Lilly Singh: From YouTube Superwoman to NBC Late Night TV Trailblazer
Alexandra Gavillet

Lilly Singh: From YouTube Superwoman to NBC Late Night TV Trailblazer

An online star with 15 million subscribers dives into the white-hot center (emphasis on white) of broadcast television with 'A Little Late' as the first openly bisexual woman of color to sit in a talk show host’s chair: "I’m very much all or nothing."

When Lilly Singh runs a pitch meeting, she comes bearing gifts. "Live your best life in the office — you don't have to wear shoes!" she announces to the writers she's assembled on this scorching August afternoon in a drab conference room off Melrose Avenue in Hollywood, where they'll be discussing ideas for her new NBC late night show, A Little Late, which premieres Sept. 16. She proceeds to toss out pairs of fluffy white unicorn slippers.

Singh, dressed in a knee-length white vest and matching saddle shoes, her long raven hair dangling in a ponytail, is something of a unicorn herself. Not only is she one of the few females to brave broadcast TV's late night airwaves since Joan Rivers famously flamed out on Fox more than 30 years ago, she's also the first openly bisexual woman of color to sit in a host's chair. Perhaps as significantly, she's the first internet-bred star in broadcast late night, too.

While her name and face might not be familiar to the traditionally older demographic that tunes in to late night, Singh, 30, is hardly new to the post-broadcast generation of viewers who wouldn't know a Jimmy from a Seth or a Stephen, let alone a Carson (of Last Call With Carson Daly, whose NBC time slot she's taking over). For the past nine years, she's been building her own uniquely personal, extraordinarily successful brand on YouTube, where nearly 15 million fans know her as Superwoman (the name of her channel) and consider her something between a star and a best friend. Her 2013 post in which she poked fun at women's getting-ready rituals has been viewed nearly 29 million times. Another, the music video Voices in 2016, has grabbed 9.5 million. And an interview with Michelle Obama has 2.3 million. Even Singh's more mundane life updates attract huge numbers, like the 2018 Instagram post in which she introduced the world to her new puppy. It drew more than 700,000 likes (or roughly the same number of people who tuned in to Daly's Last Call before he called it quits, after 17 years, in May).

Internet stars have (sort of) crossed over before. YouTube comic Miranda Sings landed a Netflix series. Grace Helbig parlayed her awkward humor into a talk show on E! (after Chelsea Handler bolted for Netflix). But none has ventured this deeply into the white-hot (emphasis on white) center of mainstream entertainment. And late night TV — even at the ungodly starting time of 1:35 a.m. — is an altogether different league with an altogether different audience and different demands. So, naturally, Superwoman is feeling the pressure these days. "There's a small part of me that's like, 'Is everyone going to like this?' " she acknowledges after she's done throwing footwear at the writers (some of them later even put on the slippers). "That's obviously a fear. But I'm going to do what I've always done, which is make something that I think is good, that is authentic to me. That's what has gotten me my success thus far."

***

Singh inherited her hustle from her father, who after leaving India's Punjab for Canada with her mother in the 1970s tried out furniture sales and working security before he opened a slew of gas stations when she was at university. "I've imitated him quite a bit," she acknowledges, rattling off all the jobs she has held down — collection agent, drive-thru cashier at Canadian fast food chain Harvey's, camera saleswoman, dance instructor.

Her adolescent years in the Toronto suburbs were a picture of normalcy: While her parents were hard at work creating opportunities for Singh and her older sister, Tina, she was listening to rap music in her bedroom, idolizing Dwayne "The Rock" Johnson and dreaming of a career in entertainment. By 2010, she was a senior at York University still living with her parents and wondering what she'd do with a degree in psychology, and she was struggling with depression.

That's when Singh discovered YouTube. There was AKTV, a brown kid from Canada just like her, talking about Indian stereotypes and freestyle rapping from his bedroom, and Helbig, uploading daily dispatches about life as a post-grad. For a girl with big dreams who was feeling utterly alone, those videos became a lifeline. Soon she worked up the courage to create a channel — the name Superwoman came from her first MSN Messenger screen name, cribbed from the early 2000s rap song by Missy Elliott protege Lil' Mo — and posted a video of her own, a spoken-word poem that she later took down because it was "so crazy." Amazingly, it got 70 views. "I was like, 'Whoa, I am famous,' " says Singh. "It boggled my mind. How did these people find this video? Who were they and why were they watching?"

It was enough positive reinforcement that Singh kept going, immediately throwing herself into multiple posts a week despite knowing nothing about camera angles, lighting or video editing. She was enjoying a scoop of ice cream with a friend a few months later when her phone began to blow up. Earlier in the day she had released "Official Guide to Brown Girls," an 11-minute comedy bit about the quirks of Indian women and the men who woo them, and it was rocketing to 10,000 views. "My phone was going bing, bing, bing," she says. "After that, I turned off the notifications."

Singh's parents knew nothing about their daughter's (very public) secret hobby until family members starting calling and asking, "Is your daughter, like, doing things on the internet?" Although they would have preferred that she get her master's, Singh convinced them to give her a year to focus on YouTube. She invested more time (and money, saving up for a $600 professional camera) and began collaborating with other YouTubers. Soon, her profile started to grow. Graduate school was shelved indefinitely.

Initially, the paychecks were small — her first invoice from YouTube, which splits ad revenue with channel partners, was about $18 — so Singh made ends meet by emceeing events around Toronto. She didn't hit 1 million subscribers, a magic number that equals success within the YouTube community, until 2013. That's when her channel began to take off, amassing the next million in a matter of months.

"She has never gone viral. She has never had that 'big break.' She never got discovered by that celebrity," says Kanwer Singh, a fellow Torontonian (no relation) who came up on YouTube under the pseudonym Humble the Poet around the same time that Superwoman was making her name. Instead, he describes Singh's appeal as "a mixture of honesty and intelligence" that strikes a chord with fans around the world who relate to her frank and open discussions about mental health and the way she describes her own coping mechanisms — like escaping in her mind to a happy place called Unicorn Island when she's feeling sad. "It was clear that she had a message that really resonated with people," says manager Sarah Weichel, who in 2013 was shown one of Singh's videos and flew her to Los Angeles for a meeting. "I'll never forget, the first thing she said to me was that she wanted world domination. That was the thing that really drew me to her, how ambitious she was."

In 2015, at 26, Singh finally moved out of her parents' house and to L.A., where she rented her first apartment in Mid-City (she dubbed it the "Lillypad") and really got down to business. A 27-stop world tour, a feature documentary, cameos in films like Bad Moms and brand sponsorships from Smashbox, Skittles and Coke followed. The girl who once balked at spending $600 on equipment was now raking in five-figure brand deals (those now can draw upward of $1 million, contributing to a total income said to be in the high-seven figures annually). Onetime idols like Priyanka Chopra and Dwayne Johnson (with whom she struck up a friendship after they met at the 2015 MTV Movie Awards) also began to pop up in her videos. "I've seen Lilly just plow through her vision boards," says Kanwer Singh. "You can imagine almost 10 years ago hearing her say, 'I'm going to meet The Rock one day.' And the next thing you know, not only are we at a movie premiere with him but he's mentoring her."

Still, there came a moment, just last year, when Singh realized that her vision board needed an overhaul. Although her career was going exactly as planned — she was making strides as an actress, having completed a turn as a vlogger in HBO's Fahrenheit 451 adaptation, and had set up a shingle, Unicorn Island Productions, to develop her own slate of creative vehicles — she was totally, utterly miserable.

***

"I came home one day and I remember lying on my kitchen floor and just crying," Singh confides over glasses of orange slice-infused water at the Hollywood condo she purchased in 2016 (she's decorated it in aggressively happy colors, with lemon-yellow walls in the living room and raspberry-pink in the bedroom) and where she lives with her now-full-grown poodle mix, Scarbro, named for the town where Singh was raised. "I turned into such a machine. I was feeling that I was completely losing what it means to be human."

After eight years of perfecting the business of YouTube, she'd let it consume her. At the height of her output, she was producing as many as nine videos a week, not to mention dozens of tweets, Instagram posts and other social missives. Afraid that if she took a day off the YouTube recommendation algorithm would leave her behind and a subscriber backslide would begin, she barely let herself take a vacation. She was preaching balance and self-love to her fans, yet she'd stopped her own therapy, given up journaling and was barely reaching out to friends.

Then, on Nov. 12, she posted one of her most raw, vulnerable videos yet. In "I'll see you soon …" — which quickly racked up more than 2 million views, though that was hardly the goal — Singh revealed that she'd be taking an indefinite break from YouTube. "I'm going to be real with you all, I am mentally, physically, emotionally and spiritually exhausted," she told fans, adding that, lately, "I haven't been super happy with a lot of the content I've created."

Indefinite, however, is a squishy time frame. Within a month, Singh was back. During that downtime, she found a therapist, adopted meditation and called her friends. Singh also had been grappling less publicly with the decision to come out as bisexual. "It's not that I had this big secret," she explains, shifting in her seat and scanning the living room for Scarbro, who is too busy chewing on a stuffed unicorn in the corner to offer much support. "Because of the culture I was raised in, I never actually allowed myself to figure things out. Moving to L.A., I was exposed to so many different types of people, and I think that probably opened up my horizons."

She gave herself a deadline, her 30th birthday, to come out to her family and friends, but it took another five months before she would share the news with her fans, via a casual tweet identifying herself as "female, coloured and bisexual." She's now trying out dating apps ("They're scary") but says fans shouldn't expect to hear much about her romantic partners: "I've signed up for this life, but not everyone has."

Singh had been warned that her business might take a hit, especially in more conservative countries where she'd developed a fan base, but aside from some Twitter vitriol, the reaction was largely positive. "The very next meet-and-greet that I did after coming out was in India, and I would say 50 percent of people in that line came out to me," she says. "To me, that is success."

***

Last summer, while Singh was preparing to focus more on herself, executives at NBC also had begun to focus in on her as they worked out a plan with Daly to turn the lights out on Last Call, which by that point had been boiled down to a potpourri of prepackaged segments.

NBC could have stopped programming the time slot (no other broadcast network airs a third late night show) but executives saw an opportunity to experiment and create what NBC Entertainment co-chairman George Cheeks calls "a creative playground." They put out a call for talent, and John Irwin, who has been producing specials for NBC since working on Late Night With Conan O'Brien in the 1990s, suggested they take a look at Singh; he'd been impressed by her ability to switch between wacky sketches and serious interviews with the likes of Obama, Bill Gates and Charlize Theron. "That's the hardest part of the job, being able to sit down with a guest and make it feel natural and comfortable," says Irwin.

Singh was already familiar to NBC from a shelved pilot by Black-ish creator Kenya Barris (Bright Futures, about a bunch of awkward 20-somethings). So Irwin placed a call to her agents at WME to feel out if she'd be interested in the gig, then flew to 30 Rock, where the only other name executives had been seriously considering was onetime swimsuit model (and current cookbook author) Chrissy Teigen, who had already passed.

From NBC's point of view, hiring someone with Singh's digital savvy made sense. Not only could she bring a much-needed dose of diversity to the heavily white, entirely male broadcast late night landscape, she also could potentially connect with young audiences that increasingly are abandoning broadcast for YouTube and Netflix. Besides, much of the battle over late night dominance has shifted from morning-after Nielsen ratings to share of the next day's social media buzz. Who better to create sketches that go viral than a star who grew up on the internet? "We felt like she had the kind of voice that we could build a show around," says Cheeks. "We weren't even sure whether she'd be interested, but the moment we sat down, it became clear her talent transcends whatever platform she's on."

Singh initially wasn't interested. She was already burned out by her existing workload, and through her production shingle, she was starting to line up projects with producers like Barris and Paul Feig that, if they moved forward, would offer the opportunity to do more acting. "The doubt wasn't whether this was exciting for me, it was whether this was a puzzle piece that would fit well in my existing life," she says. But after NBC came back to her, she sought the advice of pal Johnson ("You can create your own path," he counseled) and Hasan Minhaj, who in the midst of prepping his own Netflix talk show, Patriot Act, told her that late night would only raise her profile, not pigeonhole her. "Don't think of it as a stepping stone," he recalls telling her. "If it works, great, but if it doesn't you still have millions around the world you can communicate with."

In the end, her negotiations with NBC boiled down to her desire to give late night her all while also continuing to make videos for YouTube and pursue other off-network opportunities. NBC ultimately agreed to retain only talk-show exclusivity and to let her block-shoot the 96-episode first season during the fall, which would free her to focus on other projects the rest of the year. Singh's personal YouTube presence, meanwhile, is seen by the network as a valuable marketing tool to help build an audience for A Little Late. "I didn't want to sign up for it and then be like, 'I can only make a little time for it,' " she says. "I'm very much all or nothing." So she went all in.

On March 14, Singh flew to New York to announce A Little Late on The Tonight Show alongside new network colleague Jimmy Fallon. "Your girl is getting her own NBC late night show — and to clarify, it's not Jimmy's slot," she joked with Fallon before Late Night's Seth Meyers turned up and surprised her onstage with champagne. She's been texting Fallon ever since and has found other comedians equally welcoming. Amy Schumer offered writer suggestions and, when Singh ran into Trevor Noah at the Met Gala this spring, he gave her tips on how to survive her first year.

In the meantime, there have been hundreds of decisions to make. Does she want a desk? "Yes. It's actually a very functional thing," she explains. "You can store things behind it and you feel more comfortable because you don't have to sit pretty." Will she do a monologue? Absolutely. In fact, she has to write 25 of them before she even begins shooting in early September. There also will be preproduced comedy sketches and interviews.

One of the biggest decisions, of course, has been assembling her team of writers, a particularly daunting task for somebody who has spent years scripting and delivering her own lines from her living room. In addition to exec producers including Irwin and Polly Auritt, the head of development at Singh's shingle, she has appointed longtime reality producer Aliyah Silverstein (The Writers' Room, Hollywood Game Night) as her showrunner. The rest of the room is made up of veterans of The Late Late Show With James Corden, Kroll Show, Alternatino and The Tonight Show. "I want them to feel comfortable bringing their point of view because that's why they're in the room," she says of the half-female, predominantly diverse team. She's also learning the not-so-subtle art of encouragement; she brings a money gun filled with fake $100 bills and sprays the room whenever she hears a joke she likes.

Not at all surprisingly, Singh's been hands-on when it comes to her show's social strategy, including the upcoming launch of its YouTube channel, where clips from the previous night's episode will live alongside web-only sketches. "I think of the show as launching at 1:30 and then it has a life for the next 24 hours," she explains. NBC — which is planning a primetime special to boost awareness for the show following the Sept. 18 finale of America's Got Talent — is cool with that plan: "We will be totally fine if the audience discovers A Little Late on YouTube versus NBC," says Cheeks. Digital ads may still get pennies compared with TV dollars, but the opportunity to sell deeper sponsorships could prove lucrative. Already, NBC has received interest from brands that want to be in business with Singh, and Starbucks has signed on as an official launch partner.

While the block shooting schedule — two episodes a day in front of a studio audience for three months — means that A Little Late's four episodes a week run the risk of feeling stale in an era when the news cycle operates at the speed of a presidential tweet, the hope is that a show focused more on comedy than current affairs will be a refreshing break. "There's a million places to get that information," says Irwin. "Our goal is to do half an hour of comedy. We're going to stay away from politics. Her stuff is going to be a little more personal, a little more based in her experiences."

***

Back in the conference room in Hollywood — which Singh has made just a smidge less drab by hanging framed prints of cheesy-cheery sayings ("Stop tweeting boring shit," and, "Nothing good comes from hitting Reply All") — her pitch meeting with the writers is winding down. She has more ideas she'd like to discuss, but she's also got segment producers to interview and set designs to look over.

The whole process of starting a new talk show has forced her to think a lot about the version of herself that she wants to put out in the world. And even though there are millions of people who already feel like they know her, she hopes that when she walks out onstage Sept. 16, they'll meet someone new, too. "When I created my YouTube channel, I was, like, call me Superwoman," Singh says just a few days before she'll change her social media handles to her first name (her YouTube channel remains unchanged). "More and more, I would like to call myself Lilly."

***

Superwoman to Superbrand

PHILANTHROPY

Singh says she has hired someone to run her #GirlLove campaign to support women's education, which fundraises through jewelry sales (over 15,000 bracelets have been sold this year) and boosts awareness through interviews with luminaries like Michelle Obama.

PUBLISHING

How to Be a Bawse, a hybrid memoir and self-help guide, has sold 85,000 copies in the U.S. since 2017, per the NPD Group, and hit the New York Times Best Sellers list.

FILM AND TV

"We can give a platform to people who might not have one," says head of development Polly Auritt of Unicorn Island Productions, which has 20 projects lined up with partners like Kenya Barris, Paul Feig, Nisha Ganatra and Larry Wilmore.

This story first appeared in the Aug. 21 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.