From 'Superwoman' to late night TV super flop: What ever happened to Lilly Singh?

YouTube sensation, producer, author and now late night talk show host Lilly Singh has broken several glass ceilings in entertainment, most notably as the first Indian woman to have her own late night talk show, “A Little Late with Lilly Singh."

Singh first started out on YouTube in 2010 under the alias “Superwoman,” posting rap sketches and parodies surrounding her family and Indian culture, which landed her first viral video, “Official Guide to Brown Girls.”

Back in her YouTube days, the Canadian entertainer often captured candid snapshots of daily rituals, like getting ready to go out or cleaning her room, cementing her as the "relatable Brown girl" on the internet.

Her best known videos include reactions to popular music videos with Singh in character as her Punjabi parents, sari and accent-equipped, and her content continued to gain rapport over time, launching her into YouTube glory worthy of celebrity appearances. She has since penned a book, starred in a movie and interviewed Michelle Obama.

In 2019, Singh stepped up and occupied the NBC late night time slot with her talk show, replacing “Last Call with Carson Daly.” She is credited as the first openly bisexual woman of color to do so, a token phrase that has since backfired on her noteworthy achievement. Singh has definitely made an effort to translate her YouTube dexterity into late night entertainment while maintaining her #girlboss attitude.

She opened the first episode of “A Little Late with Lilly Singh” with a rap highlighting the strides she was making for women in late night TV. Her monologues often center around topics she’s discussed on her channel, and some commentators argue that she struggles to keep it fresh. Unlike her fellow late night colleagues, Singh decided to avoid politics altogether, opting for broader subjects like dating, sexuality and race.

The celebrity interviews better accentuate Singh’s talents due to her natural ability to engage with her guests, according to Variety. The show’s initial ratings matched up to Carson Daily’s program and was renewed for a second season last May.

But, despite the preliminary praise she initially received, Singh has lately been under fire for issues that've been riding under the surface for many years.

First, the comedian has been criticized for frequently identifying as a “bisexual woman of color," so much so, that she publicly addressed it in a passive defense, and many of her sketches revolve around the fact that she isn’t a straight white man. And while being brown and bisexual are real experiences for the former YouTube star, she seems to parade those labels around like a trendy new pair of jeans.

But on a more serious note, Singh has also received backlash for predominantly adopting elements of Black and Caribbean culture (especially rap) in her videos. Her formula often entails rapping in baggy sweat suits, bold jewelry and the occasional backwards cap. 

Yes, Singh indeed grew up in Scarborough, Toronto, an area with a significant Caribbean population, but she isn’t of Caribbean or Black descent. Singh profiting off of Black culture represents a larger problem in the industry and how non-Black people of color are often given a free pass when it comes to cultural appropriation. Blackness isn’t a costume one can choose to put on at their discretion, but an identity that carries real social implications. 

Her parodies of South Asian culture also haven’t aged well either. As hilarious as they may be, some argue that they perpetuate long held stereotypes about Indian immigrants, something I myself have failed to consider. 

This speaks to American culture where immigrants are commonly made fun of for their names, accents, outfits and mannerisms. I have memories of people attempting to imitate Indian accents in school with no regard to how blatantly offensive they were being.

Although Singh has apologized in the past for making offensive jokes about her own community, she has made little effort to address the ways her caricatures affect others. According to Trinidadian-Canadian actress and activist Shivani Persad, Singh simply associating herself with Black arts isn’t the issue, but creating her brand off of it is.

We’re gradually moving on from cancel culture to an approach that allows celebrities to learn and grow, but their failure to do so can result in increasing disinterest and disappointment from audiences. 

The second season of “A Little Late with Lilly Singh” premiered in January: With a pandemic-friendly format, Singh filmed from a “fun house” and interviewed over Zoom. But, the talk show host showed no signs of amending her comedic approach or acknowledging the hurt she’s caused. Whether Singh plans to find an easy way out, she might be “a little late.”

Editor’s Note: A previous version of this article stated Singh was on “Saturday Night Live” in the headline.