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It’s a shining late September morning in Los Angeles and Olivia Wilde is sitting, cross-legged, in front of a bunch of bare butts. Male butts, to be exact: smooth and shapely and dripping with water as the men they belong to emerge from a swimming pool in the black-and-white photograph that is on the wall of her sunny living room. “This is how we want them,” Wilde deadpans from her perch on a mustard-colored velvet sofa.
Wilde, who has spent her nearly two-decade-long acting career as an object of male veneration, knows a thing or two about the rewards, and the risks, of being subjected to a prurient, if admiring, gaze. She can count, among her myriad accomplishments, winning the “hottest Olivia” accolade in Spike TV’s Guys Choice Awards in 2010; lately, she’s been under the public microscope alongside her beau, Harry Styles, who, on the day of my visit, is off trotting the globe for his Love On Tour concerts. This house is a respite from all that scrutiny. When Wilde rented it this past spring, it had already been furnished in a precisely curated, Instagrammable style; we might be in a Design Within Reach catalog. So Wilde can’t take credit for the cheeky art selection or the cheerful, modern decor, or for the sumptuous backyard pool that beckons from every angle of the first floor. Nor, she laughingly assures me, is she responsible for the two unseasonal gingerbread houses displayed on the kitchen counter, which are the handiwork of her kids, Otis, seven, and Daisy, five, whom she shares with her ex-fiancé, Jason Sudeikis.
Wilde has been camped out in Los Angeles since the coronavirus arrived during the week of her 36th birthday. At the time, she was living nearby with Sudeikis and preparing to start shooting her second feature film, Don’t Worry Darling, a psychological thriller starring Florence Pugh and Styles as Alice and Jack, a young couple who join a utopian community in the 1950s California desert. Clearly, it’s been a productive pandemic. A year and a half later, Wilde has emerged with a flourishing new relationship and a nearly finished movie. Just before my visit, the appearance of an 11-second teaser-trailer showing Styles and Pugh making out, Chris Pine screaming in a white tuxedo, Busby Berkeley–style showgirls kaleidoscopically high-kicking, and Pugh trying to rip a cellophane shroud from her face, promptly sent the internet into a fit of ecstatic delirium.
Because of COVID, New Line, which is producing the film, had suggested delaying production until the following year, but Wilde fought to get started as soon as possible; when filming finally began, after a six-month delay, it had to pause twice, each time for a two-week stretch, when someone on set tested positive for COVID. Wilde has no doubt that the extraordinary challenges of shooting under such conditions were worth it. “Every bone in my body knew we had to make it when we did,” she tells me. “I couldn’t be deterred.”
Don’t Worry Darling is slated to be released in September 2022. Wilde has been holed up at home to edit the film, though she finds time to decompress; her TV show of choice has been the HBO Max comedy Hacks. As an East Coast native, she hasn’t totally managed to shake her instinctive skepticism of Los Angeles. “But then this….” She gestures outdoors, letting the pool and the glorious sunshine speak for themselves. “And for kids, it is so much easier. They come home from school and just run out and expend all their energy.”
In a couple of weeks, she’ll head to New York to oversee sound mixing. “I’m always willing to go back,” she tells me. Soon after, Wilde will pick up again, this time for London, where Sudeikis—with whom she shares custody—will shoot the next season of his hit Apple TV+ show, Ted Lasso, and she’ll begin production on her third movie, Perfect, a biopic of the American gymnast Kerri Strug, starring Thomasin McKenzie. Wilde acknowledges that homeschooling during the early months of the pandemic was a strain for Otis and Daisy, but is amazed by their ability to adapt to their shifting circumstances. “It’s wonderful to have them become nomadic in the same way I’ve always been—to feel that whatever country we’re in, they have a routine and a community,” she says. “They’re best friends, and they have each other.”
An avowed optimist, Wilde prefers to focus on what she’s gained in this period of extreme transition, rather than on what she’s lost. Still, so much change can cause confusion. “If you were in my home—” Wilde starts to say, at one point. Then she catches herself: “Where is that? Who knows anymore?” But Wilde has a talent for making herself at home wherever she happens to be. This may not be her beautiful house, but this is very much her beautiful life.
“The woman hasn’t aged,” the cinematographer Matthew Libatique, who shot Don’t Worry Darling, and first worked with Wilde on the 2011 sci-fi Western Cowboys and Aliens, tells me. “She’s eternally youthful.” (For proof, consider a recent unretouched shoot that Wilde did, partly in the nude, for True Botanicals, the beauty and skin-care brand for which she serves as an ambassador.) But I might argue that Wilde—who looks fresh and relaxed in light-wash jeans and a soft peach T-shirt, her nails painted fire-truck red, her feline eyes as piercing as ever—is even more striking now, at 37, than she was at 20, when I, along with the rest of millennial America, first glimpsed her as bisexual bar-owner Alex Kelly on The O.C. That role defined a certain Wilde type: edgy and enigmatic, tough yet feminine, lusted after by men and women alike. (Remy “Thirteen” Hadley, the doctor whom Wilde portrayed for five seasons on House, was also bi—not so much an identity, in the blunt schema of aughts-era mainstream entertainment, but more as a shorthand for a certain reckless, sultry élan.)
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 porn (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 much harder.”
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 Cockburn’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 Cockburn, 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 shit.”) 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.’ ”
Leslie, who ran a spirited, though unsuccessful, campaign for Congress as a Democratic candidate in Virginia in the 2018 midterms, remains a role model for her daughter. “I grew up sitting on the floor of her editing suite, and I saw her in a position of power. I saw her treating her colleagues with respect. I can remember male editing assistants paying attention to her and her voice carrying weight,” Wilde tells me. “I’ve been really lucky to be raised by a woman who has always been fiercely independent and true to herself, and a father who admires her.” She leans forward with a conspiratorial grin. “Oh my gosh, the way my parents gaze at one another! They truly feel the other is the most interesting person in the room.”
Wilde went to boarding school at Phillips Academy in Andover, then decided to defer her matriculation to Bard—and ultimately not to attend—in order to try her luck in L.A. Her parents gave her their blessing. “At every point in my kind of wild adult life, they’ve been so supportive,” Wilde says. “Even when I was 18. I lived on a school bus in Venice. I think about my daughter now, being like, ‘I’m going to move to Venice Beach and live on a bus!’ ” She grimaces.
I point out that Wilde didn’t only live on that bus; she also got married on it, in a secret ceremony to Tao Ruspoli, a filmmaker, photographer, and member of the Italian aristocracy, whom she divorced when the youthful relationship ran its course after eight years.
“I think my parents saw it as eccentric in a way that they sort of both expected and respected,” Wilde muses. “And then it was romantic! They’re both romantics. As long as I was in a safe situation, they were okay.” Wilde is aware of her enormous luck in the parental department. “It’s a safety net, for sure, to know that you can fuck up in a major way, or make a terrible movie, and your parents will still think you’re smart. And probably love the movie!”
As her acting career took off, Wilde began to shadow the directors and cinematographers she worked with, hovering behind the monitor to learn about the differences in lenses and frame rates, film versus digital. “My de facto film school was on set,” she explains.
I suspect that what many women see, when they look at Wilde, is boldness itself. In person, she is an expressive talker, an enthusiastic gesticulator, and an easy laugher. Onscreen, she radiates a self-possession that is untainted by self-seriousness, a quality that she has put to good use in life, too, while campaigning for Barack Obama in 2008, or delivering an address to several hundred thousand protesters at the 2018 Women’s March in L.A. It’s hardly remarkable now for performers to make their liberal politics known. But when Wilde got to Hollywood, Michael Moore had just been booed at the 2003 Oscars for speaking out against the Iraq War; there was, as she puts it, a “shut up and dribble” attitude toward entertainers who spoke their minds. She did so anyway. The woman is not shy.
So it surprises me when she insists that it took her a long time to work up the confidence to try her own hand at directing. When she did finally acknowledge her ambition—she got started with music videos—it was thanks to “a lot of really great mentors daring me to do it.” Then the scrappy Wilde returns as she adds: “And I never turn down a dare.”
I wish I could tell you about the 20-minute selection of scenes from Don’t Worry Darling that Wilde picked for me to watch one morning in an empty office in downtown Manhattan, accompanied by a studio employee whose presence was required to ensure that I was not a bootlegger in disguise. But I’d prefer not to get sued. Instead, let me underline what is already evident from the teaser-trailer: that the movie is ravishing to look at, opulently saturated with impeccable midcentury style and an atmosphere of moody, erotic menace.
“If you can make a comedy that works, you tend to stay in that world, because it can be incredibly lucrative,” Wilde tells me. But she wanted a challenge after Booksmart, which isn’t to say she wasn’t nervous about shifting gears. “Sophomore slump is a real thing,” she admits. She confided her anxiety to Jordan Peele: “ ‘How terrifying was it to make your second film?’ And he said, ‘Oh, so terrifying, so much scarier than the first.’ ”
Wilde describes Don’t Worry Darling as “The Feminine Mystique on acid”—a dramatic departure from the goofy teenage world of Booksmart. Even so, she sees both films as part of an ongoing project to examine female experience from multiple angles. The focus of her first movie, she says, was “friendship and judgment and exploring insecurity.” The new one “is asking the question of, What are you willing to sacrifice in order to do what’s right? If you really think about it, are you willing to blow up the system that serves you?”
The idea for the film crystallized shortly after Trump’s election, when Wilde met Gloria Steinem at “this little gathering in New York City.” Wilde was despondent; she asked Steinem what she could do. Stop paying taxes, Steinem told her. Wilde was aghast. “I said, ‘What?’ I own property. I have kids. I don’t think I can do that.”
Then it hit her: “This is why nothing will change. That was the beginning of Don’t Worry Darling. I was like, Who’s that person who’s actually willing to destroy the structure that is built entirely for their comfort? That’s a selflessness on a level that I admire but admit is far from the way I live my life.”
In Don’t Worry Darling, that person is Pugh’s Alice, a happy young housewife who begins to suspect that all is not well in the glamorous paradise that she and her husband inhabit. Still, the seductions of her world prove difficult to resist. “The 1950s get this rap as a very controlled, conservative era, when in fact it was incredibly debaucherous. My grandparents on my mother’s side loved to party,” Wilde says. One of Wilde’s aesthetic reference points for her film was Poolside Gossip, Slim Aarons’s photo of coiffed women in caftans chatting over cocktails in a Palm Springs backyard whose manicured perfection can’t help but imply some Lynchian rot lurking beneath; another was the thrillers of Adrian Lyne, like Fatal Attraction and Indecent Proposal. Those movies are “really sexy, in a grown-up way,” Wilde tells me. “I kept saying, ‘Why isn’t there any good sex in film anymore?’ ”
About those scenes I watched. Let’s just say that one, featuring a hardworking Styles and a most gratified Pugh, is going to generate some serious attention—and, if the devotion of Styles’s fan base is any indication, hysteria—when Don’t Worry Darling is released. When I work up the blushing courage to ask Wilde about it, she gets technical, talking about overhead angles and wraparound shots, though she readily volunteers that she intends for her audience to “realize how rarely they see female hunger, and specifically this type of female pleasure.”
Wilde had shortlisted Styles to play Jack after admiring his performance in Christopher Nolan’s Dunkirk. But his tour conflicted with the scheduled shoot, and Shia LaBeouf was cast in the role. Then came the pandemic. Live music was canceled; Styles became available, and Wilde, whose team had reportedly clashed with LaBeouf before filming began, brought Styles in to take over. Even before this, the role of Jack had not been easy to fill. Alice is the film’s protagonist; Jack is a supporting part. “I cannot tell you how many men read the script and said, ‘Unless it’s a two-hander, unless I’m in as much—or more—of the script than she is, it’s not worth it,’ ” Wilde says. “And it’s not their fault. They’ve been raised with this kind of innate misogyny as a part of their society: ‘If I don’t take up enough space, I won’t seem valuable.’ Actresses—highly trained, highly valuable actresses—have appeared in supporting roles in countless films. We don’t think about it in terms of, ‘My role is not as big as his.’ It’s, ‘Oh, it’s a good role. It’s a role where I have a brain.’ ”
Since the first indications that they were a couple arose, Wilde and Styles’s relationship has been subjected to the glare of widespread obsession, envy, and tabloid-fueled cattiness. The celebrity press has been particularly harsh on Wilde, professing to be scandalized that a woman in her 30s should dare to find love with a man 10 years younger. “It’s obviously really tempting to correct a false narrative,” Wilde says, with rueful composure, when I ask if she’d like to address the furor. “But I think what you realize is that when you’re really happy, it doesn’t matter what strangers think about you. All that matters to you is what’s real, and what you love, and who you love.” Wilde connects the uncommon attention focused on her, a very famous person, to the ordinary kind that all of us face on social media. “In the past 10 years, as a society, we have placed so much more value on the opinion of strangers rather than the people closest to us,” she says. But, she adds: “I’m happier than I’ve ever been. And I’m healthier than I’ve ever been, and it’s just wonderful to feel that.”
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.
When Wilde and Styles vacationed together this summer on a yacht in Italy, headlines made it seem that Wilde had all but abandoned her children to satisfy her own selfish needs. But Wilde sees her own well-being as connected to that of her kids’. “Parenting forces you to be honest about how you live your life. It puts in sharp, clear focus decisions you’re making,” she tells me. “I think we owe it to children to be happy. They sense it. They’re so intuitive. The idea that you can trick your kids into thinking you’re happy is ludicrous.” And what, she wonders, is really going on when the outside world passes judgment on how she—on how anyone—chooses to live? “You can go deep on Cold War influences on family structure, why we all think we need, you know, a two-parent household and a microwave,” Wilde says. “It’s very easy to control women by using guilt and shame, and I have no time for misplaced guilt and shame. The work I’ve done personally in the last decade has been learning to have a voice, and taking my voice seriously.”
The intimate relationships that Wilde is eager to discuss are those with her colleagues. She raves about her Don’t Worry Darling team, which, in addition to Silberman and Libatique (who joined her in the California desert for these images), includes the costume designer Arianne Phillips and the production designer Katie Byron. Her enthusiasm for her colleagues’ work inspires a rare devotion.
“A lot of artists want to present a new system for creating their work, but Olivia actually embodies this element of change,” Byron tells me. “I think it comes from her own level of self-confidence, and her own sensitivity and intellect.” Needless to say, this is not the domineering old Hollywood standard. “The craziest thing that I noticed about working with her is that we wanted to do our best job out of love, instead of out of fear,” Byron says.
Unsurprisingly, Wilde has a special touch when it comes to directing other actors. “When you’re an actor, and someone comes up to you and says it’s not working,” says Beanie Feldstein, “the first thing you start to do is feel terrible about yourself and put up your guard. But she knew exactly how to talk to us, because she spoke to us the way she wishes she was spoken to in the past.”
Wilde and Feldstein first met in 2017 in New York City, when Wilde was starring in the Broadway production of 1984. (The part was so physically demanding that she broke her coccyx.) At a party, Feldstein caught sight of “this angel in red” and was shocked to discover that the angel knew her name. “I was like, ‘I think I’m the only person named Beanie in here, but there’s no way Olivia Wilde is talking to me.’ ”
Feldstein reminds me that Wilde went out on a limb to cast her and Kaitlyn Dever in their first leading roles. “She gave so many people their first film opportunity with Booksmart, whether it was behind the camera in the crew, or in front of the camera,” Feldstein says. “We all just championed her, because she championed us.”
Almost 20 years in Hollywood has attuned Wilde to its entrenched inequities. She grows passionate as she tells me how outrageous it is that the phrase “the talent” is used to refer to the cast, but not the equally essential crew; she praises the courage and commitment of stuntpeople. “We have to evolve again,” she says. “The crew’s health has to be more important than the bottom line, and at the moment it’s not at all.”
Wilde originally planned to play Alice herself in Don’t Worry Darling. Then she went to see Ari Aster’s Midsommar, and was blown away by the captivating young woman being terrorized by a group of murderous Swedes onscreen. “Anytime there’s new talent, it’s thrilling,” she tells me. Wilde opted for a supporting role, which proved sufficiently challenging. “All the people I asked for advice on how to direct and act in your own movie were men,” she says. “And they all said, ‘Oh, it’s easy, do it!’ And now I realize it’s because they wore comfortable shoes, and their characters are never in corsets.”
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.
Wilde knows her Hollywood history; she herself could be our guide. She explains that women dominated the craft of film editing early on, because cutting and stitching together film strips was considered akin to sewing, and walks me through the Wizard of Oz shot that took Dorothy from black-and-white Kansas to Technicolor. I’m delighting in Wilde’s gleeful-nerd side, but after nearly three hours, we both need a break. In a temporary exhibit devoted to the work of Hayao Miyazaki, Wilde lies down on a tilted disc of bright-green grasslike material that’s meant to give visitors a chance to pretend that they’re in one of the master animator’s films. “I recently took mushrooms in a park and looked at the clouds with my best friend,” she murmurs as she gazes up.
In a room devoted to the art of casting, Wilde pauses by a glass case displaying annotated Polaroids of soon-to-be-famous faces, among them Christian Bale, Scarlett Johansson, and Salma Hayek. Wilde interned for the casting director Mali Finn when she was still in her teens; the experience taught her to show up with her own interpretation of the role. Better to be gutsy and wrong; you might just convince someone that you’re right.
Wilde is certainly still acting—she has an upcoming role in Damien Chazelle’s Babylon, set in 1920s Hollywood—but she has at last managed to break out of the space where she had to represent, as she says, “this idealized version of a woman. And I felt really thrilled to get older. It’s great when you get too old to play dumb.” What goes for art goes for life, too. “As you get older as a woman, you put up with less bullshit,” Wilde says. “I’m only willing to surround myself with people who are positive, and root for others. I choose kindness. I choose joy.”
In this story: hair, Edward Lampley; makeup, Grace Ahn; set design, Mary Howard / MHS Artists; production, View Finders NYLA