Olivia Wilde: Fearless

The star on her journey to Meadowlands & her most challenging role yet

Movies Features Olivia Wilde
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Olivia Wilde isn’t intimidating. For all of you out there whose brows immediately furrowed, wait. Yes, she’s beautiful. Yes, she’s whip-smart. She’s also incredibly chill. Yes, chill. With every ounce of confidence and elegance she possesses comes immense relatability. She may a superstar, but she feels like the girl you cheated off of in math class, the one always with the lemonade stand down the street. She’s got something about her that’s welcoming, a passion that’s unobtrusive and still contagious. She’s a hustler. Especially when she speaks about her work on Meadowland, you sense a thirst, a desire to evolve, to learn. It’s no wonder her work on the film is her best yet.

It’s Columbus Day in New York and Wilde is lounged in a cherry red and navy patterned dress, leaning her head on the side of the couch. She and I admire the office where we’re doing the interview, the Manhattan skyline enveloping our conversation through the windows. Wilde has accomplished so much already in her career and Meadowland feels like she’s just begun a new chapter.

The drama is the directorial debut of lauded DP Reed Morano (Frozen River, The Skeleton Twins) and features Wilde as Sarah, a mother who has recently lost her son. Sarah and her husband Phil (Luke Wilson) cope with the disappearance of their child in vastly different ways, a journey that’s truly heartbreaking to witness. As Sarah is sucked deeper into a dream-like state of grief while balancing her job as a schoolteacher, Phil, a cop, finds solace in support groups and seeking who really kidnapped their son. The supporting cast also provides gravitas, with performances from Elisabeth Moss, Giovanni Ribisi, Juno Temple and John Leguizamo. Even young Ty Simpkins (Jurassic World) is effective as a student Sarah becomes fascinated with. Clearly, Morano is just as proficient with her actors as she is with her camera. Wilde not only stars, but also produced the project.

We haven’t seen anything like this from Wilde before either. Yes, she’s delivered a number of great performances in Her, Drinking Buddies, TRON:Legacy and recently in Rush, but Sarah crosses Wilde into new territory. Wilde’s already getting awards buzz. It all began at the Bowery Hotel in New York where Wilde and Morano first met to discuss the film. Wilde knew there were a number of other actresses up for the role, but was unyielding. After an audition at her own apartment with Reed and a bit more convincing, Wilde landed the role. Since then, Wilde and Morano don’t hesitate in proclaiming their ride-or-die partnership. It was meant to be. Wilde explains that it was more than just the challenging role that drew her to the project. It’s “a portrayal of a woman that I hadn’t seen and a portrayal of grief in a way that makes people feel less lonely,” Wilde says. “It encourages empathy with people that are going through something that they may not see as normal.” To her, it was a story that needed to be told.

But Sarah isn’t your typical do-this-to-win-an-Oscar role. We’re not rooting for her redemption the whole way through like many other notable female protagonists who have snagged golden statues and critical praise along the way. Sarah, Wilde points out, is pretty unlikeable. She’s a mourning mess, a slacking schoolteacher and commits a laundry list of other “bad” deeds throughout the movie—even if many of them are understandably motivated. Wilde wasn’t afraid to take on the anti-hero.

“The idea of likeability for women, in film or politics, is tricky. Is she likeable?” Wilde concedes that it keeps people from taking roles or financing movies. “That’s ridiculous! You have an ability to like everyone if perhaps you understand them a little bit.” In pre-production, Wilde recalls producers questioning the decision to make Sarah a pretty sucky school teacher, that audiences wouldn’t tune into a character that wasn’t empathetic. Wilde responded with assurance, “No. I think they’ll understand why someone in her position wouldn’t wake up excited to teach someone about poetry.” One of the comedic elements of the film is definitely the poetry Sarah chooses for her lessons—way over her students’ heads. She doesn’t seem to care.

It’s refreshing to hear Wilde speak so openly about taking on the anti-hero role, especially when it’s been male dominated over the past few years—most recently, with Steve Jobs and every show on Showtime. How did Wilde come to this place of security with herself and also with her career? How did she get to the point where she’s not afraid to sacrifice her Hollywood darling guise for gritty work?

Well, it turns out Wilde comes from a long line of journalists; family members who weren’t afraid to get their hands dirty, too. Her parents, Leslie and Andrew Cockburn are respected journalists and documentarians, working with 60 Minutes, PBS, NBC, CBS and a number of other platforms. They’ve uncovered powerful stories through various mediums from Soviet Military power to the Contra War and the Haitian military—the list goes on. Wilde reveals that what her family has “in common as journalists, documentarians and novelists is that they are storytellers.” Storytelling was a big part of Wilde’s childhood and acting was her way of “working for the family business,” she says.

If you haven’t noticed yet, Olivia Cockburn changed her name somewhere along the way. At 18, she decided to take on the name “Wilde” after the beloved playwright, Oscar Wilde. She’s a dual citizen in both the US and Ireland and wanted to honor her Irish roots and the revolutionary writer. A fellow theatre nerd myself, I inquire as to her favorite Oscar Wilde character. As it turns out, she did The Importance of Being Earnest in high school. She played Gwendolyn, to my surprise, which we joke is much more fun than Cecily. Wilde reveals, “It was the first time I felt truly thrilled being on stage.”

Wilde, like many other Hollywood hopefuls, headed to the West Coast at 18. She received a strong acting training in high school but still planned to go to Bard for college. Instead of heading into schooling right away, she hit L.A. and worked as a casting assistant. I wonder if Wilde endured the same painful journey of bad auditions like most young ladies in Los Angeles. She grins, leaning back on the couch and putting her hand through her brown locks. She’s preparing for quite a story—I can tell.

It was for a tampon commercial—the audition. There was the typical table of producers and directors that explained the scenario: Her roommate is having sex (of course) in the next room—where her tampons are (of course)! She was then told to crawl along the floor, picking up odd objects, from giant syringes to stuffed animals (in college?), along the way. “I got down on the ground, on the carpet, God awful dirty carpet, in an army crawl, she says.” Then—here’s the kicker—the producers and director started making simulated sex noises (of course). Wilde laughs, “It was like a weird Japanese game show!” She didn’t get the role—thankfully, right?—and didn’t go on another commercial audition after that.

Wilde also went through the madness that is pilot season, before the current climate when the majority of leading roles are offer-only. “These pilot auditions were bullshit. You’d have about three a day! I was really lucky to have that, but it was like being cattle!” Wilde’s candor about the often de-humanizing nature of the industry is revitalizing. The Hollywood machine can undeniably brainwash a young hopeful into self-deprecation. It’s awful. Wilde, though, has a sense of humor about it all. Her tales lack the depressing residue that many other blossoming career stories have. Wilde is aware of her fortune, though, continually stating how thankful she was that her plan to still go to college could be a lighthouse.

Even as talented as someone like Wilde may be, there’s also a dash of right-time-right-place that happens in any successful artist’s story. Wilde recognizes that luck was on her side. “I was experiencing a whole spectrum of the ingénue life of acting,” she says. With every shitty audition, there was one where she was being flown to Prague for James Bond. Although she studied for a summer at The Gaiety School of Acting, a part of The National Theatre School of Ireland, she admits, “I was convinced I would major in theatre and do a graduate program. It took a turn in a way I never expected.”

As much as Wilde’s early days seem without lack of severe challenges—at least to someone who researches her story—I gather there were many. Sitting across from her, even with her winged lashes and glossed lips gracefully sipping iced tea—she has a subtle toughness. A female who considers herself pretty tough and grown up around a slew of tough women—I recognize that this “toughness” rarely comes without the experiences that prompt someone to need to be tough—normally. When you say (or type) the word enough, it’s meaning becomes more elusive. I ask Wilde who supported her throughout her time alone in L.A. I’ve lived there and know it’s not as easy as it seems. Wilde credits her mother. “She always took my dreams seriously.” Wilde recalls her mother telling her, “You just have to read every play and see every play and keep reading and keep studying.” Only then, could Wilde be professional. “They filled me with a sense of confidence without filling my head with lies. I grew up believing it was within my grasp,” Wilde says about her parents. She stresses that it’s important to teach your child, “No matter what happens in terms of success, they’re a great person. I am grateful that I went through that and had a bunch of random weird jobs.”

Wilde is 31 now, is engaged (to partner Jason Sudekis) and has a son with him, adorable Otis—who’s just now a toddler. She’s far from tampon-commercial auditions at 18. I ask if she feels like she needed to be this age in order to take on a role like she has in Meadowland.

“I don’t think I could have done this before 27,” she says.

“Oh, great,” I reply, “I just turned 27 and I still don’t know what I’m doing with my life. “

“Twenty-seven is a really intense time in a woman’s life. There was a shift. For me, my life took a turn and I felt like I understood myself very clearly. I had gone through a very intense experience that made me very in touch with my emotions.” In 2010, Wilde went through a breakup with husband Tao Ruspoli, an Italian musician and filmmaker that she wed in 2003. The divorce was finalized in September of 2011. Wilde explains, “I wouldn’t go so far as to call it a tragedy, out of respect to people who experience real tragedies, but it was definitely a transformative experience. I think sometimes you have to fall apart to understand what you’re made of.”

It’s refreshing to hear her speak about an intense breakup with such a silver lining. It was a huge part of her evolution as a woman and subsequently an artist. I think anyone, male or female, wishes they could plop Wilde down across from their friends who are in that hurricane of a the breakup aftermath. She’d probably cheer them up—more than that carton of Ben and Jerry’s, for sure. Wilde elaborates on this emotional evolution by describing an experience screen testing for Stop Loss with Kimberly Pierce, who was “encouraging and cool.” Pierce saw Wilde do the scene and asked, “Has anyone ever done anything bad to you?” Wilde replied, “No, I’m really lucky.” “Whoa you’ve lived a charmed life,” Pierce responded. That moment was key in Wilde’s realization that actors get better the more they’ve been through. “I was raised by a very strong woman and in my early 20s I was tough and confident. Being tough and confident is great but as an artist that’s going to limit you,” Wilde says. She finds the positivity in that point in life where you have to be vulnerable; you have no choice but to “break down.”

Meadowland’s most powerful message mirrors Wilde’s well—without ever feeling like an agenda. It supports the grieving process without judgment. Like Wilde, it recognizes that breaking down is sometimes the only way to rebuild, and not just in the realm of parenting. “You don’t have to be a parent to understand loss or passion or pain. For younger people who can’t even imagine motherhood, it’s still relatable to see someone struggling with grief,” she says. Wilde is empathetic to the vast amount of youth struggling with depression and mental illness. Her character, Sarah, is bipolar and feels extremely isolated. “Young people sometimes don’t have the tools to work though that pain and understand that there’s light at the end of the tunnel. I think our film has an optimistic ending that it’s worth continuing to live.”

Not only was Wilde tackling this grief as her character every day on Meadowland, she was also putting herself in a personally challenging position throughout the shoot. Otis was four months when she shot the film. The idea of shooting a film about a mother losing her son, when Wilde just gave birth to her first, seems like an intense experience. “It was tough. For any mother, no matter what project you’re working on, you deal with a lot of guilt. Guilt management is a big part of parenting. You’re either letting down work, or you child, or partner,” She says. Wilde points out that Morano was also leaving her children at home. “That gave me the strength to show up every day with a good attitude. I never felt sorry for myself.” Wilde, again, finds the silver lining. “I was constantly faced with how lucky I was. I would come home to this beautiful baby. Poor Sarah, this is all that she wants—to come home to her child. It made me a more grateful person in general and it made me a more present and mindful parent,” she says.

Wilde’s passion for spreading uplifting and effective stories extends beyond just Meadowland. She’s been involved in a number of documentary shorts, which she produced. Baseball in the Time of Cholera explores the Cholera epidemic in Haiti and won the Best Documentary Short at Tribeca Film Festival in 2012. Body Team 12 also received the same award at Tribeca this past year, telling the story of the team responsible for collecting the deceased during the Ebola outbreak. “I think that documentaries are the most effective way to educate people about what’s happening in the world and create an emotional bond between cultures,” Wilde says, a new, different energy illuminating her. Wilde is hopeful about the state of documentary films, particularly shorts, recognizing that more are coming to fruition because of technology. “As a producer I’m able to help them get made and then help directors craft them into stories that will really resonate with audiences.”

Wilde also has her eye on directing. I bring up the short story she mentioned back in August that she’s adapting. Her body language says it all—she becomes a bit bashful, the timidity charming. “I hit a little bit of a snag with that! It’s hard to get something made! But Meadowland gave me the confidence to try anything. I’m excited because at this point, there’s nothing I’m scared of.”

As far-fetched as that statement sounds, something about it, coming from her, is utterly believable. Wilde may be beautiful, she may be whip-smart, but it’s her unquenched desire to illuminate the human experience that makes her fearless.