Lilly Singh breaks the late night show glass ceiling but still has to tread carefully

“A Little Late with Lilly Singh” needs enough punch to deserve its trailblazer status without losing the warm, silly comedy that earned the host her slot.
Image: A Little Late With Lilly Singh
Lilly Singh on "A Little Late with Lilly Singh."Scott Angelheart / NBC
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By Margaret H. Willison

Late Monday night — or very early Tuesday morning, depending on your degree of reflexive pedantry — something both quite normal and circumstantially momentous occurred: An internationally beloved internet star made the leap to network television talk show host with the premiere of “A Little Late with Lilly Singh.”

By granting the 1:35 a.m. slot held for 17 years by “Last Call with Carson Daly” to Singh, a YouTube sensation with nearly 15 million subscribers, advertising partnerships with the likes of Coca-Cola and Skittles, a New York Times-bestselling advice book and her own production shingle (Unicorn Island Productions), NBC is making an incredibly savvy business decision — as is Singh. NBC gets a shot at Singh’s huge audience of young fans, and Singh gets access to the budget, staff and clear-cut celebrity of hosting a late-night TV show.

Marrying the weight of these expectations and Singh’s light-hearted comedic style resulted in an uneven but engaging debut for “A Little Late.”

But while the economics of this move might be straightforward, the actual work of breaking network television boundaries is more complicated for both Singh and NBC. On the one hand, by making this eminently practical hiring decision, NBC gets to cloak itself in a positive Glory of Firsts: It now has the only late-night network show hosted by a woman, the first hosted by an openly queer person, and the first hosted by a woman of color.

On the other hand, neither the network nor Singh, a broadly crowd-pleasing comic, are looking to reinvent the wheel. So “Late Night with Lilly Singh” has to strike a balance: Singh should deliver enough sharp, outsider observations to earn her stripes as a Revolutionary Late-Night Artist, but without drowning out the warm, silly comedy that got Singh this prominent slot in the first place.

To understand why this hiring decision is so significant, you need to remember that, prior to the announcement of Singh’s casting last spring, the best example of diversity that ABC, CBS, Fox and NBC had to offer was adding a James (Corden, of CBS’s “Late Late Show”) to the two preexisting Jimmys (Fallon, of NBC’s “Tonight Show,” and Kimmel, of ABC’s “Jimmy Kimmel Live!”). Since the inception of the late-night TV variety show in the 1950s, it has (with notable exceptions such as Joan Rivers and Arsenio Hall) been the domain of middle-aged white men in suits, the smirking comedy mask counterpart to broadcast television’s drama mask, the nightly news anchorman.

But as scandals with reporting, inappropriate workplace relationships and serial sexual harassment have come to light in recent years, bland, detached irony from besuited overlords has lost its charm, and a hunger has grown for ferociously expressed subjectivity from scrappy underdogs.

Our current raft of late-night hosts have done their best to respond to this sea change. In the summer of 2016, “Late Night with Seth Meyers” launched the segment “Jokes Seth Can’t Tell, in which show writers Amber Ruffin, who’s black, and Jenny Hagel, who’s gay, deliver the diverse-identity-reliant punchlines that host Seth Meyers can’t. It’s a good bit, but it’s also one that showcases the struggles facing late-night television: If humor is meant to take tension, anger and sadness and release them through laughter, then a lot of the jokes we need to hear the most in 2019 can’t be told by the straight, white men who are at the genre’s center.

But just because we’ve let go of the illusion that middle-aged white men in suits are neutral doesn’t mean that we’ve suddenly decided the anger of women and minorities is either commercial or mainstream, no matter how sharp the jokes it produces. And commercial and mainstream are two of the top things a talk show needs to be in order to succeed. Into this landscape steps Lilly Singh.

“A Little Late” is different not just because of its host, but also because of how it’s being created According to Singh’s Hollywood Reporter profile, the 96-episode first season is being taped in a three-month binge to be released over the course of the year so that she is free to pursue other projects in the interim. It’s an assertive move that should be applauded, but it also means that, practically, she can’t produce the kind of “hot takes” on daily political happenings that fuel so much of light-night TV (and our media at large).

In some ways, that limitation is a blessing and a relief — as Singh herself observes, audiences are just as hungry for a break from the relentless news cycle as they are for perspective on whatever fresh hell we’ve just experienced. Moreover, it is a choice that pairs well with Singh’s crowd-pleasing comedic sensibility.

But it also puts Singh in a bit of a bind. To the part of the progressive audience NBC is courting by touting this hiring choice as “trail-blazing,” Singh’s diverse identity only has so much allure if it does not generate the satirical takes on mainstream culture said identity enables her to produce. But, judging by her body of work to date, Singh is a very reluctant radical — she is a goofy, broad, friendly comedian who turned to YouTube to combat her post-graduate depression and build community, not to give vent to righteous fury. Perhaps that’s part of why Singh was was given this prominent late night slot while the aforementioned Amber Ruffin, whose jabs are more pointed, was consigned to NBC’s nascent streaming platform, Peacock.

Marrying the weight of these expectations and Singh’s light-hearted comedic style resulted in an uneven but engaging debut for “A Little Late.” While Singh has certainly done work gently satirizing whiteness, it is only because it gives her a convenient opening for her true passion: generating humor from her less-mainstream but equally funny existence as an Indian woman with immigrant parents. In the premiere, her best moments came from that impulse, such as bonding with Indian American actress Mindy Kaling over the secret thrill of being mistaken for someone as gorgeous as Priyanka Chopra (even when that mistake is fueled by white racial hegemony).

Lilly Singh, right, and guest Mindy Kaling on 'A Little Late with Lilly Singh.'Scott Angelheart / NBC

The more unsteady moments came when Singh veered towards the sharp political humor that feels more expected of her than natural to her aesthetic. She and guest Rainn Wilson opened the show with an extended bit on a white noise machine that traffics in white noises. When working in her trademark gentle satire (for instance, classifying “Birkenstocks walking across the floor of an REI to buy a Patagonia jacket" as a white noise), the jokes succeeded. But when they tried to pivot to serious commentary with Wilson claiming that a police siren signals “everything is going to be okay,” Singh failed to make a retort sharp enough for the satire to land, weakly replying, “I don’t think everyone feels that way.”

It was one of the many moments that illustrated Singh’s dilemma. She knows part of her job is to bare her teeth for our viewing satisfaction. But neither she nor NBC seem to be sure how much she should use them for truly biting humor. They want the eyeballs and breathless takes that being “A Little Late with a Bisexual Woman of Color” commands, but without forcing Singh to surrender her idenity as a unicorn-loving goofball and instead take up arms.