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Even Olivia Wilde Gets Imposter Syndrome
Photography by THOMAS SLACK
Even Olivia Wilde Gets Imposter Syndrome
Photography by THOMAS SLACK
The actor and activist is on a mission to change the face of sisterhood in Hollywood

To say that Olivia Wilde is not your average A-lister is an understatement. Alongside her work as an actor, model, producer and activist, passionately campaigning for women’s rights and lending her support to the Planned Parenthood and Time’s Up movements, Wilde recently added director to her evergrowing list of accomplishments. Today, she is one of just a handful of women to make the move from in front of the camera (you’ll recognise her from leading roles in films like Tron: Legacy and Rush, as well as the TV series House) to behind it. Her first feature-length film, Booksmart, hit cinemas last summer to rave reviews, landing Wilde Breakthrough Filmmaker of the Year at the CinemaCon Awards. And as with every important choice in her life, this decision was one born out of a fundamental desire for change.

“I realised I had spent more than half my life on set and was starting to become frustrated that I didn’t have creative control over the projects I was working so hard on,” says Wilde over the phone from Los Angeles. “So I decided it was time to step up. I’m a firm believer that you can’t complain about anything unless you’re willing to do it yourself.” The result is a whip-smart coming-of-age comedy about two female best friends (played by rising stars Beanie Feldstein and Kaitlyn Dever), in the tradition of the great teen movies that Wilde devoured while growing up. “When I think about my adolescence, I think about watching and rewatching films like The Breakfast Club, Dazed and Confused and Clueless,” says Wilde. “These were movies that helped me contextualise the experience of growing up. It’s easy to discount those films as superficial, but they are significant in the messages they send to young people. And I don’t take it lightly, that responsibility to communicate to young people at a time in life that can be very confusing.”

"I’m a firm believer that you can’t complain about anything unless you’re willing to do it yourself"

Wilde’s own teenage years were ones of bohemian liberalism. Born Olivia Jane Cockburn – she changed her surname to Wilde in high school in homage to literary hero Oscar – she was raised in the affluent Washington, DC neighbourhood of Georgetown in a family of journalists. Her London-born father, Andrew, has written for the likes of Vanity Fair and The New York Times, while her mother, Leslie, is an investigative journalist and filmmaker. Both her uncles were journalists, as was her grandfather, and it wasn’t unusual for literary heavyweights such as Salman Rushdie or Christopher Hitchens to pop over to the family home for dinner.

She eschewed the traditional path of drama school and, aged 19, eloped with an Italian Prince, Tao Ruspoli – the couple got engaged at Burning Man and were married on a school bus with only two witnesses. In the past she has described their marriage as "unconventional" and they divorced when Wilde was 27, a time she has cited as a significant period of change. “I started taking things more seriously when I was 27, which I think is when a lot of women begin to step into leadership positions,” she says. “That’s when I started making a short film and music videos, and found that I was so much happier in the role of the director.” Wilde says the second significant period in her life came last year, while she was making Booksmart. “I directed the film when I was 34, and I do think for women there are these markers in their lives – 27 and then 35 and beyond. For me, there’s been a significant shift at those ages, and I think that’s connected to a sense of confidence that comes from maturity.”

Actor, model & activist Olivia Wilde. Photography by Thomas Slack

When Wilde discusses her experience of directing, the joy it elicits in her is palpable, but she admits she still suffered from a classic case of imposter syndrome before starting the project. “I do think what was holding me back for a long time is what holds a lot of people back," she says. “I thought, ‘I’m not qualified, I don’t know enough.’ And then I thought, ‘Wait a minute – I’ve spent so much time on sets, I have shadowed so many great directors, surely I’ve gained enough knowledge.'" While she confesses that the experience was gruelling – the entire film was shot in just 26 days with a young and largely inexperienced cast, two of whom had never been on a set before – she says she found it profoundly energising. “Even though it was exhausting, I was electrified by it. When I reflect on it now, it’s kind of incredible that all I remember is the thrill of it and the deep sense of happiness and gratitude. But somehow, all of the positive emotions have eclipsed any of the stress.”

She attributes that largely to the team she assembled, in particular her youthful cast. “I was really moved by Beanie and Kaitlyn and how willingly they threw themselves into this process and committed so completely,’ she says. “As actors get older, it becomes about, ‘Alright, I have a family, I can’t commit all my time to this.’ Or ‘I have several projects’, or ‘I own a company’, or ‘I’m afraid to give too much of myself, because I’m managing my image.’ Young people at the beginning of their careers are so vulnerable and fearless. I found that really inspiring.”

Olivia Wilde poses for Allbright magazine. Photography by Thomas Slack

Alongside charting the trials and tribulations of transitioning from adolescence to adulthood, the film also explores the complexities of female friendship, another theme close to Wilde’s heart. It’s something she was hell-bent on getting right on screen, to the point where she asked the two main characters to live together for a month before filming started, because she knew “the texture of that long friendship is a really hard thing to fake. It’s a multi-layered type of chemistry.” 

When I ask how important female friendships have been in her own life, she suddenly turns serious. “Female friendships are sacred to me. They have gotten me through the most difficult times in my life and I am deeply committed to them. I think that as you get older, you realise the profundity of that connection, of having a chosen sister. It is extraordinary to feel that type of love and trust and vulnerability.” She starts to lament how much society overvalues romantic relationships before catching herself and clarifying, with a laugh, “That’s not to say that I don’t value romantic love, because I do and it’s wonderful!” (Wilde is engaged to the actor and comedian Jason Sudeikis, and they have two children, Otis and Daisy, who both cameoed in Booksmart.) "But I do think there’s something about the chosen family of sisterhood, of female friendship, that is really remarkable. It’s important to connect to someone who understands you on a different level to a romantic partner.’

"I do think there’s something about the chosen family of sisterhood, of female friendship, that is really remarkable"

The notion of sisterhood has become even more important in a post-Weinstein Hollywood, and Wilde has been a vocal supporter of the Time’s Up movement and the welcome changes it has brought to the industry. “Time’s Up has been a total shift for this business and for me personally,” she says. “Historically, actresses were kept apart and there’s this narrative perpetuated by men that we don’t like each other, and yet it couldn’t be further from the truth. There’s been this shift in terms of women coming together in a non-competitive manner and understanding our value and our power when shared." She says this change in attitude has allowed her to connect with other high-profile women who are going through similar challenges, something she has found incredibly comforting. “I remember when I was starting to put Booksmart together and I saw Brie Larson at a Time’s Up meeting. She just held me and reassured me and told me that I could call her at any moment. And then she checked in throughout the process of the film. This is someone who Hollywood – or, rather, the myth of Hollywood – would assume is a competitor.” 

Another myth Wilde struggles with is perpetuated by the vast majority of the American beauty industry, who claim to be helping you become the best version of yourself while including carcinogenic and poisonous ingredients in their products. “Beauty is a tricky thing – it’s very interesting to me that we all willingly sacrifice our health in the name of perfection," she says. “For me, clean beauty is a political act. Once I started learning more about the harsh ingredients in our products, and our children’s products, it became necessary for me to seek out the companies that are doing things differently.” One such company is natural and organic skincare brand True Botanicals, for whom Wilde is the chief brand activist. "It’s wonderful to be a part of their movement, because they’re trying to change the way the industry actually works, not just trying to achieve success themselves. With my platform I want to help educate people about opportunities for finding alternatives to this truly gross and poisonous stuff that’s out there.”

She believes the beauty industry still has a long way to go in terms of diversity, but is encouraged by signs that things are moving in the right direction. “It brings me great joy to see women of all races – and men, of course – being celebrated for their beauty. I think it’s really interesting how Instagram has democratised the process of advertising. Now consumers are choosing their beauty icons rather than waiting for a corporate entity to tell them who to aspire to be. That’s very exciting to me.”

So other than lighting a fire under the film world and taking on the multi-billion-dollar beauty industry, what’s next on Wilde’s agenda? “I’m still figuring that out," she says. “Booksmart was my entire life for two years and now that I know the sacrifice that’s necessary, I’m being very careful about what I throw myself into. This is a reality for female directors with children. It bothers me that there has always been this brotherhood of men in this industry. You think of the great directors of the 1970s – Scorsese, De Palma, Spielberg, Coppola – and how they had each other’s backs. And I really want that to exist for women. There’s no reason why we shouldn’t have that same sort of structure and collaborative energy.” She pauses. “But I am excited, because I do find there are more opportunities for female directors right now. And who knows how long that will last? I’m going to grab hold of it and make as many interesting things as I can.”

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