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 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."

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.

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.

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."