more than 30 films, including Oscar-winning drama Her and the Golden Globe-nominated Rush, and starred in television’s The O.C. and House. Her most recent film, A Vigilante, in which she plays an avenger helping victims escape their domestic abusers, afforded her critical acclaim when it debuted at the South by Southwest festival last year. Wilde has also played the role of producer, including for the drama Meadowland, in which she also starred. She says these experiences inched her closer to the director’s chair. “I made the switch now because I finally gained the courage to do it,” she says. “I’ve been wanting to direct now for over 10 years. I started with a short film, and then I made a couple of music videos, and what those experiences taught me is that I am my happiest on set as a director. It let me know that I had to make the leap.”

Wilde is part of a crop of young female directors rising up with the force of the #MeToo and Time’s Up movements behind them. The 35-year-old credits both for making space for her behind the camera – all four of Booksmart’s writers are women and out of five producers, four of them are female. “I think what the #MeToo movement has done is create an alliance between women in this industry who had been kept previously isolated from one another,” Wilde explains. “There was a sense of competition that was encouraged by, I think, the male leadership within the industry, because it is very convenient to keep women competing with each other. Once we link arms and actually collaborate on something, we’re incredibly powerful.”

This show of female unity ultimately gave Wilde the confidence to direct her first feature, but it has also informed the kind of films she wants to make. “[It] really inspired me to create content that contributed to that conversation and reminded people of the strength in female alliances. So telling a story about female friendship was my way of bringing attention to the incredible power of a friendship that is the link between women.”

In Booksmart, Amy and Molly are two ride-or-die best friends and academic overachievers who thought they had to choose studying over partying, only to discover their peers did both and still got into Ivy League colleges. On the eve of their graduation the pair attempts to make up for lost time with one unforgettable night. The storyline has drawn comparisons somewhere between Superbad and Bridesmaids, but in reality it’s a unique and fast-paced coming-of-age story and Wilde says she was more inspired by action films like Beverly Hills Cop and Lethal Weapon.

“I wanted to tell a story about dynamic, complex, nuanced women,” says Wilde. “There’s a challenge in being a woman in that we feel we have to be kind of everything at once. We want to be both professional and maternal; we want to be both nurturing and really independent and powerful. All of these qualities feel somehow essential in proving that we are as valuable as men, who don’t worry about proving their multidimensionality as much at all. That’s kind of been true for so many women and it’s a burden to carry.”

Of the two main characters out to prove their complexity the most is Molly, who Wilde cast with Los Angeles-born Feldstein, a rising talent. She joined the cast off the back of fellow coming-of-age film Lady Bird, which she starred in alongside Saoirse Ronan, and she’s also had a stint on Broadway in Hello, Dolly! next to Bette Midler. (Her brother is actor and director Jonah Hill.) Feldstein calls Molly a “wrecking ball”, but agrees the real hero of the film is the relationship between the two girls.

“It’s a friendship that is created over an intense celebration of one another and an adoration of one another and I’ve never seen that on screen,” adds Feldstein, whose next project is the adaptation of Caitlin Moran’s semi-autobiographical novel How To Build A Girl. “These stories are now finally being directed by the women that they’re about. I’ve done five films, and four of them have been directed by women, which I think is a pretty remarkable thing. Something is shifting, but you also have to be a part of that shift. Olivia always says to us: ‘You have to change the paradigm from within.’ It’s a phrase that I just think about once a day.”

Since that first fateful lunch meeting, Feldstein and Dever, 22, now share a special bond with their boss. On a recent Instagram post from Booksmart’s London premiere, Wilde captioned a shot of the three of them with the caption “Find someone who adores you the way I do these two.” Feldstein similarly calls them a “girl gang for life”.

“Liv was saying yesterday that we’re truly bonded forever with this movie, and she couldn’t feel more lucky. Kaitlyn and I were sitting there tearing up,” says Feldstein. “Olivia was an intensely collaborative, energetic, brilliant and warm force on set. Molly was a really intimidating character for me to play, I was really nervous [but] because we had done so many rehearsals and we’d had so many talks, I felt so prepared. I felt safe in her hands.”

For the cast it felt like family on set, but for Wilde it actually was. She chose to cast her real-life partner, comedian and actor Jason Sudeikis, 43, in the film as the high school principal. The couple has been together since 2011 and also share two children – Otis, five, and Daisy, two.

“Jason is one of the best improvisers on Earth, and when I met him, I had been a fan of his already for a number of years from watching Saturday Night Live,” says Wilde. “I continue to be amazed by his skill and the way he can turn a bit of material into something much, much bigger and more hilarious. I was standing behind the monitor just blown away by what he can do, and watching his scenes are some of my favourite moments in the film.”

Although Wilde now feels comfortable behind the monitor, she says it’s not necessarily where she’ll remain. “I don’t think it’s a switch. The cool thing about this industry is we can maintain different roles. I’ve been producing movies for years while acting, so I’m hoping that I can produce, act and now direct. I think so often we stand in our own way, and the first ‘yes’ that we really need is from ourselves,” says Wilde. “I finally gave myself that ‘yes’.”

Booksmart is in cinemas from July 11.

This article originally appeared in Vogue Australia’s July 2019 issue.