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Gucci top; Jennifer Fisher ear cuff and earrings.
Thomas Whiteside

Lilly Singh wants to throw up. The actress-comedian is hip-deep in prep for the September 16 premiere of her late-night NBC talk show, A Little Late With Lilly Singh, a debut that will make Singh the only woman hosting on a Big Four broadcast network.

“When my show got announced, people said to me, ‘Ohhh, two billion people are counting on you,’” Singh, 31, says of the pressure funneled her way, not just a result of her being a woman breaking into a man’s world but because she’s a bisexual Indian Canadian woman unleashing a much needed swell of diversity into an aggressively vanilla landscape. She’s also encountered fan after fan relying on her to detonate the glass ceiling. “I’m not viewing that pressure as negative, to be honest,” Singh says cheerfully. “I feel lucky to be in this position. I’m a minority in many, many ways, and I want to make sure that anyone, no matter where they are in the world, can relate and feel represented.”

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Marc Jacobs top and skirt.
Thomas Whiteside

Relatability has been her brand since 2010, when—combating depression—she began uploading self-effacing sketch-comedy videos to YouTube. “I was not in a good place back then. I was unsure. I didn’t know which types of people were good for me. I was upset at myself for being confused. Why don’t you know what you want to do in life? Your parents have paid thousands of dollars for this [psychology] degree!” Her channel, IISuperwomanII, has amassed nearly 15 million subscribers drawn to her balls-out humor and episodes with titles like “The Rules of Racism” and “When a Brown Girl Dates a White Boy.” Her book, How to Be a Bawse: A Guide to Conquering Life, was a 2017 New York Times best seller. In 2019, Singh was ranked 11th on Money’s list of richest YouTubers, with a reported $16 million net worth.

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Before her success, Singh kept a list of her idols. “Dwayne Johnson, Selena Gomez, Priyanka Chopra. People who I wanted to get their autograph one day. And now I’m in a position where, if I need advice, I call Dwayne,” she says, laughing. “I’d like to tell my former self, ‘Don’t be so stressed.’”

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Prada dress.
Thomas Whiteside

Her childhood self was, as she puts it, “a handful. I was a creative kid constantly doing weird things. I was a lot. I was also very obsessive. And that quality has followed me into my adult life.” Singh says she’s obsessively designing her talk show to reflect her media sensibilities, combining interviews with taped skits. “I’ve made it abundantly clear that I want to bring a great digital strategy and build community,” she explains. Her higher priority: “I want to make sure women and people of color are involved. I am constantly putting down my foot about that.” Above all, Singh plans to tip toward the positive. “When you watch my show, you will feel happiness. You turn on a little Lilly Singh, it’s going to be good times.” It’s a practice she carries into every aspect of her life. “I try to remember that everything I complain about, someone else is probably praying for.”

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This year she’s been actively pursuing spiritual growth—“I feel like I’m in a really good place”—but admits it took her a long time to find her center. “I vividly remember one day, I’d just gone to the White House. I met with Mrs. Obama, did a video with her, came home, went on Facebook, and saw one of my cousins got engaged. And I felt like crap. Like, Oh my God, I am such a failure; what am I even doing with my life? ” She exhales, continues. “The conditioning I’ve been raised with is if you’re not doing that linear path, then you’re straying too far. That’s something I’ve really had to unlearn because I am not made for that path.”

Singh clarifies she’s still very much a proud Indian woman. But she is more than the designation of any one culture or identity. She now tries to define herself by what is to come rather than what has always been. “When I make a decision as simple as what glasses I should get for my house, I think, Hmm, would my mom and dad like these? That’s insane. It’s a battle for me to get rid of those expectations. But I think that for the progression of any ideology, it needs to be challenged.”

Coming out was a challenge like no other. “When I tweeted about being bisexual, a lot of people told me it’s bad, that I shouldn’t do that, especially because I have fans in cultures around the world that might not support it. And I remember making the decision, like, well, eff it, you don’t get to have an opinion about who I am.” Plus, she’d let too much sun in to start yanking down the shades. “Loving myself was a very hard lesson. I want to love myself, but I also want to be myself.” Being herself has yet to steer Singh wrong. She delights in the absurdity of life and the goofiness of all humans, her creative output a glitter-bomb kaleidoscope of incisive silliness that is never unkind, never cheap. She invites us all in on the joke.

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Gucci top; Jennifer Fisher ear cuff and earrings.
Thomas Whiteside

“If my show or my video or my tweet can impact someone, that makes a big difference to me, because I know what it feels like to be uninspired and sad and then read something or watch something and have that flip a switch in my brain and be better for it.”

As for the future, Singh has, predictably, buoyant plans. She wants to buy “a big funhouse where all of my friends come to be creative, like the Willy Wonka factory.” She wants more dogs. To adopt kids. To tell stories that look like the world. To make herself proud, “because that’s the only person I can control.”

She’s thrilled to be part of this moment, excited people are speaking out against injustices. “My first vision board had things like ‘I would like to travel to Mexico,’” she recalls with a chuckle. “My life has surpassed anything I could have imagined.” And if that means she’s the tip of the spear in a fight for visibility for billions of people, Singh welcomes the challenge. “If after I die someone says, ‘I watched this girl, Lilly, and she inspired me to do X, Y, Z,’ what better legacy could you leave? The only lasting legacy you’ll ever have is the inspiration you leave behind. Thank you for listening to my TED Talk.”

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Louis Vuitton cape and dress; Simon G. Jewelry earrings.
Thomas Whiteside

This article originally appears in the October 2019 issue of Marie Claire. Read more about the women changing the future, in honor of our 25th anniversary, here.

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Photographer: Thomas Whiteside / Fashion Editor: Ryan Young / Hair: Bok-Hee at Forward Artists for Oribe / Makeup: Yumi Mori at Forward Artists for Chanel / Manicure: Dawn Sterling at Statement Artists for Dior / Production: Elise Connett at 143 Productions