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Lilly Singh vs. the Late-Night Jimmys

In a world of suits and cynicism, is there room for the YouTuber’s rainbow unicorn vibes?

Kwaidan Editions shirt, $950, at Marni pants, $950, at Irene Neuwirth rings, $5,390, at Photo: Djeneba Aduayom
Kwaidan Editions shirt, $950, at Marni pants, $950, at Irene Neuwirth rings, $5,390, at Photo: Djeneba Aduayom

Lilly Singh and I are crammed into a small dressing room at the West Hollywood soundstage of NBC’s A Little Late With Lilly Singh, where the newly minted late-night host is pitching me on the benefits of practical footwear. “Everything about me changes when I’m wearing heels versus sneakers,” she explains, pulling out a pair of Air Jordans that she recently paired with a powder-blue pantsuit, one of her favorite looks from the first few weeks of her new talk show. This afternoon, the 31-year-old Canadian is dressed in head-to-toe blue camo and white Nikes, and she carries herself with a loose, tomboyish stride — an energy that is offset by her curlicue lashes and shiny curtain of mermaid hair. She comes equipped with a tote-bag’s worth of spare vowels ready to throw into conversation at any moment, turning true into truuuuuuuuuuuue and yes into yaaaaaaasssss. “Like, in heels I’m a little bit more like this”— she says, drawing herself tall and placing her hands by her sides, like a drill sergeant. “And in sneakers I have more swaaaaaaaag, I have more fun, I run through the audience, I’m a little bit more myself,” she adds, crisscrossing her arms and bouncing up and down slightly, as if she’s perched on an invisible trampoline.

Singh leads me onto the main set, which features a cutout of Toronto’s CN Tower in the background, pictures of her favorite things on her desk (her dog, Scarbro, named after the Toronto suburb she grew up in; a carton of French fries), and a lucky loonie (Canadian dollar) coin hidden under her round throw rug. Filling one’s set with personal effects is part of the late-night ritual, but for Singh, it’s hard to tell where decoration ends and superstition begins. “I feel like me and the universe are really like THIS,” she explains, raising a hand to reveal one of her matching wrist tattoos (which read “Without Fear” and “Without Hate” in Gurmukhi) and crossing her fingers. “I’m on my third vision board, and most of the things on my vision boards come true,” she says. Some of the photos on her current vision board that came to life: Nicki Minaj (“I met her at the Met Gala a few months after that”), the Grammys (“I took over Alicia Keys’s social media backstage at the show”), and herself as a guest on a talk show … any talk show. “And now I sit in the other seat,” she says, grinning.

Balenciaga jacket, $2,290, pants, $1,190, shoes, $895, at 620 Madison Ave. Irene Neuwirth ring, $5,390, at Photo: Djeneba Aduayom

If you are the type of person who gets annoyed by things like vision boards and inspirational wrist tattoos, then Lilly Singh’s singular brand of rainbow-tinted optimism may not be your cup of loose-leaf tea. But it has worked on YouTube, where Singh has 14.9 million subscribers, 3 billion views, and a die-hard fan base of mostly young women that worship her like older ones do Oprah.  Now, in making Singh the first queer woman of color to host a late-night show, NBC is hoping it will be able to capitalize on that massive audience. It’s a big step for NBC’s late-night roster, which has exclusively been composed of men — but one that seems critical if the network wants to reach anyone else.  “Hiring her was a no-brainer,” says George Cheeks, who oversees NBC’s late-night programming.

On YouTube, Singh is an inspirational goofball who vlogs candidly about mental health, periods, pimples and poop, and makes teen-friendly sketches about relatable milestones, like going back to school and telling parents about a new boyfriend. Her wholesome, upbeat vibe skews decidedly more Lisa Frank than John Oliver; her production company is named Unicorn Island; her longtime nickname is “Superwoman” (also the name of her YouTube channel); and she regularly refers to herself as a bawse (see Singh’s 2017 best seller, How to Be a Bawse: A Guide To Conquering Life, and her special Smashbox lipstick color, Bawse). She generally steers clear of politics to focus on ideas like hustling hard, loving each other, and loving oneself. “I still believe in all of the temples of Unicorn Island and positivity, except now they’re probably expressed in a different way, because I’ve grown up a little bit. Now I’m very into mindfulness and meditation and communication and self-love,” she says.

When we meet a few weeks after her show’s mid-September premiere, Singh is still finding her TV voice. The show’s most popular videos so far — her opening monologue and introductory rap — got almost 1.5 million views, compared to the couple thousand her predecessor Carson Daly used to get on his videos, but a drop in the bucket compared with the nearly 33 million her most popular YouTube videos would get. Her monologues for the show generally revolve around personal anecdotes — such as her unsuccessful attempts at online dating — and are accompanied by games, chummy interviews, and sketch comedy. In one segment called “Lilly Singh Puts Problematic Brands on Blast,” she joked about recent racist gaffes from companies like Fitbit, then aired a parody ad for a Fitbit-like device called Step Buddy Color, “the very first fitness tracker made exclusively for people of color,” which can even track walks like “the Italian guido strut” and “the gang-member hippity-hop.” She is still trying to strike a balance between emphasizing her identity and being obscured by it. “I never want to be the person that pigeonholes herself into like, Oh, she’s just the brown bisexual woman,” she says. “When I first started my show, I knew that I wanted to be bold about who I was. Beyond that, I don’t feel the need to constantly bring it up. Now I’m just being myself.” So far, reviewers have found promise in Singh’s easy charisma, particularly her knack for connecting with the people she interviews, but she has faced skepticism about her tone; Vanity Fair’s Richard Lawson described some of the early writing as “corny, tame, as if the show is still pointed at the teenagers who first made Singh an online superstar nearly ten years ago.”

The challenge Singh faces now is figuring out how to cater both to subscribers actively seeking her brand of glitter-unicorn energy and to members of a more critical, less self-selecting TV-watching public who have grown accustomed to ingesting snarky news criticism with their nightly Ambien. To succeed, she needs to highlight those things that make her different from “the Jimmys”:  the unique vantage point that comes from being a queer woman of color in a sea of straight white men and that warm relatablity that catapulted her from her parent’s basement to global superstardom. But in a late-night landscape dominated by acerbic news commentary, with a battalion of SNL and Daily Show alums eviscerating/crushing/slamming/[insert over-the top gerund of choice here] our national political leaders on a nightly basis, is there room for Singh’s good vibes?

Marc Jacobs dress, $8,500, at Balenciaga shoes, $895, at 620 Madison Ave. Photo: Djeneba Aduayom

We head to the main set, where she leads me through her pre-show routine. She explains that she often shoots multiple episodes in a day, YouTuber style, unlike most of her late-night peers. “I give this person props and this person props” — pretending to fist-bump two imaginary crew members — “and then these doors open, and I enter,” she says, stepping in front of the camera and spreading her arms wide with a dramatic flourish. I take a seat on the slate-gray couch, and she conducts a mock interview, leaning in close and fixing me with an inviting smile. “How do you feel like this interview is going so far?” she asks. Singh-the-interviewer radiates warm, accepting energy, and even though I know we’re doing a bit, I feel at ease. “Are you getting what you want?” she asks encouragingly. “Do you feel like you could be getting more?”

Singh has spent most of her professional life figuring out what people want and trying to give it to them — albeit in a professional milieu her parents may not have envisaged for her.  Singh’s parents were born in India’s Punjabi region and met through an arranged marriage before immigrating to Scarborough, a suburb of Toronto, where her father ran a chain of gas stations. After completing her bachelor’s degree in psychology, working a soul-sucking office job to pay the bills, Singh fell into a deep depression. She couldn’t picture herself on a traditional career path, and she didn’t know what else to do. So she started making videos. “I didn’t start on YouTube to be rich and famous. I did it because I was so sad, clinically sad. And I didn’t know what I wanted to do in life,” she says. Gradually, Singh built a following, mostly with goofy, relatable sketch comedy that focused on the trials and tribulations of being a young South Asian woman living in Canada. Two of her most popular characters are her fictional mother and father, Paramjeet and Manjeet, performed in thick Indian accents, who show up regularly to do things like react to Nicki Minaj’s “Anaconda” video. “She wearing shoelace for underwear! She wearing shoelace in her bum, oh my God,” cries Singh-as-Manjeet, with a beard painted on.

As her channel started to find its voice, she asked her parents if she could forego grad school  and pursue YouTube full time. They reluctantly said yes, but only if she could get 100,000 subscribers in the next year; between January 2012 and January 2013, she jumped from 20,000 to 180,000 subscribers. As her following grew, her comedy started focusing less on her being a young South Asian woman and more on her simply being a young woman: 5 Things Guys Do That Girls Love (18 million views), How Girls Try On Clothes (12 million views), What Canadians Really Want to Say to Americans (15 million views), Types of Guys Your BFF Dates (11 million views), and so forth. She supplemented these sketches with daily vlogging, sharing her struggles with racism and bullying and depression and insecurity, and how she has fought to conquer them and you can too, all introduced with her standard upbeat greeting: “Whaddduuuup everyone, it’s your girl, Superwoman!”

Singh came up in a certain era of YouTube that looks quaint by today’s standards — before YouTube’s content moderators struggled to keep up with the amount of hate speech being uploaded on a daily basis. From 2011 through 2016, YouTube was on a push to promote what it saw as its most valuable original content creators, and Singh was consistently elevated.  “I think she created that space where teaming up with her was a cool thing to do,” says Kanwer Singh (no relation), a.k.a. Humble the Poet, Singh’s longtime collaborator, friend, and sometimes roommate. “If you wanted to reach a certain demographic, you work with YouTubers, and with Lilly Singh, you didn’t have to worry about anything being controversial. She’s the queen of relatability.”  In 2015, she was featured in a big-budget YouTube marketing campaign with fellow platform star Tyler Oakley. That year, she also did a 26-city worldwide stadium tour, funded by YouTube, and made a behind-the-scenes feature film about it, A Trip to Unicorn Island. From there, it was spon-con with Coca-Cola, Skittles, and Toyota, video team-ups with the likes of The Rock and Michelle Obama, a spate of TV and movie gigs, a memoir, and a brief mental-health break from YouTube in 2018 to pursue other opportunities. That included shooting a comedy pilot for NBC, co-starring Emily Ratajkowski; while the show ultimately didn’t go forward, Singh tested so well that NBC offered her the late-night gig instead.

The move to network TV was an easy choice for Singh, despite the fact that she was making more money on YouTube. Her ultimate goal, she says, is to do “the Dwayne Johnson” — to become a globally recognized brand with a vast range of creative projects. (The Rock has been Singh’s idol since high school, and now she considers him a friend and mentor.) “A lot of people have asked me this — Your YouTube videos have so many views, your TV show doesn’t have as many views, why would you go to traditional TV?” She says. “But I grew up with TV, I grew up with movie stars. I’m not of the generation that’s like: What’s TV? For me, it’s still very special to have a late-night show. I do think it’s due for an upgrade.”

At the same time, she’s aware that the medium that gave her a home for so many years is changing beneath her feet. Her YouTube channel has seen a decline in viewership in recent years, and at 31, she’s in many ways an elder stateswoman of the platform. “I had to make a very active choice that I personally can’t keep up with [the changes on] YouTube, I’m not willing to adjust to what is popular on YouTube, and I’ve stopped defining my success by that.” Is she worried about the day the teens surpass her? “I’ve kind of been feeling that already. There’s new apps all the time.” (For instance, she hasn’t been able to figure out TikTok.) While it seems counterintuitive to treat burnout by signing up for a daily talk show, there’s a unique kind of psychological pressure that comes with sharing every part of yourself online for the better part of a decade. “When I took my hiatus in 2018, I was spreading myself too thin. I had no personal life. It was work, work, work, work, work, and I had so many great things happening in my career and I was like, You are an unhappy person. So clearly this is not all it takes to be happy; there’s a part of this recipe that’s missing.”

While Singh will do social commentary on issues she cares about, she doesn’t plan to regularly engage with politics on her show. “I think right now there’s room for a show that doesn’t discuss politics, because it’s hard to escape,” Singh says. “And I’m also Canadian — me talking about American politics is just not authentic to me.” Yet despite her sworn refusal to engage with it, Singh has already had her first brush with 2019’s unpredictable political landscape. After photos of Canadian prime minister Justin Trudeau wearing brownface leaked, Singh and her team made the decision not to air a pretaped segment she had done with him days before. “It obviously did not feel great,” she says of Trudeau’s scandal. “I’m not saying that people shouldn’t have been hurt by it; it is a hurtful thing,” she continues. “But I also think that one of the downfalls of the internet is this whole idea of cancel culture. To expect humans to be perfect and never mess up would mean no one would ever learn or grow or evolve in any such way. And this is years and years and years ago. I didn’t know a lot of things were incorrect when I was in my teens.” (Trudeau was 29, the son of the former prime minister, and a schoolteacher at the time).

Singh herself has been accused of appropriating black and Indo-Caribbean culture on her channel because of her tendency to don a “blaccent” and make rap videos sporting chains and cornrows. A recent piece in Teen Vogue compared Singh to Awkwafina, who has also been criticized for appropriating black culture, and notes that “Lilly falls into a category of non-Black people of color in entertainment who have built massive followings often by mimicking Black culture and leaning heavily into Black stereotypes.”  Singh, who comes from the immigrant-rich cultural-melting-pot neighborhood of Scarborough in Toronto, doesn’t seem to accept the criticism. “My mentality that has leaked into everything I do is: This is who I am and this is what I am. Even with the way I speak, people have so many things to say. People make comments about, you know, I’m a little rough around the edges when I speak — it’s because of where I come from in Toronto. We’re a little bit ratchet, we don’t say ‘thing,’ we say ‘ting.’ It all goes back to ‘I am who I am.”

She has also made an appearance in the notes-app apology news cycle for comparing bath towels wrapped around Jessica Alba’s kids’ heads to Punjabi turbans. In this instance, when Singh realized the problematic nature of her joke, she took action. “As soon as it was brought to my attention, I immediately knew I wanted to apologize,” she says. “It was my first episode I taped, and I remember how nervous I was. And when I heard it back, it just didn’t sound how I wanted it to sound in my brain. I wanted to send an example of how I hope that mistakes are dealt with. I want to take ownership and genuinely apologize. There was no publicist telling me what to do. I was like: This is coming from me.”

After our studio tour, Singh drives me to her house in a shiny white Tesla SUV, bumping “Congratulations,” by Post Malone. Singh’s home is full of curated, on-brand personal touches that look great as the backdrop for a vlog but aren’t quite convincing as a place that someone would ever come to veg out and chill. The Toronto energy is strong: Bright-yellow walls sport whimsical custom artwork featuring Drake’s head juxtaposed against yet another CN tower, and her dog Scarbro’s bed is shaped like a giant Raptors hat. “It’s just so important to me to be around positive vibes and energy, which is why my house is yellow and bright,” she explains. “It’s solely because it makes me happy.”

“She’s the first person who taught me that your environment matters,” says Humble. “The first time I stayed over, she asked me what color towels I wanted. I said: What do I care? And she said: Try pink. And then you catch yourself in the bathroom mirror with the pink towel and it shoots off a couple of synapses in your brain. And you’re like: Oh, I get it, there’s a life beyond these boring gray towels that my mother bought us our whole lives.”

Now that she’s a TV host, Singh is trying to figure out how to set new boundaries with an audience that has grown used to seeing her spill every behind-the-scenes detail of her life. “I am drawing new lines,” she acknowledges. “I have become friends with a lot of people I was a fan of. Years ago, I might have blogged about, Oh my God, Dwayne [Johnson] tweeted me. I’m freaking out. Now if I go hang out with Dwayne, I’m probably less likely to talk about it. I’ve just entered a world where a level of privacy and professionalism needs to be respected.”

Another boundary she’s trying to negotiate is how much of her identity she wants to broadcast. While her YouTube content skewed safely PG-13 (she even refuses to curse), the new late-night forum leaves a door open for Singh to discuss more mature topics, like her sex life. Many of the promo materials, and Singh’s jokes on the show, have made a point of emphasizing her identity as bisexual; while she is able to joke breezily about her sexuality onscreen, it’s clear coming out was a big deal for her. “For me, coming out was a very confusing experience because it truly wasn’t me hiding a part of myself,” says Singh, who came out in February via an Instagram post. “People ask, How long did you know? And I’m like, I’m not really sure, and I think that’s because I grew up in such such a suppressive situation. I feel like in my culture, you’re very often encouraged to sweep things under the rug. So I never really let myself explore it any such way anyways. And I had to deal with people saying, You do so much business in India, you don’t want people in India to find out. It was partially if I’m honest, a big middle finger to this whole idea that we can’t talk about it.”

Singh has talked in her monologue about using the dating app Raya, so I ask how her first date with a woman went. “I haven’t actually gone on an actual physical date!” she confesses. “I’ve only messaged girls. I make jokes about it in monologues, but they’re not always true, to be honest.” Singh has never had much of a romantic life, which she chalks up to being a  workaholic. Now, she says, her new fame has created additional obstacles. “I’m a little bit insecure of someone dating me just because of my show,” she says. “I definitely would have to date someone who doesn’t know who I am, so I think I might just chill on that for a sec.”

While Singh has come a long way in regard to accepting herself and being open about who she is, this new level of success has its own set of insecurities — including the fear that people might still like her more for her outward-facing image than for who she is offscreen. Is she still relatable? What does relatability mean, anyway, in the context of global superstardom? Has she simply gotten so good at performing authenticity that there’s no longer any way to tell where the real Lilly ends and Lilly-the-performer begins — and does that matter, if she’s got the work ethic to back it up? Maybe she is simply one of those unicorns cut from the same cloth as her idol turned friend the Rock: just that nice, just that hard-working, just that poised for multiplatform world domination. “There really isn’t a different side of Lilly when she’s with her friends. I know some people assume she’s like this ‘on brand’ person and offstage she’s got a potty-mouth, but she doesn’t even swear in real life,” says Humble.

For now, Singh says, she is trying to enjoy the success she has built for herself. “I’ve just done way too many things in my life where when I look back at them, I can’t really remember if I had fun or not, and with the amount of work this job takes, it would be a shame if at the end of the day I was like: I’m sad. I can’t have that,” she says. “Of course some days I’m like, ‘Eff this,’ but then I wake up and come back the next day feeling optimistic all over again.”

Lilly Singh vs. the Late-Night Jimmys