Where does Lilly Singh go from here?
— There are two sticky notes clinging to the computer monitor in Lilly Singh’s home office. The first reads, “Appreciation over expectation.” The second, “Compassion over confusion.”
Singh, 35, is a Canadian YouTuber whose channel took off in the early 2010s. She didn’t expect to make it big goofing around under the display name Superwoman or playing her Indian immigrant parents in comedy sketches, but she gained a fan base of young brown girls who longed to see their experiences reflected online. Her charisma attracted a broader audience, earning her 14.5 million subscribers on the platform, and she rode that success into the mainstream, hosting events and booking minor acting roles.
Maybe that isn’t why her name rings a bell. In 2019, NBC hired her to host “A Little Late with Lilly Singh,” filling the 1:35 a.m. time slot originated eons ago by Bob Costas and held for more than 17 years by Carson Daly. She was the only woman hosting a late-night talk show on network television. “A Little Late” embraced that fact, also centering Singh’s queer and South Asian identity.
It was canceled after two seasons.
This left her wondering what went wrong. Was her comedy a bad fit for the network? Granted fewer resources than her late-night counterparts, had she been set up to fail? Did anyone even notice? After all, the show aired at 1:35 a.m. Maybe the lesson wasn’t about how to rise to the expectations of traditional media, but how to avoid the constraints altogether.
She’s moved on. So has NBC. (“Lilly’s unique talent and fresh perspective are what drew us to collaborate with her ... and we continue to be fans of both her and her work,” Katie Hockmeyer, NBC’s executive vice president of latenight programming, said in a statement. The network ceased to produce original content for Singh’s desolate time slot, which is now occupied by local programming.)
Whatever, right? Sustaining a career in the public eye takes determination and thick skin. One moves on as one must, but, like most YouTube stars who build brands off their personal identities, Singh receives criticism that can be quite cutting. A comment may not just point out that a joke didn’t land, but also assert that she herself has never once been funny.
She has come to expect intense feedback but wavers on how to handle it. Working in entertainment can feel “very heightened,” she says. “The highs are super high ... and the lows are, ‘Everyone in the world hates me.’” The talk show sparked those low feelings when it garnered middling reviews and subpar ratings, even in its wee-hours time slot. She reframed its cancellation as a sign to redirect her energy.
“I am stubborn by nature,” she reflects. “I feel like I have something to prove.”
Singh apologizes for the messy state of her office. There are a few papers strewn about in an otherwise immaculate room. The bookshelves are organized by color. A desk calendar is similarly coded by hue. Several copies of the self-help book she released last year, “Be a Triangle: How I Went From Being Lost to Getting My Life Into Shape,” rest in a neat stack at the corner of her desk.
She sits in front of a framed poster of a Hollywood Reporter magazine spread from a few years ago. It reads, “Lilly Singh seizes the night.” It hangs above the plaque she received from YouTube when she hit 10 million subscribers. Singh is proud of her achievements. She’s proud of her work ethic, describing her level of focus as “both amazing and bad,” in that she will spend endless hours on any given task until satisfied with the results.
These days, that includes projects put out under her Unicorn Island Productions banner (which produces the animated children’s series “The Mindful Adventures of Unicorn Island” and recently announced it was developing a new drama series starring “Bridgerton” actress Charithra Chandran) and gender-equality advocacy campaigns carried out by the company’s philanthropic arm.
“I really like a life where I have my toes dipped in a bunch of different things,” she says.
Singh was the second daughter born to a Punjabi Sikh immigrant family in the Scarborough district of Toronto. To some of her elders in India, she says, her birth was “a disappointment.” They had hoped for a boy who would carry on the family name and duties. She spent years challenging inherited notions of how a girl was supposed to behave.
She was told girls weren’t supposed to dance in public, for instance, but still captained a bhangra dance team at York University. After graduating in 2010, she worked a tedious job at a collections agency and found a creative outlet on YouTube. It took a few tries before she discovered her niche, gradually building a following with observational comedy directed at a second-generation South Asian audience.
It would be years before Singh posted videos under her own name. She started out as Superwoman, and in her earliest videos, such as “Official Guide to Brown Girls,” recruited friends to play other second-generation Indians and fictional versions of her parents. “The only reason I decided to start playing them myself was that, with the pace at which I was making videos and shooting, my friends were like, ‘We’re busy. We’re not coming to your house every day,’” she says.
Singh donned a wig and drew on a beard to play her bumbling father, and wore a dupatta over her hair to play her strict mother. The characters, while exaggerations of Indian immigrants that could veer into stereotype, helped her forge a sense of community with young people from similar families. Singh says she has “a complex with feeling seen,” which makes it all the more rewarding when others tell her they recognize themselves in her work. Making videos helped her navigate a period of depression.
Her parents hoped she would apply to graduate school. With fewer than 50,000 followers at the time, she countered with the idea of becoming a full-time YouTube creator. They agreed to give her a year to prove she could turn her hobby into a career.
This was when YouTube started to become “a more viable, actual business” by ramping up its advertising, according to Mark Bergen, author of “Like, Comment, Subscribe: Inside YouTube’s Chaotic Rise to World Domination.” In 2017, Forbes estimated Singh’s net worth at $10.5 million, ranking 10th on the magazine’s list of the world’s highest-paid YouTube stars.
First-generation YouTubers like Singh pioneered the now-ubiquitous approach of maintaining “this parasocial relationship with the audience,” Bergen said. “You treat them like a regular fixture in your life, and they do the same to you. That’s a core difference that has never really translated to TV.”
YouTube once seemed as though it could serve as a launchpad for Hollywood careers, according to Bergen, who likened this potential to “Saturday Night Live” stars landing major film and television roles. But as time went on, it became clear success in new media wouldn’t always translate.
Singh initially said no when NBC came to her with the idea of hosting a late-night show — which would require a great deal of her time and earn her less money than she was making on YouTube — but signed on after a member of her team pointed out that, as an Indian and bisexual host, she could help “break the mold of what the staple in traditional media is.”
“I’ve had the honor and the absolute tragedy of being the first in a lot of things,” she says.
Some of her apprehension toward late-night TV was warranted. She recalls experiencing a “steep learning curve,” going from a crew of five to 100. “I didn’t even know what 70 percent of those jobs were,” she adds. At the same time, she struggled to meet demands with the allocated resources. The budget required them to shoot 96 episodes of “A Little Late” over three months — or two to three episodes a day, according to Singh. She could only afford a fraction of the writers employed by comparable shows.
The first season was awkward. Singh’s monologues — often related to her identity on a more superficial level, whether about the difficulties of having long hair or being vegetarian — could seem forced and more generic than the video diaries that made her famous. She doesn’t fault her writers for this, noting that their schedule didn’t allow for much time to rewrite jokes, but admits that she would only personally watch 10 of the season’s nearly 100 episodes. “The other ones ... are not good,” she says. “We all know that.”
The loudest critics of “A Little Late” took issue with how often Singh brought up being a bisexual woman of color, but she says she was also scolded for not addressing her identity enough: “It’s just an impossible situation. The No. 1 culprit is that there isn’t enough representation . ... You have to be everything.” It stung even more when she received criticism from other YouTubers, because “that’s a community that has held me.”
She also felt she was tasked with appealing to viewers of Jimmy Fallon and Seth Meyers, whose talk shows aired before hers, while still expected to bring in a new audience. “Those are two goals that compete against each other,” she says. “I think there are actual greater systemic issues here about what it means when we bet on minorities and women. Is that an actual bet, or are you wasting everyone’s time?”
The second season of “A Little Late” aired during the pandemic and played more to her strengths. Recording monologues at home recalled the intimacy of her YouTube videos. Writer Romen Borsellino, who was hired for Singh’s second season, said the staff aimed to “build a show around her style, rather than trying to fit her into this preexisting (latenight) structure.” They introduced a segment called “Lilly’s Rants,” in which she delivered directly to the camera the sort of pointed cultural commentary she did in, say, “Official Guide to Brown Girls.” Borsellino, who previously worked for the Obama administration, collaborated with Singh on political segments as well.
“She expanded the topics ... to things that had previously been outside of her wheelhouse,” Borsellino said. “I think the approach describes Lilly in a lot of ways, and her willingness to collaborate.”
Though Singh’s first season dropped less than 10 percent in ratings from Daly’s final year in the 1:35 slot, Nielsen reported that the second season of “A Little Late” fell another 27 percent. Singh says she feels “a little bit like that show never got a fair chance. It is a bit of an asterisk in my life, where if I have a little bit of doubt, I’m like, ‘What if I did this? What if this happened? What if I do that?’ But ... the universe taught me everything I needed to learn, to do something greater.”
The two self-help books Singh has published “are part of who I am,” she states. The first — 2017’s “How to Be a Bawse: A Guide to Conquering Life” — is a product of millennial hustle culture. The second, “Be a Triangle,” presents a more balanced approach to seeking fulfillment in a career. “This book is, why does any of that matter and what does any of that mean? Because at the end of the day, that can’t be who you are. You can’t be your work.”
What does it do to someone to have navigated young adulthood on such a prominent platform? She grapples with the growing recognition that many of her biggest critics tend to be other South Asian people, but tries to remind herself that her most loyal fans are, too: “Every time I’m arguing with (someone online), there’s another brown girl being like, ‘Ignore him. You raised me. I love you.’ Why am I ignoring that?”