From YouTube to mainstream TV: Lilly Singh and Issa Rae's unconventional paths to success

In an opening musical rap number for her new show, Lilly Singh poked fun at being a different face of late-night TV.

“I know you’re used to only Jimmys in the spotlight, but I’m gonna throw some melanin up in your late night.” 

The 30-year-old YouTube star turned television host is the first bisexual woman of colour to host a late-night show on a major TV network — a point she cleverly joked about in her opening monologue during her show’s debut on Monday.

Singh, a native of Scarborough, Ont., is making headlines this week with A Little Late with Lilly Singh, which replaced Last Call With Carson Daly on NBC after 18 seasons.

Sticking true to her internet roots, A Little Late’s first-ever episode was streamed on YouTube a few hours before its cable-TV debut — a strategic decision by NBC to tap into the online fan base Singh steadily has built over the last decade through her channel, Superwoman.

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Nearly 15 million subscribers follow the YouTube account, where she uploads videos of original skits, interviews and monologues about everything from pop culture to her experience as a child of immigrant Indian parents.

Her brand of comedy resonated with an online audience and helped her land on Forbes’ list of highest paid YouTube stars in 2017. It wasn’t long before big names, including Dwayne (The Rock) Johnson and Michelle Obama, made appearances on her channel. 

A Little Late with Lilly Singh airs at 1:35 a.m. on NBC. (Evan Agostini/Invision/Associated Press)

“She essentially has been doing the job on YouTube for like the last 10 years,” said John Irwin, the executive producer of A Little Late with Lilly Singh, in an interview with CBC News.

That experience self-producing sketches and engaging interviews makes her a natural fit to host a talk show, he added.

Irwin said he first learned of Singh a few years ago, because his daughter used to watch her videos. 

“YouTube and all of these various platforms have opened the door for basically … anybody to be a star. There’s just so many ways to now find new talent,” he said. “It’s going to be interesting to watch how our business continues to morph.”

John Irwin is an executive producer with A Little Late with Lilly Singh. (CBC)

Singh’s talent and charisma sets her apart from traditional comedians who enter late-night and struggle to find their sweet spot, said Irwin, who has worked for Saturday Night Live‘s Lorne Michaels, as well as produced for Conan O’Brien and Mad TV

“There’s just that, like, uncomfortableness, where you’re watching the host trying to procure an interview, and feel natural and be funny  — and Lilly just, like, had it.” 

Singh’s first episode Monday featured comedians and stars of The Office, Rainn Wilson and Mindy Kaling. Saturday Night Live funnyman Kenan Thompson, sitcom starTracee Ellis Ross and comedian Chelsea Handler also made appearances.

Singh is pictured with NBC colleagues and fellow late-night hosts Jimmy Fallon and Seth Meyers. (Andrew Lipovsky/NBC)

While A Little Late boasts a gender-balanced and inclusive writer’s room, another distinct feature is Singh’s decision to steer away from politics — a topic that dominates late-night TV.

“[It’s] sort of a refreshing sort of stance right out of the gate, because I think you can turn on any one of these shows right now and, for the most part, you’re getting the same messaging every single day,” said Irwin.

Marty Younge, a Toronto-based arts and culture writer, has been watching Singh’s career over the years and says her versatility and existing fan base is a huge plus for NBC.

“She has tremendous crossover potential, because she’s already demonstrated, as a Youtuber, the ability to make a lot of content … content that resonates with a large fan base and a younger fan base that is advantageous to them.” 

Marty Younge is a Toronto-based arts and culture writer. (Sharon Wu/CBC)

Younge also points to the changing nature of late-night TV, with hosts creating catchy, viral videos that live beyond the early-morning audience and rack up millions of views online. It’s likely another reason NBC plans to make sure A Little Late has a strong online presence.

“Who better to make that digital content other than Lilly Singh?” she said.

Still, Singh, who is used to working with a small team, will have to adapt to performing in front of a studio audience and working with a large team of writers. “It will be interesting to see how she transitions into the new medium without alienating her old fans,” said Younge.

One of the first examples of someone who has successfully made the transition from YouTube to mainstream television is Emmy-nominated actress Issa Rae.

Rae is the star, executive producer and writer of HBO’s Insecure, now headed into its fourth season. But Rae got her start on YouTube, where she launched her comedy web-series Awkward Black Girl in 2011.

Issa Rae first drew attention with her YouTube series Awkward Black Girl. She’s also the creator, co-writer and star of HBO’s Insecure. (AFP/Getty Images)

The show soon caught the attention of comedian and producer Larry Wilmore, who gave Rae her first break and helped her write and create her first TV pilot.

“I’m here because the internet,” Rae said in an interview with CBC News, talking about her unconventional path. “There wasn’t a blueprint for getting your show on television.”

Watch Issa Rae talk about paving a new path in Hollywood:

The actress, creator of Insecure and executive producer of Black Lady Sketch show talks about making her own way, representation and how the Internet is giving creative people more opportunities than ever. 2:54

Since the success of Insecure, Rae has starred in a number of film projects, including Little and The Hate U Give. She’s also the executive producer behind HBO’s A Black Lady Sketch Show, a sketch-comedy late-night series that features a black female director, cast, and writer’s room. It was recently renewed for a second season.

Rae says it’s inspiring to see how talent born out of the digital space can break barriers in film and television today.

“I see a lot of leaders, I see a lot of people opening doors,” she said. “I see us taking the reins on a lot of our content.”

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