Olivia Wilde Is Living Her Best Life (2024)

But even as Wilde demonstrated, early in her career, that she could carry prime-time TV and big-budget Hollywood projects, she proved herself as an actor who excelled at teasing out the complexities of more nuanced roles: as a grieving mother in Reed Morano’s Meadowland, or as a just-one-of-the-guys girl whose breezy swagger hides a bruised heart in mumblecore king Joe Swanberg’s Drinking Buddies.

Then, in 2019, Wilde released her first feature, Booksmart, and re­invented herself as something else entirely: a filmmaker. “I’ll never forget the moment at South by Southwest when we premiered it, and I was shaking backstage thinking, I’ve never felt more exposed,” Wilde tells me. “Then people started coming up to me saying that they loved it. The relief was incredible.” She goes on, “You know, Tarantino always says, ‘Make the movie only you can make.’ So I knew that with my first opportunity, I had to make something that just had my DNA all over it.”

The film follows two best friends, played by Beanie Feldstein and Kaitlyn Dever, as they try to make amends, on the last day of high school, for having spent the past four years studying while snobbishly judging the exploits of their more libertine classmates. Over the course of a nightlong quest to reach a house party, they will watch lesbian p*rn (for educational purposes, naturally), impersonate armed muggers, and get so stoned on strawberries spiked with a mysterious substance that, in a memorable two-minute stop-motion sequence that took a Portland animation studio four months to produce, they turn into Barbie dolls.

Booksmart said something real and relatable about how it feels to be a modern young woman who is confident, intelligent, motivated, and yet, as an earlier classic put it, clueless. The movie was a critical success and earned an ardent fan base, though, Wilde confesses, “it didn’t make any money.” It failed to clear the hundred-​million-dollar mark, she says, and “it’s much harder for female directors to get a second film greenlit if your first one didn’t make $100 million.” Nevertheless, when Wilde and Katie Silberman, her producing partner, shopped Don’t Worry Darling around to studios, an 18-way bidding war erupted. “Booksmart hit a cultural artery,” Wilde says. “Even the studios were able to look beyond the financial success. There’s so much content now. Hitting a nerve is muchharder.”

Wilde has known that she wanted to direct for almost as long as she’s wanted to act, and she’s known that she wanted to act for a long time. She grew up in Washington, D.C., the second of investigative journalists Andrew and Leslie co*ckburn’s three children. (Wilde changed her last name as an 18-year-old theater student in Dublin, in homage to Oscar.) Along with his brothers, Alexander and Patrick, Wilde’s father, who was born in England and raised in Ireland, is a member of an impressive journalistic dynasty. Wilde’s extended family tree includes: her grandfather Claud co*ckburn, a prominent English communist who founded the radical magazine The Week; the baronet who ordered the 1814 Burning of Washington; and Evelyn Waugh. She was particularly close to her uncle Alex, who died of cancer in 2012; she named Daisy after his daughter. (“Losing him was the hardest thing I’ve gone through as an adult,” she confides. “And I’ve gone through some sh*t.”) When she was little, Wilde liked to hide out under the dining room table during her parents’ raucous dinner parties, eavesdropping on the heady adult conversation. Christopher Hitchens was prevailed upon to babysit: “I’m sure it’s in my bloodstream still,” she says, of Hitch’s omnipresent cigarette smoke.

But the family business never tempted Wilde. “I’m aware of how thankless the job of a journalist is,” she says. Her parents were untroubled by her defection. As a young woman, Leslie had elbowed her way into the old boys’ club of TV news, covering the Khmer Rouge, the Russian mafia, and the Taliban’s takeover of Afghanistan, among other high-profile, high-adrenaline subjects, and she respected her daughter’s need to forge her own path. “She just took me so seriously when I said I loved something or wanted something,” Wilde remembers. “She didn’t dismiss it as childish. Like being an actor. I mean, so many parents would be like, ‘Okay, that’s nice, but we’re going to make sure you get a degree in something real.’ ”

And Wilde is happy: radiantly, rapturously so. She tactfully avoids naming Styles as the source of her newfound joy (nor would her representative confirm the relationship). But ample evidence of the couple canoodling, and of Wilde bopping along in the audience at Styles’s shows—a supporting role of her own, and one that she clearly enjoys—can speak for itself. There’s a playful aspect to her discretion, suggesting not so much a desire to conceal the relationship as to nurture the privacy that love needs to thrive. In any case, it’s not hard to grasp whom she’s referring to when she speaks, glowingly, of the “friend” who accompanied her on a recent trip to her parents’ home, that happened to coincide with Styles’s tour date in D.C., or of the “friend” who gave her the beaded Éliou necklace she is wearing that bears her kids’ names and matches one that Styles is known to sport.

The next morning, I meet Wilde for a private tour of the new Academy Museum of Motion Pictures. She looks elegant and sporty in a long blue-and-white-striped skirt and a navy track jacket by Our Lady of Rocco, her friend and La Ligne designer Molly Howard’s new brand. A tote bag from Styles’s tour dangles proudly from her shoulder.

Olivia Wilde Is Living Her Best Life (2024)

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