A Talk on the Wilde Side: Olivia Wilde’s Booksmart, Her New Home Behind the Camera, and Her Plans to Save the World

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A young mother whose eight-year-old son was abducted a year earlier awakens in the middle of the night.

She remembers her last day with him, how he was eating a cookie during a happy family road trip. She walks out to her car, puts her hands into the crevice of the back seat, and pulls out a crumb that the boy dropped there. She closes her eyes and puts it into her mouth with a rapturous intensity, savoring its essence, in holy communion with her lost child. There in the lonely shadows of a tomb-like parking garage we witness a parent coping with the most unbearable, devastating anguish any human being can experience. It’s an astonishing performance, as empathetic a portrayal of raw, visceral emotion and vulnerability as I’ve ever seen in cinema.

The film is Reed Morano’s Meadowland. I saw it four years ago at the Tribeca Film Festival, and it’s haunted me ever since. Watching that scene made my stomach churn with something akin to nausea. In an Ayahuasca-like reaction, I later felt a sense of disorienting wonder in the naked truth and humanity that such a portrayal of pain could elicit. I knew that if I ever had the chance to sit down with the remarkable artist who destroyed me with her searing, excruciatingly honest depiction of unfathomable, world-shattering grief, I would try to make it happen. 

Disappearing act: Wilde’s searing performance in Reed Morano’s Meadowland explores a parent’s worst nightmare. Image courtesy of Cinedigm

And as it happens, because good things sometimes come to those at MovieMaker who wait, on a warm Friday afternoon in March I found myself sitting in the bar at the Chateau Marmont in Hollywood, listening to Bob Dylan on the turntable, waiting for Olivia Wilde to arrive. 

If you’ve ever been to the Chateau, you know that it’s everything Hollywood is supposed to be, but rarely is. It’s on the Sunset strip, but just up the hill and well above the boulevard’s fray. It’s impossibly glamorous, but also understated and easy, with dark wood tones, antique iron chandeliers, and comfortable, well-worn furniture. It’s authentically old school cool and timelessly contemporary, too. And most importantly for my purposes, it’s open to the public and yet somehow still feels private and secluded. This grand old French castle with all its notorious history is an appropriately intimate place to have a conversation with a movie star of the people like Wilde. When I suggest it to her team, I’m not shocked when they say she loves the place, but I’m surprised to later learn that it’s actually been the Brooklyn resident’s Los Angeles home on a number of occasions, most recently during the better part of a year while she was in the city to make her directorial debut, Booksmart, her part salty subversive, part sweetly conventional and wholly original take on the teen comedy. 

She enters right on time, smiling and wearing a black “James Brown is Hip Hop” T-shirt (this is a woman who named her first-born after Otis Redding) and sits in an overstuffed chair next to mine. I give her a few copies of MM where she was quoted in our “Moviemakers of the Planet” feature several years ago, and where we profiled her fiancé, actor Jason Sudeikis. And because it was just her 35th birthday, I also hand her a fancy chocolate bar that I happened to have in my computer bag. “How did you know me so well?” she asks. “I can already tell this is going to be the best interview ever.”

Olivia Wilde sought to face her own motherhood fears by accepting the lead in Reed Morano’s Meadowland. Image courtesy of Cinedigm

She’s incredibly charming and, as I’ll find out over the next couple of hours, serious without ever seeming to take herself too seriously. And yes, let’s just get this out of the way, she is as gorgeous in person as she is on any screen. In particular, the eyes have it. Often referred as “feline,” that doesn’t really do them justice. They dance, they flash, they pierce, they smile, they do all the things that the eyes of a star at the vibrant height of her powers are inclined to do, but they do it with a kind of virtuosity. Equally striking is her warmth and wit, and the fact that although she’s unaffectedly down home in her speech and manner, the gleam from a lifetime of polish shines through. She’s preternaturally articulate, speaking in perfect paragraphs the way that the most magnetic people practiced in the fine art of personal communication (like her former boss on the campaign trail, Barack Obama) often do. Her voice is a bit deeper than one might expect, she laughs easily and often, and despite her New England boarding school background and part-time European upbringing, or perhaps because of it, her sense of humor is disarmingly irreverent. She has arrived in L.A. with her children (Otis, five, and daughter Daisy, two) in tow to do press and consult on the marketing efforts for Booksmart, which is being released on 2,500 screens (“3,000 if it opens well”) in May. You could say that Olivia Wilde is having “a moment.” Her new film just had its triumphant premiere, she’s starting a new production company, she’s the spokesperson for several social justice causes which mean so much to her, she’s happy in her personal life, and now she’s officially old enough to become president. Not that she wants that. But if she did, I definitely would not bet against her.

You could say that Olivia Wilde is having “a moment.” Her new film just had its triumphant premiere, she’s starting a new production company, she’s the spokesperson for several social justice causes which mean so much to her, she’s happy in her personal life, and now she’s officially old enough to become president. Not that she wants that. But if she did, I definitely would not bet against her. 

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