Say what you will about Olivia Wilde’s career, but it’s rarely been dull. For that, the director and star of the newly released Don’t Worry Darling can thank her parents.

In a recent Vanity Fair cover story, Wilde acknowledged that one of the most motivational mantras Andrew and Leslie Cockburn delivered unto their daughter whose change in last name as an actress was an homage to Oscar was a simple three-word phrase: “Don’t be boring.”

“It affected every decision,” Wilde told Vanity Fair. “Any crossroads I came to where there was one option that was safer than the other, I would take the less safe route. That led to some great things, like taking a chance on being an actor.” It also led to her becoming a director, but we’ll get to that soon enough.

Even before she made her life’s debut in New York City on March 10, 1984, Wilde was surrounded by drama, with her mother an investigative journalist having been evacuated from a flight in the Middle East due to an onboard bomb while she was pregnant with Wilde. Raised in Washington, D.C., Wilde started her educational career at Georgetown Day School before heading to boarding school at Phillips Academy in Andover, Massachusetts. The acting bug had already bitten her by the time she graduated in 2002, which led her to the Gaiety School of Acting in Dublin, Ireland.

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A cursory look at Wilde’s filmography reveals that work came quite quickly for the budding young actress upon her return to America’s shores: she stepped into a series-regular role on the FOX drama Skin, playing daughter to Ron Silver and Pamela Gidley. Doesn’t ring a bell? That’s because it was canceled after only six episodes.

“One day all these people were bowing down to me and throwing free clothes at me and telling me I was the best thing since sliced bread, and the next day…all of that disappeared,” Wilde said in a 2016 Elle article. “That was great for an 18-year-old to learn, and I will never again take the bull seriously.”

Fortunately, FOX quickly came calling again, with Wilde doing 13 episodes of The O.C. as Alex Kelly, a bisexual bar owner who had flings with both Seth Cohen (Adam Brody) and Marissa Cooper (Mischa Barton). In the midst of these two TV gigs, however, Wilde was also breaking into the movie business, picking up roles in The Girl Next Door, Alpha Dog, Turistas, and as if anyone would forget a title like this one Bickford Shmeckler’s Cool Ideas.

Wilde’s next TV gig was on NBC’s The Black Donnellys, another series regular role that didn’t last significantly longer than Skin, getting its walking papers from the network after only a single season. As history reveals, however, it proved to be a career-making cancelation for Wilde, as it freed her up for the role that truly set her down the path of mainstream stardom: playing Remy Hadley, a.k.a. Thirteen, on House.

If you remember Wilde’s stint on the series, then you probably also remember the Survivor-esque way her character ultimately found her way into her permanent status at Princeton– Plainsboro Teaching Hospital. While it was nerve-wracking for viewers, who had no idea which of the doctors would make the cut, Wilde ultimately didn’t care whether she made it to the bitter end or not.

“I really was having so much fun with the eight episodes that I knew I would have that I wasn’t even really thinking ahead,” Wilde told the Futon Critic in 2009. “It was just such a blast to be in that group of people that were going to possibly be the new doctors, possibly not. We had such a fantastic time. It was really one of the highlights of my career. It’s a rare opportunity to be able to say material that’s as intelligent as that. And to be able to play an independent, professional women is rare, so I was honored to be on one episode of House. And then it got to eight, and it was like, ‘Maybe this is the last one.’ And then finding out that I got to be part of the family was just incredible.”

Wilde’s run on House lasted from 2007 to 2012, and although she was only appearing in a recurring capacity for that final season, there’s a good reason for that: she was doing an insane number of films. Between 2010 and 2012, Wilde appeared in The Next Three Days, Tron: Legacy, Butter, The Change-Up, Cowboys & Aliens, In Time, On the Inside, Deadfall, People Like Us, and The Words.

It’s arguable, however, that the most important project of Wilde’s career during that era was, in fact, none of these feature films but, rather, the 2011 short film Free Hugs.
Why? Because it was her first step behind the camera: she wrote, directed, and even had a small role in the film, which she did for Glamour Magazine. (Check it out, kids: it’s on YouTube!) From there, Wilde directed a few music videos – Edward Sharpe and the Magnetic Zeros’ “No Love Like Yours” and Red Hot Chili Peppers’ “Dark Necessities” – before finally getting her shot at a major motion picture: 2019’s Booksmart. All things being equal, though, she would’ve loved to have made that jump sooner.

“I always wanted to make movies and be a part of the moviemaking process,” Wilde told Variety. “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. But if a little boy says he loves movies, it’s like, ‘Maybe one day you’ll direct. Maybe you’ll be the next Steven Spielberg or Martin Scorsese.’”

Fortunately, Wilde overcame the odds, finding tremendous acclaim with Booksmart, which currently holds a 96% rating on Rotten Tomatoes, and she earned the opportunity to take a shot at an even higher profile film: Don’t Worry Darling, starring Florence Pugh, Harry Styles, Gemma Chan, Chris Pine, and Wilde herself.

“It’s harder for women to get a second chance at directing,” Wilde told Variety. “Fewer people will invest in the second film of a woman than a man. I was so lucky. [Booksmart] didn’t make a billion dollars. It struck enough of a nerve of the cultural zeitgeist that I was allowed to have another opportunity. I really feel, at this point, that I have earned the right to say I’m a director.”