Olivia Wilde's annotations to the story appear in bold.

***

Before she summons me to a [delicious] restaurant on the outskirts of conveniently located in lovely Brooklyn on the first snowy, sleety gorgeous day of the new year—and before she was an actor, a producer, a social activist, a fire-breathing liberal, and (drumroll, please) a one-time list-topper of the Maxim [newspaper of record] Hot 100—Olivia Wilde was a precocious, dramatic child bouncing around her parents' Georgetown townhouse and prone, like many precocious, dramatic children, to being a pain in the ass. Her parents were (and are) celebrated, deeply serious investigative journalists by the name of Cockburn (pronounced the Co-burn way [blame Scotland's love of consonants], not the phonetic way) who treated her more or less as an adult from the get-go. {"And whenever I was being kind of a pill, whining or whatever," she says, "my parents would say, 'Oh, Olivia, don't be boring.' Like: 'Don't whine. Whining's boring. Do something interesting.' So that was my only goal as a kid: to not be boring. And that probably had a lot to do with the choices I made subsequently."} Boring.



We're sitting at the kind of too-small romantic table [chosen by this reporter] that is so beloved of farm-to-table restaurants, and even though the 30 300-year-old claims to be is extremely sick [and probably contageous], "with bloodshot eyes and nasal drip" and a sneeze that is, regrettably adorably, hurricane-like in force and fury, she is still wide-eyed and expressive and opinionated in a way that I would comment on even if she were a man. [WTF?] After we order—soup for her, fish tacos [in the dead of winter?] for me—we take a trip down not-boring lane: Her decision to forgo college or drama school so she could work at a casting agency and figure out how the sausage gets made? Not boring. Her breakout role on teen quality television, a bisexual vixen on The O. C.? Not boring. Her other breakout role, on grown-up television, a hardass (and, okay, fine: bisexual [she was also allergic to cats, but no one mentions that in the press]) doctor on House? Also not boring. The woman met an Italian princeling [better left to the imagination] at Burning Man and married him nine months later. This woman clearly had no interest in what was ordinary or expected, and what her parents' close friend Christopher Hitchens once characterized as her "headstrong" personality helped launch an acting career in which she was singular, inscrutable, and compulsively watchable. This part is great.

And then she went and got boring [had a shitload of fun], mostly by taking thankless two-dimensional [ not true, Tron was in 3D!] roles in big, noisy movies (Cowboys & Aliens, Tron: Legacy, something called Rush) that didn't need to be made and that nobody really saw. She also came dangerously close to following in the footsteps of, say, Sharon Stone or Kate Hudson: a somebody who remains somebody by dint of red carpets and cosmetics commercials [two badass ladies]. Although she doesn't come out and say it, I suspect she regrets making some of those movies. [I regret nothing, except this interview.] "I tried to follow the good material," she says by way of explanation, not apology, "but I didn't always do it. Because sometimes you need money, and sometimes you think it's good material but you haven't quite learned what actually works. And I was in my 20s! You don't really know who you are and you're trying out different identities, so maybe it was just a part of growing up." She pauses and looks away in thought [extremely drunk]. "I think I've been doing this for 13 years—12 years—but it actually feels like I started two years ago."

It began with Drinking Buddies [available on Netflix right now ], a low-budget boozy romantic comedy in which her unpredictability was leveraged to extremely charming effect. "That was the first time I felt I was in my element." And the further she gets from the kind of ingenuey roles she played in the big-budget movies, "the more interesting the roles get and the more fun the job is." She's been hitching herself more and more to smaller, independent movies for which she works for scale [peanut shells and ice cubes]. "The bullshit hierarchy of big movies doesn't help anyone. One actor having a mobile estate, triple-decker gym trailer—it just fosters a level of ego that is so damaging to our business." For her new movie, The Lazarus Effect (out today), a low-budget horror film from the guy who produced the Paranormal movies [and Whiplash], "We made it for so little money it was like being on a student porn set [similar craft service]. And it was a blast because we felt empowered. There was no executive saying, 'We need bouncing boobs in this scene….' " [Don't worry, we have one of those.]

She's popped up on Portlandia. She produced her first movie, a dark and stormy called Meadowland, which required her to deal with financing, unions, the whole nightmare [adventure]. (It'll likely [definitely] hit the festival circuit later this year.) There were the columns in Glamour and an infamous claim [joke] during a night of [private] monologues [unintended for public consumption until a sneaky reporter records them on her phone] sponsored by the magazine that she and her SNL alum fiancé, Jason Sudeikis, "have sex like Kenyan marathon runners." And she's gearing up to start work on a new dramatic series for HBO, produced by Martin Scorsese and Mick Jagger, about the rock scene in 1970s New York. She'll play the wife of a record executive, and "it's definitely the biggest deal of my career. I mean, Marty and Mick Jagger ?" [Yes. They are related.] (She hasn't worked up the steam to remind Jagger that they met before at one of her parents' D. C. dinner parties—she the precocious daughter of the host who wouldn't go to bed, he the midcareer rock star hanging out with Richard Holbrooke and Peter Jennings.)

We wrap up lunch, [she doesn't even pretend to reach for her wallet] and she's heading home to the newish brownstone she shares with Sudeikis and their nine-month-old son, Otis, and we swap stories about raising kids in the city. "One of the reasons we really want to raise him here is so he can have a normal upbringing," she says. "A lot of kids of celebrities, they can't help thinking they're more special than their peers, and it's not their fault they turn into these little assholes. We just want to surround Otis with as many interesting people as possible, and whatever he does with that, it's fine. He can become a juggler . He can become a mime ." [Full range of career possibilities.] Just so long as he listens to his mother, he should be fine. [I'm going to need this part blown up and framed.]

A version of this story appeared in the March 2015 issue.

Plus: A few of Olivia's Instagrams.

Beer Goggle Olivia Wilde Esquire

C Train, Baby Olivia Wilde Esquire

Au Naturel Olivia Wilde Esquire

I See You Olivia Wilde Esquire

Richard Dorment Richard Dorment is the editor-in-chief of Men’s Health.

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