The Untold Truth Of Olivia Wilde

Actor Olivia Wilde has been a firm fixture of TV and film for most of her adult life, and yet the Washington, D.C. native never managed to scale the heights of contemporaries such as Jennifer Lawrence. Although Wilde has enjoyed a varied and successful career, and in spite of several predictions about her hitting the big time proper over the years (whatever that means), she didn't quite make it to It Girl status.

With the release of her barnstorming directorial debut Booksmart in 2019, it appeared to all have been by design. Or, if not, Wilde was at least content to remain relatively anonymous as her fellow celebs found themselves unable to even leave their homes without being swarmed by paparazzi. From paying homage to Joan of Arc to cutting her teeth first as a casting assistant and then as a wannabe film-maker actively observing those working on set alongside her, Wilde has never played things by the book.

She keeps her cards relatively close to her chest but, over the years, she has revealed fascinating elements of her personality more than worthy of further excavation. This is the untold truth of Olivia Wilde.

Following in the footsteps of Katy Perry (real name: Katherine Hudson), Olivia Wilde's real name isn't actually Olivia Wilde. In an interview with The Observer, the actress explained pen names are a tradition in her family, the Cockburns (okay, maybe it made sense to change it). Wilde wasn't a random choice, either. Her mother suggested an Irish surname, in keeping with the family's heritage, as well as something to inspire the young woman to follow her creative pursuits. 

"I was doing The Importance of Being Earnest — I was playing Gwendolyn, and I was so in love with it," she recalled. "Oscar Wilde is someone who I respect for so many reasons — a revolutionary, a comedian and a profound thinker. I had all these reasons — but what I didn't foresee is that people would think of it as a sexy adjective. So now it's got a pornographic quality I never considered." Surely not as much as Cockburn, though, right?

The 2010 sci-fi sequel Tron: Legacy was a major breakout moment for Wilde (one of many, none of which would propel her to the A-list as expected — more on that below). Playing tough, sexy warrior Quorra, the role found Wilde branching out in a big way, with the actress describing it to Den of Geek as, "The biggest departure from myself that I've played." The part also required a hell of a lot of training, including Kapoeira, Jiu-Jitsu, cross training, and several different varieties of fight training.

Wilde had to fight in heels but, rather than complaining, she rose to the challenge (no pun intended). "I just wanted to be as strong as possible, and do as many of the fighting stunts as I could myself," she explained. "But... it was quite a challenge. Running in heels isn't easy, kicking in heels isn't easy, but it made it all more bad-ass in the end." 

Wilde utilized her outfit to get into character, noting, "The suit is like armor for her. One of the most influential characters in history, who I used as research for Quorra, was Joan of Arc, who of course fought in chain-mail from head to toe." 

Wilde has a refreshingly healthy attitude to food — more concerned with looking strong than sexy. She told Women's Health about playing hooky from school to watch cooking shows, and even bragged about winning an eating contest in Australia — much to the disbelief of the many men involved. "I ate 33 pancakes in 20 minutes, and I only did it because they said a girl could never enter the competition. I won against these giant men, and they were convinced I was cheating. Guys have some sort of sick fascination with girls who can eat," she recalled.

In contrast, it's other women who encourage her to stay skinnier, even when it might be adversely affecting her health. While on a trip to Thailand with her ex-husband, Wilde got very sick with Dengue fever and dropped 15 pounds. "I looked really thin, and all the men in my life were worried about me. But all the women in my life were proud of me. They started calling it 'the Dengue diet,'" she revealed.  

After choosing a stage name that pays homage to her Irish heritage, it's no surprise to learn Wilde spent many of her formative years on the island itself. In an interview with The Independent, she reminisced about summers spent in Ardmore, County Waterford.

"It was amazing. I feel like the luckiest child in the world because I got to grow up there. ...During the year, I would go back to the States, and all year long really couldn't wait to get back to Ardmore," she trilled. Far from a big city kid slumming it with the locals, Wilde actually preferred Waterford, admitting, "I found Ireland much more inspiring as a kid, much more fun, and the people had such an amazing effect on me. I credit a lot of my growth as a child and a lot of my happiness with the people I was surrounded by in Ireland."

Wilde didn't write Booksmart (that credit goes to the combined, and considerable, talents of Emily Halpern, Sarah Haskins, Susanna Fogel, and Katie Silberman), but that doesn't mean the actor-turned-director couldn't see shades of her own high school experience in the movie. Speaking to The Guardian, Wilde revealed that her school, the prestigious Phillips Academy in Andover, MA, was filled with characters just like Beanie Feldstein's overachieving, no-nonsense Molly.

Describing Phillips as "very academically rigorous and competitive," Wilde explained, "It was all about working hard enough so that you get into the Ivy Leagues, so that you can become a leader of the free world or whatever." She admitted to feeling frustrated by the experience because, as her Booksmart characters learn over the course of one raucous high school night, there are more important things in life than just studying. 

"Where's the rest of the human experience? There must be room to be really smart and love books and also love music and people and theater and sex and frivolity," quipped Wilde. 

Wilde is known for playing not one but two boundary-pushing bisexual characters over the course of her career, namely Dr. Remy Hadley, AKA Thirteen, in House, and the super-cool Alex in The O.C. Bartender Alex's same-sex relationship with popular girl Marissa (Mischa Barton) is tame in modern terms, but back in the day it was a huge deal. In an interview with Elle, Wilde admitted she, too, thought it was super progressive at the time, noting, "We thought we were so woke in 2003! So much has changed, it's incredible."

Although it took her a while to appreciate the soapy teen show as a formative experience, Wilde now fully understands its importance to a generation of fans. Appearing on the Keep It podcast, she revealed, "At the time I was like, 'Well this should be normal. Why is it such a big deal?' But people either got riled up in a good way or got riled up in a bad way. And I was like, 'Well this is an important conversation.'" The actor went on to explain people still approach her to say thanks for helping them come out. 

Considering Wilde kicked off her Hollywood career by acting as assistant to a casting director, she's in a pretty good position to opine on the state of the movie business. When questioned by The Playlist about how she assembled the players for her feature debut, Wilde took the opportunity to openly criticize how actors are chosen for projects, suggesting it's more about social media followings than talent. 

"The criteria for casting has been warped for far too long. ...It makes it a more complicated process to market, but you just have to be more creative. It forces the movie to be good enough that it sells itself," she said, referring to choosing the little-known likes of Feldstein, Kaitlyn Dever, Billie Lourd, and Noah Galvin for Booksmart. 

Wilde believes change should come from the top down, too, telling Vanity Fair, "The only way we're going to make any headway as female directors in this industry is if more people take risks on new talent."  

In keeping with her desire to learn by doing, Wilde didn't take the traditional film school route — instead, she educated herself while working on the sets of other people's movies. As she explained to Vanity Fair, the desire to take more creative control was always there. "I remember being on the set of Tron [Legacy], at age 25, and really wanting to do more to control the story-line of my character, and wanting to have a bigger voice in the creative direction," she advised.

Thankfully, her bosses were open to giving Wilde some input into the creative process. She noted, "It was an awakening of sorts, because, while they were being very generous and allowing me to speak up, that wasn't happening on other sets, and I just felt like I needed more actual control." 

Still, she was insecure about finally taking the reins. As Wilde admitted to The Guardian, "I just didn't realize that my 15 years on set as an actress had actually been my de facto film school and then I'd been spending that time shadowing great directors and also learning from bad directors. Bad professional experiences are just as valuable as cautionary tales." 

Given that it took her 15 years of high-profile acting work and a critically well-received directorial debut to finally be taken seriously by Hollywood, it's no wonder Wilde is sick of being seen as just "the pretty girl." In a lengthy, career-spanning interview with The New York Times, Wilde stated she's tired of being cast based on looks alone. 

Telling the publication she's "too old to play dumb anymore," Wilde noted plainly, "It is remarkable that... [Booksmart] is the first job I've ever had that wasn't entirely dependent on and connected to my looks. It grosses me out to acknowledge it, but I've been thinking a lot about it." With her first feature and passion project, she explained that she "was there only because of my brain and my heart. And the sense of fulfillment that comes from that is really massive. It's a profound shift for me." 

As for her acting career, Wilde worried whether it was "ever truly purely me, or was it always something that was fraught with a sense of superficiality, of being judged from the outside in an external way?"   

With the likes of Wonder Woman and Captain Marvel, women were finally given the opportunity to take on a superhero landscape previously run and populated almost exclusively by men. Speaking to MTV International Wilde suggested she would "totally... absolutely" be open to following in the footsteps of her female forebears by directing a Marvel movie some day, if the opportunity presents itself.

"I think that it's exciting that now women like Ava DuVernay and Chloé Zhao are directing Marvel films and it's exciting to think about what that will do to the franchise. ...I'm a proud member of the movement of female directors, and I don't think there's any genre that should be off the table," she said.  

DuVernay was tapped to direct The New Gods, which is actually a DC property, while Zhao was tackling The Eternals for Marvel. Wilde's choice of comparative film-makers is interesting here as Zhao, in particular, broke out in a huge way with her sophomore indie feature, The Rider, in 2017 (similar to Wilde with Booksmart). 

Reed Morano, the first woman to direct Wilde in a movie (2015's Meadowland), was a rock for the actor-turned-director when it came time to helm her own feature. Wilde told Den of Geek that Morano was a constant source of support and inspiration to her while making Booksmart. "I talked to Reed every day," she noted, admitting Morano was a little peeved her friend was getting to make her high school movie first. 

However, regardless of professional jealousy, Morano was "really inspiring, and I think she reminded me of what had worked so well on her directorial debut, which I produced and I was in, and I was there with her for every minute of that. But she reminded me of the lessons she had learned." Wilde also advised their friendship was extra fruitful because, "I was making a film about female friendship, leaning on my female friends to help me make the best version of it that I could." 

Although Wilde was chomping at the bit to "make it" in Hollywood when she first started out as an actor, looking back with The New York Times she realized it was better to have not become the It Girl she was always striving to become. "I had security experts saying I was going to have to put protective steel shields on my windows. And of course that didn't happen," she mused on her supposedly impending celebrity around the release of Tron: Legacy.

However, where many performers would feel disappointment, Wilde was optimistic about her career trajectory, keeping those experiences close to her heart. "I somehow developed a solid core of confidence that has allowed me to weather the storms of almost everything not working. None of this is commitment. This is me learning, and then realizing, I know what I want to do with it," she opined, comparing the process to finding the right romantic partner.  

Wilde has learned something from every director she's ever worked with, from Morano to Spike Jonze, who told The New York Times that Wilde is "Driven, really, by an excitement to make things and to learn, and to try things she doesn't know how to do." He encouraged the actor to try out directing, saying: "You don't know if you're a filmmaker until you do it. It's a trial by fire". However, when it came time to make Booksmart, Wilde looked to another legend for inspiration. 

In particular, she operated a strict no scripts on set policy, telling Hollywood Life, "It is effective but hard. It's a rule that Martin Scorsese started to make sure no one was walking on set still memorizing lines. He wanted everyone to be performance ready and for improvising that was a whole different conversation. Sometimes we improvised depending on the scene." Basically, it meant everyone had to be off book by the time the cameras rolled in, so no time was wasted — which, on an indie movie, is even more crucial. 

In an unexpected turn of events following a very Hollywood-esque trope, Wilde's teenage marriage to Italian filmmaker Tao Ruspoli actually lasted a good eight years. The two divorced in 2011, with the actress admitting to Marie Claire at the time that it was a formative experience for her. "The trauma of the whole thing has been humbling, and for the first time, I'm a little bit wobbly. I'm a case of arrested development, in a way — from spending your 20s with someone who really loves to take care of you, as my husband did. But I think it's very healthy to spend time alone. You need to know how to be alone and not be defined by another person." 

Wilde admitted to being scared to throw herself back into dating, struggling with the idea that she'd somehow failed by not making the relationship work. "It makes you a more empathetic person, and I think it's made me a better actress," she suggested. In the end, though, the self-described perfectionist acknowledged, "It's just that I'm a ridiculous romantic. I have very high standards for every part of life — my work, my relationships, food, love. I can't just pretend." 

Following a night of monologues hosted by Glamour magazine in New York, Vulture recounted Wilde's, er, wild post-divorce sexcapades before she settled down with husband, and father of her kids, Jason Sudeikis. In particular, according to her monologue, Wilde wanted to live by the rules of Olivia Land where, "Relationships can legally only last seven years, without an option to renew." 

Naturally, this idea didn't pan out as she's been sharing her life with Sudeikis since 2011. The two got engaged in 2013, have two kids, and they were reportedly finally ready to get married in 2018, but nobody seems quite sure if or when the couple actually made it official. 

In a post-show chat with Vulture, Wilde suggested women unsure if their partners are right for them should listen... to their lady parts. "Sometimes your vagina dies. Then you know it's time to go. There's no reason to sacrifice your womanhood and femininity for some sort of weird feeling of responsibility to something that may not be right. I feel like far too many women do that," she advised. Wilde also told the publication women should think with their genitals in the same way men do, to level the playing field. 

Although Olivia Wilde's directorial debut was a major moment for her, her sophomore feature, "Don't Worry Darling," courted significantly more attention — of entirely the wrong kind. The problems began when the first trailer dropped, and much of the press coverage surrounded a shot of co-lead Harry Styles performing oral sex on Florence Pugh's character. 

The "Midsommar" star admitted she wasn't pleased with the response in an interview with Harper's Bazaar. "When it's reduced to your sex scenes, or to watch the most famous man in the world go down on someone, it's not why we do it. It's not why I'm in this industry," Pugh argued. She added, "[This movie is] bigger and better than that." 

Wilde told the Associated Press that she actually wanted more sex in the trailer, since female pleasure isn't something that's typically shown onscreen, outside of LGBTQ+ movies. Rumors quickly circulated that all was not well between Wilde and Pugh, particularly since Wilde's leading lady notably wasn't promoting "Don't Worry Darling" on social media, per The Guardian. At the Venice Film Festival, the director refused to engage. 

Olivia Wilde found herself at the center of a brewing controversy when her portrayal of real-life journalist Kathy Scruggs in "Richard Jewell" was deemed to be in bad taste, as it seemingly implied Scruggs had traded sex for tips (per Variety). Wilde tackled the issue head-on in a series of tweets, which began with the assertion that, as an actor, she has less control over the character than she would as a director.

The "O.C." alum went on to note, "As a child of journalists myself, I have deep respect for the essential work of all in their field, particularly today when the media is routinely attacked and discredited." As British Vogue pointed out, her parents, Andrew and Leslie Cockburn, are both well-known reporters in their respective fields. He's enjoyed a prolific career in the U.K., while Leslie worked as a producer on "60 Minutes." 

Wilde's grandfather's cousin, meanwhile, was none other than "Brideshead Revisited" author Evelyn Waugh, while her cousin, Emma Tennant, is also a novelist. Her grandfather, Claud Cockburn, was a writer, too, and even fought in the Spanish Civil War alongside Ernest Hemingway.

Family comes first for Olivia Wilde, which is abundantly clear when you consider she has several tattoos dedicated to her nearest and dearest. As reported by E! News, during a Reddit "Ask Me Anything" session, the actor-turned-director revealed that the ink on her wrist is a tribute to her beloved uncle. "All love, A," it reads. As Wilde elaborated, "It's in honor of my late uncle Alexander Cockburn. He was a dear, dear friend. The tattoo is the last phrase he wrote to me. All love, A. It reminds me to love everyone, just as he did." 

In December 2021, she added to her growing collection with a couple of delicate script tattoos on her forearms. Courtesy of celebrity artist Dr. Woo, the ink is comprised of her two children's names: Otis and Daisy. Wilde also has another tattoo dedicated to her son, a pretty galaxy on her forearm (via Instagram).

Olivia Wilde and her first husband, Italian prince Tao Ruspoli, beat the odds by staying married for much longer than anybody anticipated, considering they tied the knot just six months after meeting for the first time, when she was just 19. The couple didn't do anything traditional for their big day; the Irish Mirror reported that Wilde and Ruspoli said their vows in the back of an old school bus.

As the actor admitted to Women's Health, Ruspoli was actually living on the bus in question at the time, and she initially didn't want to meet him when a friend tried to matchmake the two. "He wanted to introduce me to this Italian guy who made films and lived on a school bus. I said, 'Woah! I don't want to meet a dude who lives on a bus!'" she recalled.

Once they met, she was immediately charmed by his low-key lifestyle. Wilde's father, however, suffered "a minor heart attack" when he learned the happy couple planned to get married (via the Irish Mirror). A second wedding was later held at the Wilde family's farmhouse in Virginia, followed by a third at Ruspoli's family's literal castle, located just outside Rome.

The fact that Olivia Wilde married a man in an old bus makes slightly more sense when you learn she's actually a lifelong classic car enthusiast. The actor told Vanity Fair proudly, "I love classic cars, and I've owned a few in my life — a '59 Thunderbird, a '67 Mustang." However, she conceded they're not always the most reliable sets of wheels, admitting there have been many times when she's taken her friends out to show them how great her car is, only for it to completely conk out on her. That hasn't stopped Wilde from loving them, though.  

The prolific actor shared, "I had a '58 Chevy Biscayne that was kind of mint green and just beautiful — I always loved the Chevy Bel Air, but the Biscayne is cool because it has bigger hips; it's a bit more funky." Even if, as the "Booksmart" director acknowledged, the motor in question stalled right in the middle of fashionable West Hollywood during a girls' night out. "I started out as such a badass and ended up just really embarrassed," she joked to Vanity Fair.

According to HuffPost, Olivia Wilde was a strict vegetarian from the age of 12, and she's dabbled in veganism on and off as an adult (she's also flirted with being a pescatarian, per Allure). Revisiting how fellow actor Alicia Silverstone showed her the way while they were shooting the movie "Butter" in Louisiana, Wilde acknowledged, "[Being vegan] is not always easy and accessible, but it's a way of life and makes me as a person feel really good and physically look better." The "Don't Worry Darling" director added, "My skin was better, energy was better." 

British Vogue noted she was even voted PETA's sexiest vegetarian celebrity back in 2010. However, Marie Claire U.K. reported that Wilde divulged to Cosmopolitan how her nerves were tested following a difficult public split from Jason Sudeikis, which made her reach for the cheese. Still, Wilde maintains that she's vegan the vast majority of the time. 

Aside from her (rumored) feud with actress Florence Pugh, Olivia Wilde also courted controversy when it emerged that Shia LaBeouf wasn't actually fired from "Don't Worry Darling," as previously reported. Wilde initially claimed she had asked the actor to step back from the role that was ultimately played by her paramour, Harry Styles, because he had a "combative" attitude on set, as she explained during a Variety interview while promoting the film. 

"His process was not conducive to the ethos that I demand in my productions," Wilde revealed, asserting that she has a responsibility to keep everybody on the project safe and happy. But LaBeouf shot back that he'd chosen to exit the project due to a dispute over rehearsals, per ET. The actor shared an email exchange with Wilde, alongside text messages from around the time he left the movie, to prove his point. 

Elsewhere, a video of a voicemail Wilde had left him was leaked online, purporting to show the director begging LaBeouf to give the project another shot — and also seemingly blaming Pugh for not being a team player.

Shocking the world, in November 2020, People confirmed that beloved celebrity couple Olivia Wilde and Jason Sudeikis had called time on their relationship, thereby ending their seven-year engagement in the process. An insider confirmed, "It's been amicable and they've transitioned into a great co-parenting routine. The children are the priority and the heart of the family's relationship." However, just a few months later, at CinemaCon, it seemed like the former couple was anything but amicable. 

Wilde was infamously served what turned out to be custody papers while she was live on stage, with The Hollywood Reporter confirming the filmmaker was about to introduce "Don't Worry Darling" when she was approached by someone with a manila envelope. After quickly checking its contents, Wilde continued with her speech. "I hated that this nastiness distracted from the work of so many different people and the studio that I was up there representing," she told Variety, adding that it simply wasn't appropriate.

Wilde also tellingly revealed, "Sadly, it was not something that was entirely surprising to me. I mean, there's a reason I left that relationship." Sudeikis, meanwhile, claimed he had no idea when she'd be served (per Us Weekly).

For the most part, Olivia Wilde and Harry Styles have kept their relationship firmly under wraps. Even so, they've been besieged by negative attention, particularly from Styles' ravenous fans. As Wilde told Vogue, "It's obviously really tempting to correct a false narrative." But she added that she sees no reason to care about what others think, as long as she's happy. (It's worth noting her issues with Florence Pugh allegedly stemmed from the actor's disapproval about her director hooking up with Styles on set, while still involved with Jason Sudeikis, per Page Six.)

All the "Booksmart" director would say is, "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" (via Vogue). For Styles' part, he admitted to Rolling Stone that it's tough to watch someone he loves being subjected to such harsh criticism, but sadly, it's all part of the game. Wilde was even clearer in an interview with Variety, stating firmly that she would not be discussing anything publicly. "We both go out of our way to protect our relationship; I think it's out of experience, but also just out of deep love," she said.

Olivia Wilde actually has two iconic bisexual roles to her name, with Dr. Thirteen in "House" another major fan favorite in addition to her role in "The O.C." EW notes that the character exited "House" alongside her girlfriend, giving Thirteen the happy ending she deserved as far as Wilde and the viewers were concerned. During a chat with The TV Addict, the actor discussed how important it is to represent all facets of the LGBTQ+ spectrum on television.

"People assume that when someone makes out with someone of their own sex, they are gay. And I think it's great when people learn about the definition of bisexual, which means people can be attracted to both sexes," she explained. "I'm sick of people saying Thirteen is a lesbian. Why doesn't anyone pay attention to the fact that there is a possibility of this third type of lifestyle? I think it's important to represent that." 

Playing the fan-favorite character had another unexpected result, with Wilde revealing to The Advocate that women frequently hit on her, which she considers "an honor." As the "House" alum confessed, "When it's a woman, I always blush a little harder."