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1980s

Off to a Good Start

Born Olivia Cockburn to renowned journalists Leslie and Andrew Cockburn, Wilde realizes she wants to be an entertainer at a young age. "First I wanted to be Einstein – then an actress," she later recalls of her youthful ambition, which is cemented at the prestigious Phillips Academy boarding school in Andover, Mass.

2002

Irish Spring

Upon graduation, Wilde studies at the Gaiety School of Acting in Dublin (because her father is Irish and her mother is American, Wilde is a citizen of both Ireland and the United States). "There is a certain humility that goes with the acting business in Dublin that I could not have learned elsewhere," she says of her time in Ireland. The budding thespian moves to Los Angeles in 2003 to pursue acting professionally, upon which she adopts the stage name Olivia Wilde. "Oscar Wilde is someone who I respect for so many reasons – a revolutionary, a comedian and a profound thinker," she says.

2003

Olivia Wilde

June

A Royal Pair

At a party in L.A., Wilde meets filmmaker Tao Ruspoli, who also happens to be Italian royalty. After six months together, the 18-year-old actress and her 26-year-old prince elope on an old school bus. "We got engaged at Burning Man and married on a school bus. We were not conventional," she tells Glamour of her low-key nuptials. They eventually do it up right, holding two more ceremonies: one at her parents' farmhouse in Virginia, the other in the garden of her husband's Italian castle.

Olivia Wilde

October 20

'Skin' Is In

Wilde nabs her first professional role as Jewel, daughter of a pornographer involved in a star-crossed affair, in the FOX series Skin. While the show, from producer Jerry Bruckheimer, shows promise, it's canceled after three episodes. The actress soon hits the big screen in 2004's The Girl Next Door.

2004

Olivia Wilde

November 18

A Lingering Kiss

Wilde leaves her mark on fans of The O.C. when she stars as Mischa Barton's bisexual lover, a role that catapults her to fame. "I continue to get letters from girls around the world who thought that there was something wrong with them if they recognized it in their own sexuality," she tells PEOPLE of the memorable guest stint on the FOX series.

2007

Olivia Wilde

October 02

'House' Call

After starring in NBC's short-lived crime drama The Black Donnellys, Wilde dons doctor's scrubs for FOX's House, where she plays reckless physician Dr. Remy "Thirteen" Hadle (who also happens to be bisexual). "Right from the first day," her costar Hugh Laurie enthuses to GQ, "Olivia was pretty hard to ignore."

2009

Olivia Wilde

May

Hot Shot

With her career heating up, the actress tops Maxim's Hot 100 list, and later shows off her svelte frame in a bikini-clad GQ cover. "The only role I really don't understand is this recent sort of 'sexiest-vixen' thing," she tells the men's mag. "It doesn't feel like me, doesn't feel natural."

2010

Olivia Wilde

November 17

'Tron' Voyage

Joining the highly anticipated sequel to the 1982 cult film, Wilde stars as a butt-kicking cyber babe in Tron: Legacy, which requires her to fill out a formfitting costume. "I saw the boobs on the suit, and I said, 'Oh, hell no,'" she told Details. "I'm doing kicks and backflips in this thing?" The film rakes in over $44 million to take the No. 1 spot at the box office on opening weekend and helps Wilde land another plum part in 2011's Cowboys & Aliens.

2011

Olivia Wilde

February 08

Fairy-Tale Ending

After eight years together, Wilde announces her separation from husband Ruspoli, and later files to end her marriage. Shortly after, the newly single star is spotted with a slew of Hollywood hunks, from Ryan Gosling to Ryan Reynolds. "[Being famous] makes dating harder," she tells Marie Claire of the romance rumors. "You go on one date and everyone thinks you're dating."

Olivia Wilde

December 29

A New Man

Two months after finalizing her divorce, Wilde gets cozy with Saturday Night Live funnyman Jason Sudeikis at a Jayhawks basketball game in Lawrence, Kan. Days later, the actress – who doesn't comment on her relationship status – lets her hands do the talking during a romantic stroll with the actor in New York.

Photo Credits

BIOGRAPHY (top to bottom): Giulio Marcocchi /Getty; Warner Bros; FOX; Chris Haston/FOX/Everett; Courtesy of GQ; Everett; Charles Sykes/AP; Jamie Squire/Getty

Edited by Julia Wang

Olivia Wilde

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