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Olivia Wilde: Learning to Be Herself

By Dave Itzkoff

“It only gets more interesting when you’re too old to play dumb,” said the actress-turned-filmmaker.
Ryan Pfluger
“It only gets more interesting when you’re too old to play dumb,” said the actress-turned-filmmaker.

Before Olivia Wilde was a first-time feature director or the star of innumerable projects that she was told would make her the Next Big Thing, she was one more Hollywood newcomer looking for guidance. It was in this unsettled period when Wilde, then around 20, spotted Tilda Swinton at a Golden Globes party, sidled up to her ethereal, chameleonic heroine and awkwardly asked for advice.

If Wilde expected Hollywood to be an “All About Eve”-style combat zone where ingénues were worshiped and maturity was something to be feared, Swinton’s counsel threw her for a loop. She told Wilde that with age came self-assuredness and clarity about one’s identity. In her own work, Swinton said to her, “I can just be very specifically me.”

It’s an encounter that Wilde has been reflecting on for the last decade and a half, but its lesson, as she interprets it, is one she has come to understand only recently.

Forget the myth that actors have to cherish being young and will never know a better time in their lives or careers. As Wilde told me a few weeks ago, “It only gets more interesting when you’re too old to play dumb.”

Wilde has a résumé that is rife with simmering, sexualised supporting roles on TV melodramas (“The O.C.,” “House,” “Vinyl”) and in not-quite-blockbuster movies (“Tron: Legacy,” “Cowboys & Aliens”) — often reflections of how others saw her rather than how she saw herself. But if she once believed it was her responsibility to embody “everyone’s version of a perfect woman,” she said she had learned, “I don’t have to carry that.”

Her new movie, “Booksmart,” would be special enough to her because it is her directorial debut, but Wilde said it held further value. “It is remarkable that I am 35 years old and this is the first job I’ve ever had that wasn’t entirely dependent on and connected to my looks,” she said. “It grosses me out to acknowledge it, but I’ve been thinking a lot about it.”

“Booksmart,” at a quick glance, might not seem like the kind of film that would stir up defiant feelings. The movie, which opens May 24, is a bawdy, unapologetically raucous comedy about two studious friends (played by Beanie Feldstein and Kaitlyn Dever) trying to make the most of the last night before high school graduation.

Where many actors-turned-directors make debut movies that are eye-rollingly political or pretentious, “Booksmart” would love to be a latter-day “Dazed and Confused” or “Ferris Bueller’s Day Off” — a celebration of adolescence, from a decidedly female perspective. It is also, pointedly, a story about not evaluating people on their appearances.

The movie was received enthusiastically when it made its debut at South By Southwest in March. Variety wrote in its review, “Not since ‘Superbad’ has a high school comedy so perfectly nailed how exhilarating it feels to act out at that age,” adding, “In this year’s class of first-time feature directors, Wilde handily earns the title of Most Likely to Succeed.”

Like her “Booksmart” characters, Wilde is enjoying her own newfound freedom; she is realising that “Booksmart” might finally be the movie that provides the filmmaking experience she’s always wanted.

She isn’t bidding farewell to her acting career nor disavowing her past work, though she sees some of it in a new light. “Was it ever truly purely me,” she asked herself, “or was it always something that was fraught with a sense of superficiality, of being judged from the outside in an external way? I don’t know.”

But with “Booksmart,” she said: “I was there only because of my brain and my heart. And the sense of fulfilment that comes from that is really massive. It’s a profound shift for me.”

On an April afternoon, Wilde was having lunch at a Brooklyn restaurant near the home she shares with her fiancé, Jason Sudeikis, the “Saturday Night Live” alum, and their children, Otis, 5, and Daisy, 2. The biggest dilemma facing her that day was whether to bring Otis with her to a Beastie Boys stage show that night.

Ryan Pfluger

She spoke self-deprecatingly about her home life, describing herself and Sudeikis as people who “tend to build the parachute on the way out of the plane.” The day Otis was born, she said, was “the most clichéd New Yorker moment of my life — I was in the hospital bed, texting my Realtor, ‘I’m ready, give me Brooklyn, I want wide-open spaces.’”

Wilde, who chose her stage name as a homage to Oscar Wilde, grew up in a high-achieving household. She is the younger daughter of Andrew and Leslie Cockburn, the journalists, documentarians and socialites whose book “One Point Safe” was the basis for the 1997 thriller “The Peacemaker.” (Christopher Hitchens, a family friend, wrote that when Olivia was younger, he served as the “occasional supervisor of bedtime stories and suitable viewing fare” for her and her siblings.)

As a teenager, Wilde attended Phillips Academy, the elite boarding school in Andover, Mass., and she was fascinated by the seemingly carefree, liberated teenagers she saw in films like “Clueless” and “Fast Times at Ridgemont High.”

When she started acting, Wilde was quickly absorbed into Hollywood’s bloodstream in the early 2000s: first, on the short-lived Fox drama “Skin,” playing the daughter of a pornography mogul, then on “The O.C.,” as a bisexual bad girl who dated the show’s male and female leads. You could wave those roles off as cookie-cutter, eye candy, but Wilde sees them as important steppingstones.

“I used to dismiss ‘The O.C.,’” she said. “I’d be like, ‘I did a teen soap — what an embarrassment.’ And now I think, ah, that was really formative and I’m lucky I got to do that.”

She is sanguine, too, about the string of misbegotten movie roles she was assured would propel her to a higher tier of stardom. Before the 2010 release of “Tron: Legacy,” the sci-fi adventure that cast her as a cat-suited digital warrior, Wilde said, “everybody was like, ‘Are you ready for this?’”

“I had security experts saying I was going to have to put protective steel shields on my windows,” she added. “And of course that didn’t happen.”

It didn’t happen, either, with “Cowboys & Aliens,” which just happened to see her emerge naked from a funeral pyre, or “Rush” or “The Incredible Burt Wonderstone,” or “Vinyl,” a one-season HBO dud in which Wilde played a former model-actress whose character arc again somehow called for nude scenes.

When she looked back on these projects, Wilde was upbeat rather than heartbroken. “I somehow developed a solid core of confidence that has allowed me to weather the storms of almost everything not working out,” she said. She likened the experiences to dating, adding: “None of this is commitment. This is me learning, and then realising, I know what I want to do with it.”

Yet, without quite pointing to specific instances or past collaborators, Wilde said she had faced enough examples of being categorised for her looks — and the expectation that she can play only certain types of sexualised or available characters because of them — that it had caused her to question her talents and accomplishments.

“Have I ever felt exploited?” she said, a tone of resignation slipping into her voice for the first time in the conversation. “Yeah. Do I realise that I’d become numb to that? Yes. I had become numb to the fact that every meeting I went on — with men and women, by the way — I was going to be judged on my physical appearance. Because that’s what actors deal with, and man, it’s exhausting.”

In recent years, Wilde has been building a portfolio as a director — an area, she said, where “my value had nothing to do with my looks” — making music videos for the Red Hot Chilli Peppers and Edward Sharpe & the Magnetic Zeros, and a short film for Glamour magazine. She produced documentaries as well as fictional features in which she also starred, like the Joe Swanberg comedy “Drinking Buddies.”

Spike Jonze, who cast Wilde in a small role in his 2013 techno-romance “Her,” remembered her for an innate curiosity that is fundamental to filmmaking.

Ryan PflugerWilde on being a woman in Hollywood: “Have I ever felt exploited? Yeah. Do I realise that I’d become numb to that? Yes.”
Wilde on being a woman in Hollywood: “Have I ever felt exploited? Yeah. Do I realise that I’d become numb to that? Yes.”

“She’s very unprecious,” Jonze said. “She came in with no insecurity or ego to deal with. It was just, O.K., what do you want me to do? She’s driven, really, by an excitement to make things and to learn, and to try things she doesn’t know how to do.”

Jonze has since become a friend and an occasional sounding board when Wilde seeks advice on directing. “It’s fun to talk to her about it,” he said, “being around somebody who’s totally passionate and turned on, wanting to learn and grow and try things, push herself.”

“But,” he added, “you don’t know if you’re a filmmaker until you do it. It’s a trial by fire.”

Wilde also made a lasting impression on Jessica Elbaum, the president of Gloria Sanchez Productions, when they produced a Comedy Central TV project together.

Elbaum was also helping produce “Booksmart,” which had been acquired by Annapurna Pictures, the independent studio behind “Vice” and “If Beale Street Could Talk.” The original “Booksmart” screenplay, by Emily Halpern and Sarah Haskins, had received a rewrite from Susanna Fogel, but the project had stalled and needed fresh eyes.

Elbaum, whose company focuses on female-led films, encouraged Wilde to pitch herself as the film’s director. “I just had this feeling, not really based on anything other than my gut,” Elbaum said.

Wilde read the script and said she felt an affinity for it, believing she could turn “Booksmart” into “a generational anthem — something that would help people find the joy and fun of growing up.”

She added: “To be young must be so hard right now. They cannot just focus on being young.”

In her proposal to Annapurna executives, Wilde framed “Booksmart” as “the ‘Training Day’ of high school comedies,” meaning a story with high stakes for its main characters. “Could there be anything more terrifying than feeling like your entire existence is resting upon academic success and social standing?” she said. “At the time, it feels like life and death.”

That approach connected with Megan Ellison, the Annapurna founder, and its president of film then, Chelsea Barnard, who gave Wilde the assignment. (Barnard has since left the studio.)

Ellison said in an email that Wilde’s perspective “immediately resonated with me and I knew the story was hers to tell.” She added, “High school coming-of-age movies have been done so many times, so it didn’t feel worth it to us to make the film unless it felt authentic, exciting and fresh.”

Elbaum, the Gloria Sanchez president, said that having female gatekeepers in decision-making positions was “a million percent” responsible for Wilde landing the job. “It was all female-led and women wanting to support women and be there for women,” she said. “I really do think that made all the difference.”

Wilde then hired the screenwriter Katie Silberman to make further revisions, add characters and underscore the theme that as much as the lead characters want to be seen for who they are, they must also set aside their prejudices about the classmates they reject out of hand.

“This is not a movie about two nerdy girls trying to assimilate,” Wilde said. “It’s about them learning to accept others.”

Silberman said that Wilde had clear and specific ideas for scenes she wanted to add — say, an accidental drug trip that the two heroines share — and the trajectory she wanted her characters to follow.

Ryan Pfluger

“We could tell a story about smart women where their intelligence was the baseline, and then they got to be characters on top of that,” Silberman said. “They have very clearly chosen school over fun, and then realised they were the only ones who made that choice.”

After starring in a series of demanding, depleting roles — the mother of a missing child in the drama “Meadowland,” a vengeful defender of abuse victims in the thriller “A Vigilante” and the dissident Julia in a Broadway adaptation of “1984” — Wilde was ready for the escapism of “Booksmart.”

The film was shot in just 26 days last year, requiring Wilde to draw on the moviemaking strategies she had learned from her past directors. (Taking a cue from Martin Scorsese on “Vinyl,” she required her actors to have all their lines memorised before they arrived on set.)

“Booksmart” also afforded opportunities for Wilde to right the wrongs she experienced on other projects and run the kind of protective, nurturing film set she’d always wanted

When it came time to film an intimate love scene between Dever and another actor, Wilde said: “I was so excited to explain to everyone what I thought a closed set should mean. There aren’t 100 people in the room. I can’t tell you how many times I’ve done a love scene where I’ve been like, ‘But surely that guy doesn’t need to be there?’”

Dever, a star of TV’s “Last Man Standing” and “Justified,” said she fully trusted Wilde, as a director and as an arbiter of a youth culture she outgrew some time ago.

“She’s so wise,” Dever said. “She’s been here before — many times, I think. There was never a moment where I doubted anything that Olivia was doing.”

Feldstein, who played a supporting role in “Lady Bird,” compared Wilde to that film’s writer-director, Greta Gerwig, who was also an actor making her solo directorial debut with a comedic coming-of-age story.

“You just know when someone’s meant to tell a story, and when you’re part of something that is meant to be told,” Feldstein said. “On ‘Lady Bird,’ I felt I was seeing someone create something that only they could tell. And then when I met Olivia, I was like, ‘There’s two of them?’”

A directorial follow-up seems all but certain for Wilde, though neither she nor her “Booksmart” partners have found it yet. Whether it’s another comedy, a drama or something else entirely, Elbaum said: “I’m desperately trying to find it. I literally send her everything that comes across my desk.”

Wilde said she remained committed to acting, even more so now that she’s been on the other side of the camera. “Acting is catharsis,” she said. “It’s therapy. It only gets better when you’re not doing it out of necessity.”

For now, Wilde is savouring the “Booksmart” experience and feeling like she has finally lived up to the potential that others saw in her. Recalling another formative celebrity encounter, she talked about meeting Steven Spielberg at an event for “The Peacemaker” and telling him she also wanted to make movies.

Some time later, Wilde received a note from Spielberg that read: “If you wanna be a doctor, look before you leap. If you wanna be in show business, leap before you look.”

Wilde had the note framed and keeps it in her office. “I want to tell him I took that leap,” she said.