The Transformation Of Olivia Wilde From Childhood To 38 Years Old

Long before her romantic relationships were mined for tabloid stories, and long before her talents brought her to Tinseltown, Olivia Wilde was a kid growing up in the Washington, D.C., area. Raised by two parents who were not actors themselves (more on that in a bit), she was always encouraged to follow her own path. "[My mother] just took me so seriously when I said I loved something or wanted something," Wilde told Vogue in 2021. "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.'" 

After establishing her acting career, Wilde decided to get behind the camera and try her hand at another piece of film production — and gender inequality in the entertainment industry influenced this move. "I always wanted to make movies and be a part of the moviemaking process," Wilde told Variety in 2020, "I always assumed acting was the way in, because for many young women ... they're told, 'You love movies — you should be a movie star.' No one tells a little girl, 'Why don't you become a director?' It's just not a part of the conversation."

Wilde balances motherhood, acting, directing, and activism all while making the juggling act look effortless. Keep reading to find out how the star transformed into the multifaceted woman she is today.

Olivia Wilde's parents boast some remarkable resumes. The actor's father, Andrew Cockburn, is an accomplished journalist and published author who has written for the Los Angeles Times, The New York Times, National Geographic, and other notable media outlets. He is also an editor for Harper's magazine. Wilde's mother, Leslie Cockburn, is an investigative journalist who has worked for CBS, NBC, and more. She also ran for election to the U.S. House to represent Virginia's 5th Congressional District in 2018.

Wilde's parents' careers meant the star had many opportunities that most kids could only dream of. As she recounted in GQ, celebrities frequented her childhood home in Washington, D.C. — and we're talking top of the A-list celebs. Can you imagine walking into your living and seeing Mick Jagger chatting it up with your parents? Well, this was Wilde's reality. The "Alpha Dog" star was also cared for by famous author and journalist Christopher Hitchens as a child. 

Hitchens recalled Wilde's mischievous moments in a piece he wrote for Elle in 2010, just one year prior to his death. "Olivia's incandescent greenish-blue eyes seemed to miss ­nothing," the late author penned. "This was a house where there was a great deal worth observing, and family lore soon incorporated the evening where she was found eavesdropping on a dinner that featured both Mick Jagger and Richard Holbrooke." As if young Olivia Wilde's celebrity connections weren't impressive enough, she also spent her summers in Ireland throughout her childhood.

Olivia Wilde's lavish lifestyle continued into her teen years. She attended the prestigious Phillips Academy, a boarding school in Andover, Massachusetts, which just so happens to be one of the finest schools in the country, and an expensive one at that. As of 2022, annual tuition for a boarding student is over $66,000. Wilde graduated from the posh institution in 2002, so calculate how much her tuition cost accordingly. 

According to Business Insider, Phillips has an acceptance rate of only 13%, so it seems safe to assume that Wilde was an exceptional student. She also spent some of her high school years at Georgetown Day School in Washington, D.C. As of 2022, the pricey private school can cost over $46,000 to attend each year.

Wilde's high school years career was particularly formative because it was during this time that she decided to change her name. The star's last name was originally Cockburn before her mother convinced her to take on a pen name, according to a 2007 interview with Observer. Although this may seem unusual to some, pen names are common in Wilde's family. "My mother thought it was a good idea for me as well, so I could have my own identity outside of my family," said of her decision to take on the surname of poet Oscar Wilde. "She suggested I pick something Irish and something that I'd always be inspired by."

Olivia Wilde's college years were wild, to say the least, and not for the reasons you might think. During this point in the soon-to-be actor's life, she decided to pursue a future opposite of what was expected of her. She was accepted into Bard College in New York but as she told Women's Health, she ultimately decided to skip the college experience entirely. The then-budding star made another shocking decision during this time: She married a prince at only 19 years old, temporarily making Olivia Wilde a princess. 

Wilde tied the knot with Tao Ruspoli, the son of the Prince of Cerveteri in Rome, Italy. The couple's first wedding took place on a school bus, but they later had a more traditional ceremony at a property Wilde's family owns. The future director admitted to Women's Health in 2008 that she was hesitant to give the prince a chance in the first place. "[A mutual friend] wanted to introduce me to this Italian guy who made films and lived on a school bus," she shared. "I said, 'Woah! I don't want to meet a dude who lives on a bus!" The pair split in 2011.

After being accepted into Bard, Olivia Wilde was offered an internship in Los Angeles with casting director Mali Finn. As she told Women's Health, she decided to pass on college after a few successful auditions. Wilde's first acting gig was in the 2004 film "The Girl Next Door." She went on to land a larger role in "The O.C." In the second season of the hit series, she played Alex Kelly, a bisexual character who developed a relationship with Marissa Cooper (Mischa Barton). In a 2019 The New York Times interview, Wilde reflected on how her feelings regarding the primetime drama have evolved.  "I'd be like, 'I did a teen soap—what an embarrassment,'" she said. "And now I think, ah, that was really formative and I'm lucky I got to do that."

The actor also appreciated what the role meant to those who could relate to Alex Kelly. "When I started acting and one of my first jobs was playing a bisexual teenager on 'The O.C.', nothing about it scared or shocked me," Wilde told The Advocate in 2016. "I was just surprised by the enormity of the response. I still have women coming up to tell me they started discovering their own sexuality because of The O.C." Aside from serving drinks to Newpsie kids at the Bait Shop, one of Wilde's less well-known early TV gigs was on Fox's "Skin." The show only lasted one season, so this wasn't exactly Wilde's breakout role.

Olivia Wilde's acting career looked promising as she began to enter her early 20s. In 2004, she landed a role as Remy "Thirteen" Hadley on the popular Fox drama "House." The role introduced Wilde to a larger audience for the first time and gave her the potential to become a household name, although whether or not she ever reached that status is debatable. Like the part she played on "The O.C.," Thirteen was a bisexual character, and by all accounts Wilde was thrilled to portray her sexuality.

The actor told The TV Addict in 2009 that she enjoys playing parts that spark conversation and subvert expectations. "I'm not afraid of a challenge and I think it's interesting that people have such a huge reaction to my characters," she said of her attention-grabbing Fox roles. "I think it's interesting to play ambiguous characters. It's less interesting to play someone cut and dry one way or the other, and I don't just mean in terms of sexuality, I mean anything about their personality." She went on to explain that she actually enjoys defending her characters against critics.

Wilde's time on "House" came to an end in 2011 when she left the show to film "Cowboys & Aliens." Luckily, there was no bad blood between the busy actor and the show's production team following her departure. "House" executive producer Katie Jacobs told Entertainment Weekly, "We're very proud of her and very happy for her."

It's no secret that show business isn't necessarily kind to women as they get older; a Time report from 2015 found a female actor's career "peak" hits at age 30. But before Olivia Wilde hit this milestone age, she wasn't too worried about leaving her 20s. In a piece for Glamour titled "Dos and Don'ts of Turning 30," she wrote "People assume actresses are afraid to get older; the truth is the roles get a whole lot more compelling once you're too old to play dumb. So I'm welcoming this development with open arms, and so should you."

Wilde went on to give tons of humorous, albeit helpful advice, including how to embrace the wisdom that comes with age. One example: "Your twenties were for 'ducking up,' as my auto-correct would say, and learning from those mistakes. (For instance, never again will I convince myself that sleep is for sissies and go straight from a party to the airport. You will not "sleep on the plane"; you'll vomit in the security line. Go to bed.)"

This wasn't the only time Wilde has opened up about being more than okay with getting older. In 2019, she spoke to The New York Times about how her career became more dynamic after she exited her 20s. Wilde explained that she was finally old enough to be considered for roles that weren't solely reliant on sex appeal.

By her mid-20s, Olivia Wilde found love again, this time with Jason Sudeikis. Wilde first crossed paths with the "Saturday Night Live" alum at a finale party for the show. It seems that the initial encounter was love at first sight, but the first move would have to wait. "I met Jason, and I thought he was so charming," Wilde told Allure (via People). "He's a great dancer and I'm a sucker for great dancers. But he didn't even get my number."

She went on to explain that although they did not exchange contact information until some time later, they continued to build a connection. "Over the next six months we kept running into each other," she told Allure. "[One night], my best guy friend walked up to him and said, 'This is Olivia's number. Use it.' That was the beginning." Wilde and Jason revealed they were engaged in 2013. The couple later welcomed their son, Otis Alexander Sudeikis, in 2014. Wilde shared a photo of her holding her firstborn to Twitter to announce the news. Two years later, Wilde took to Instagram to announce the birth of their second child, Daisy Josephine Sudeikis. 

Although the couple had two children together, they never officially tied the knot. In 2014, Wilde explained to Glamour that she wasn't in a rush to marry her beau because the two were confident they were fully committed.

In 2019, Olivia Wilde's directorial debut, "Booksmart," hit theaters. The coming-of-age film follows two high school seniors as they go through a rebellious phase on their last day of school. In a chat with Variety about the process of directing the movie, she revealed that she first developed an interest in directing on the set of "Tron: Legacy." Wilde wanted to have a say in her character and the storyline of the movie, and luckily for her, the film's producers were willing to let her tweak things a bit. "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," she said.

Just one year after the release of "Booksmart," Wilde faced another major life change when she split from fiancé Jason Sudeikis. The former couple stayed silent about the breakup until Sudeikis finally shared his side of things during an interview with GQ in 2021. "That's an experience that you either learn from or make excuses about," the "SNL" alum said of the breakup. "You take some responsibility for it, hold yourself accountable for what you do, but then also endeavor to learn something beyond the obvious from it."

Olivia Wilde's directorial followup to "Booksmart," "Don't Worry Darling," follows a 1950s housewife (Florence Pugh) who discovers dark truths about her seemingly perfect life with her husband (Harry Styles). As reported by Variety, Wilde revealed more about the plot of the film while speaking to an audience at CinemaCon. "I want you to imagine a life where you have everything you could want," she said, painting a picture of the utopia in which the story unravels. She then asked the audience if they would ever give up that ideal life if push came to shove, asking, "What are you really willing to sacrifice to do what's right?"

"Don't Worry Darling" likely means a great deal to Wilde, not only because it is the second movie she has directed, but because she met her new boyfriend while filming. A source told Us Weekly, "Harry and Olivia had chemistry almost instantaneously on set. It was only a matter of time before they got together." While both parties have been relatively quiet about their romance, they have offered up glimpses into their relationship. 

In late 2021, Vogue asked Wilde about the rumors involving a certain One Direction alum. Though she did not get too specific, she did reply, "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." At 38 years old, Wilde seems to be exactly where she wants to be in both her career and her love life.