Lilly Singh’s Late-Night Challenge

The internet star snagged an NBC show because of her YouTube charm, but she’s still finding her footing in a traditional arena.

The Canadian YouTube personality was hired to shake up the white-male-dominated late-night landscape. (Scott Angelheart / NBC)

Go ahead, label Lilly Singh an outsider. The newest addition to late night knows she’s a television rarity—a “unicorn,” as she calls herself. “The media has mentioned I’m a bisexual woman of color so much I feel like I need to change my name,” Singh quipped during the opening monologue of her new show, A Little Late With Lilly Singh. At the time, she laughed off the joke with a graphic of a faux logo. But Singh, the first openly queer woman of color to have her own late-night series, walks a tightrope: She has to challenge the rules and play by them at the same time.

The Canadian YouTube personality was hired to shake up the white-male-dominated late-night landscape, and being broadcast on a Big Four network means catering to a widespread audience. No wonder her introductory rap ends with a question:

I’m about to bring a new POV and make some noise
Might push your buttons, make you turn around like on
The Voice
Ain’t playing soccer, but I’m about to kick it with the boys
Yo, catch my heel. You get my point?

The verse sums up her MO: She doesn’t want to be a typical late-night host, yet she’s on NBC, so ... Hey, America, give her a shot?

Three weeks and 13 episodes in, A Little Late hasn’t made too much noise just yet. Ratings have held steady, and even an offensive joke about turbans that Singh made was swiftly addressed with an earnest apology, quieting any  further backlash. Like most first-timers to late night, Singh has been experimenting with her platform, inventing new games with almost every guest and toying with high-concept digital shorts. But as it turns out, her forte so far has been the most classic of late-night responsibilities: the celebrity interview.

It’s ironic. Singh’s background as a popular YouTuber—someone used to delivering funny commentary and making viral videos for nearly 15 million subscribers—should have translated easily to the current model of late-night TV: gimmick-driven clips, lighthearted games, and deep dives. But even though her monologues cover the same topics she addressed on her channel, these brief meditations on relationships, aging, fashion, and the like come off awkward in a live-TV setting. (A set about Raya, the celebrity dating app that’s been around since 2015, felt especially stale.) Singh has made it clear that she won’t be talking politics; the goal is “to be a little more personal, a little more based in her experiences,” the show’s producer, John Irwin, told The Hollywood Reporter. But these evergreen musings feel more like rejected bits from a stand-up set than refreshing, fully formed segments that can hold an audience’s attention in the middle of the night.

As the author of the memoir/self-help guide How to Be a Bawse: A Guide to Conquering Life, Singh champions female ambition, so most of her shorts revolve around the idea of being a #girlboss. That’s a positive, largely inoffensive message, and some sketches—like the one on the wage gap set in an ’80s workout video—are clever. But the ethos of leaning in is well-trodden territory in comedy, and too many of Singh’s filmed segments rehash the idea without delivering a punch line or a fresh take.

Once Singh is sitting opposite a guest, however, she seems much more comfortable with the gig. Behind her desk, which is adorned with a picture of her dog and a stock photo of french fries—“my son and my love, together,” she explained—Singh gets a chance to cut loose and build a dynamic rapport with her guests. In these chats, Singh delivers some of her best, off-the-cuff humor. In one episode, when the comedian Chelsea Handler asked what to do with a prop during a segment, Singh responded, “You smoke it,” prompting a giggle from the usually stoic Handler.

Another night, the comedian Jim Gaffigan mentioned how clean he found Singh’s home country. “I’ve never even seen a wrapper on the street in Toronto,” he said.

“Well,” she deadpanned, “we have Drake.”

In fact, the episode with Gaffigan presented an unusual challenge for Singh. Gaffigan had been paired with Queer Eye’s Antoni Porowski, but even with two guests promoting different projects, sharing the couch and the conversation, Singh thrived, proving herself a rather adept moderator who could riff with Gaffigan on his parenting skills but also grill Porowski on how he finished his latest cookbook.

Of all the skills she developed from her YouTube days, her conversational tone made the leap to television most successfully. And even though much of the chitchat has been preplanned, as is customary with talk shows, Singh is still witty. That makes her disarming to her guests, most of whom are more used to older men in suits posing the questions in a staid atmosphere. Opposite Singh, guests are kept on their toes , but they also feel relaxed enough to settle into the couch. The actress Anna Faris even kicked off her heels as soon as she sat down.

Part of this comes from Singh’s youth. At 31, Singh is social-media savvy. She and her team have mined guests’ feeds and have clips and photos ready to display on a screen mounted between her desk and the guests’ couch. It’s a strategy that not only makes the guest seem more accessible, but also invites the viewer into the discussion. Aware of her status as the new kid on the block, Singh is self-deprecating, leaning in to her fangirl vibe rather than swapping tales of being at the same Hollywood shindig. The conversations become less formal, more breezy.

Take her sit-down with the Black-ish star Tracee Ellis Ross, for example. The two chatted about subjects Singh is well versed in—Instagram habits, their dogs. When the conversation pivoted to the challenges people of color face in the beauty industry, Singh kept the energy up. She asked follow-up questions that led Ross into telling a humorous anecdote about filming herself testing shampoos and conditioners in her shower. Videos from Ross’s phone then rolled on the screen. Clearly, the anecdote had been planned all along, but the conversation felt natural.

Every late-night host takes time to find the right footing; the genre is tough to reinvent, yet new players, especially the female ones, are expected to break the format. In Singh’s case, maybe the goal shouldn’t be to break anything at all. Strengthening one of its pillars—the celebrity interview—could be enough.