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YouTube Star Lilly Singh (aka Superwoman) on Her New Documentary

By Julia Felsenthal

Lilly Singh, aka Superwoman, aka the 27-year-old Canadian singer, comedian, and YouTuber with nearly 8 million followers and over a billion views, talks exceptionally fast. So fast that when I try to transcribe the interview I did with her over lunch last week, it takes an entire day to get through an hour of recording.

Of course, anyone familiar with her manic YouTube persona already knows that Singh can fit more into the hours of the day than the average human. Every Monday and Thursday, she posts a sharply observed scripted comedy video that she writes, directs, shoots, edits, and stars in, often playing multiple characters in full makeup and costume. (Among her most popular are “How Girls Get Ready” and “Shit Punjabi Mothers Say,” though I’m partial to “How My Mother Stole Christmas,” for which she wrangled Seth Rogan and James Franco to play Santa and an elf.) Every morning she dutifully posts a vlog narrating her day and her emotional status for her mega-fans, who call themselves “Team Super,” though there’s also a subculture of devotees who refer to themselves as “The Lillycorns.” Last year, she did all this while on a two-and-a-half-month, 27-city, 31-show world tour, during which she performed a set that had her rapping, dancing, doing stand-up, and delivering motivational speeches to packed auditoriums of shrieking, weeping, mostly tween-age girls.

"My friends don’t understand," Singh says when we meet for lunch at an out-of-the-way Austrian restaurant in Tribeca. "They’re like: 'What do you do for a living?'" In person the Toronto-raised, L.A.-based YouTuber is movie-star pretty and nearly as animated as she is in her videos. Like her Internet persona, she has a tendency to refer to herself in the third person. Unlike her Internet persona, she’s traded in Superwoman’s signature tomboyish jeans and tees for a very feminine printed dress and fringed stiletto booties.

"I always feel like I push myself too hard," Singh says, telling a story about landing in the hospital with severe dehydration and exhaustion during a run of six consecutive shows in India. “But I don’t necessarily think that’s always a bad thing. I think to achieve things you have to push yourself too hard. When I was younger, I had this fairy tale that you can have the eight hours of sleep and be a healthy, balanced person and still achieve your goals. The reality is, that hasn’t always been the case."

Luckily, all that hard work is totally on brand, as is everything in Singh’s life, it seems. "On an average day, I will spend 90 percent of my waking moments working on Superwoman," she says. "I'm a huge workaholic. My hobby is Superwoman." While the videos she posts on her main channel tend to be straight-up humor-driven — Amy Schumer, Melissa McCarthy, and Rebel Wilson are comedic heroes — her overall vibe is far more wholesome and motivational, a synergy that strikes me as uniquely millennial. Hustling to achieve your goals is a major theme of Singh’s vlog channel; of her stage show, titled A Trip to Unicorn Island; and of the same-name documentary that she released yesterday on YouTube Red, the official reason for our meeting.

"Unicorn Island is the synonym for my happy place," she explains. "It's a really beautiful message: that happiness is one of the hardest things you’ll ever fight for, but it's the only thing worth fighting for." The idea derives from her oft-told YouTube origin story: In 2010, Singh, the daughter of Indian immigrants, was getting her bachelor’s in psychology with an eye toward a master’s and a career in counseling. Then she realized how unexcited she was about that path, fell into a deep depression, and emerged only once she discovered YouTube and began to post her own videos, produced in her bedroom with her MacBook webcam. The views rolled in, and she quickly got hooked on the format and on spreading her newfound positivity and good humor, a process that conveniently also bolstered her own mental health.

Like its subject, Singh's documentary, which follows her through the arduous process of conceiving and implementing her world tour, does double duty. “It’s a story of happiness, of a sad person deciding to be happy and sharing that message with the world,” she explains. “And then for people who have no idea about YouTube, it’s the story of how the hell somebody who makes videos in her room can go on a world tour that gets sold out over and over and over again. How does that make sense?” she asks, laughing. Well, how does it? “Because the world is changing in scary-rapid ways, and I was lucky enough to keep up with it,” she says, then adds, forebodingly: “I think there are a lot of people who were not. I think the film will be eye opening in a lot of ways.”

The world may be changing, but Singh’s movie reflects a funny tension between new media and old. The project is predicated on the notion that the people who adore Singh’s easily digestible, bite-size YouTube videos will be equally interested in an 80-minute, feature-length documentary (albeit one released on the Web). And the tour reflects Singh’s desire to translate her Internet shtick into a more traditional format, in this case, the old-school live variety show. In the future, she tells me, she’d like to do TV, perhaps a sitcom like New Girl.

The film is also about the joy of putting a face to the teeming anonymous masses of her Internet fan base. “In the simplest way, it really brings to light the fact that the Internet works,” says Singh, a self-proclaimed “geek” about analytics. “Sometimes you’re sitting at home on the computer, and you forget that these numbers and names are actual people until you’re there, you’re speaking to them, and they’re speaking a different language, but somehow you have this connection. It’s crazy if you think about it.”

Crazy indeed. For all her hard work, the insane luck of her career isn’t lost on her. “You know how you have dreams as a kid? I’m experiencing things I never even dreamed of. Going on Fallon”—which she did a couple weeks ago—“that wasn’t even in my realm of thought.” Later she tells me another story, about being on tour in Dubai and finding 500 roses in her dressing room, sent by an overzealous businessman. “Dubai is crazy!” she remembers. “Dubai is very rich.”

She keeps a vision board above her bed that’s plastered with pictures of her idols, like The Rock and Selena Gomez, both of whom have appeared on her channel; an image of L.A., where she recently moved; and one of the Streamys, where she took home the Best First Person Series award last September. “It’s eerie how many things have come true.”

The bread and butter of Singh’s operation is her comedy channel, based on her keen observations about experiences that are broadly relatable: the convoluted thought process girls go through when texting their boyfriends, say, or what it would look like if men got their period. Where, I ask, in her new Tonight Show–appearing, celebrity-courting, world-touring, kissed-by-a-rose life does she find the time to have the mundane experiences that spawn those videos? “That’s a really good question,” she says. “Sometimes I’m having conversations with my friends, and I feel like they can’t relate to me anymore. I’m like, ‘Oh, my god, let me tell you about my experience on Fallon!’ And they’ll be like, ‘Oh, my god, let me tell you about my trip to the mall!’ It sometimes feels lonely.”

But the ideas are everywhere. As if to prove her point, she picks up her phone. “I just thought of a video, so I’m going to jot it down really quick. When you said, ‘observations,’ I was like, ‘Oh yeah, I really do observe things!’ Like, oh, my god: Do I sit weird?” She flops around a bit on the deep banquette to demonstrate. “I should make a video on how girls sit. I’m always thinking: Is my dress up? Are my legs okay? Am I getting the jean crotch going on?”

She stares at her phone and types but keeps talking, a mile a minute. “I just think it’s a thing, and now I’m going to make a video about it. Am I slouching? There are a lot of things going through my brain right now. I was just sitting on my hair. That’s totally part of the video!”

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Photo Credit: Gabriel Olsen/FilmMagic/Getty Images