Why Lilly Singh Believes Representation in Entertainment Can Change the World (Exclusive) ...Saudi Arabia

Lilly Singh is used to being the first. The comedian, actress, author and entrepreneur has charted her own path in the entertainment industry, making history as the first queer woman of color and first woman of Indian descent to host a late-night show in the United States. An outspoken advocate for gender equality around the world, Singh does not take her platform lightly (she’s amassed millions of YouTube subscribers and Instagram followers), which is why she’s been named Parade’s latest Changemaker.

Raised in the suburbs of Toronto, Singh felt pressure from an early age to excel. “I grew up in a culture, which is unfortunately common in a lot of cultures around the world, where a son and a boy is considered a huge win and the daughter is considered a little bit of a burden,” she tells Parade. “I'm the second daughter in my family, and from the day I was born until adulthood, it was very clear to me that I had a lot to prove as a girl…not from my immediate family, but from extended family, from the community, from the culture at large. So that's in my DNA.”

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Singh built resilience in her youth, she explains, and found herself constantly striving for something more. “Do I think that's a fair and healthy circumstance?” she muses. “Not necessarily. Do I think that's maybe what the driving force behind my success is? Absolutely. So it's a little bittersweet.” 

Singh, now 36, was drawn to comedy as a child; it was something she learned to lean on during tough times. “With every single traumatic thing in my life, comedy has been my crutch,” she says. “Whether we're talking about like, ‘People are really disappointed you were born a girl,’ to [my] coming out, to ‘This show got canceled.’ Whatever has happened in my life…I feel like [comedy is] a way for me to test the waters, learn about myself and heal.” 

She adds, “Comedy has a way of just kind of holding you like a warm hug in very scary times.”

Courtesy of Lilly Singh

After pursuing a bachelor’s degree in psychology from Toronto’s York University (she followed in her older sister’s footsteps, she says), Singh segued into entertainment via YouTube, swiftly learning how to edit and make content online. After making her debut on the platform in 2010, Singh gained a sizable following and eventually moved to Los Angeles in 2015. There, she experienced quite the culture shock, both professionally and culturally.

“I had come to L.A. a few times, and I’ve gone to the big Cons and some creator-type events, and I always felt super out of place because it seemed like everyone else knew each other,” she reflects. “They all knew some recipe and culture that I was unaware of and I was not a part of.”

It remained hard for her to adapt, especially after leaving Toronto, a city she describes as “one of the most diverse” places in the world. She explains, “I’ve been fortunate enough to travel to many cities around the world, and [in] Toronto, you’ll see every type of person everywhere. Everyone knows every type of music, every type of food. I moved to L.A., and I was like, ‘Oh, no one I know speaks the language I grew up speaking! No one here knows what a samosa is, and no one here knows soca music.’ … It was a steep learning curve for me.” 

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Los Angeles breeds a certain “hyper-independence,” she adds, and as she continued to grow her own audience in the entertainment sphere, it became clearer just how important representation is. Thus began her work as an advocate for cultural representation through her charity, Unicorn Island Fund, which “deals with the impact of storytelling,” she explains. 

“I know from an actual research perspective that when people don't see stories featuring people that look like them, it actually can hinder the evolution of certain communities,” she says. “So much of what we see on TV and in movies is how we understand ourselves. It's how we grow. It's how conversations happen, and when those people in those TV shows and movies always look one way, that means a conversation also always sounds one way.”

Scott Angelheart/NBC/NBCU Photo Bank via Getty Images

In 2019, Singh became the first bisexual woman of color to host a late-night show, A Little Late With Lilly Singh. 

“When it was revealed to me how historic this could be and how much this could help move the needle, I was like, ‘OK, absolutely, I want to be a part of this,’” she recalls, explaining that, looking back, she had a lot of preconceived notions that were perhaps “a little naïve.”

She refers to her experience as “the myth of the table,” explaining: “I learned through that experience that getting a seat at the table doesn't matter if the table sucks, right? If the table is not going to serve you food, if the table is not going to let you be part of the conversation, if your chair is shorter at the table, if you're not getting the same meal as everyone else and the same service as everyone else, then that table actually isn't meant for you. Especially for women, especially for the BIPOC community, it is a myth.” 

Sometimes, she says, “that table is not necessarily built for us. I think the greater goal should be to build our own tables — ones where we are actually invited into the conversation and treated like equals.” 

While A Little Late With Lilly Singh ended after two years, she says she’s grateful for the experience. Since then, Singh has remained steadfast in her commitment to broadening representation, specifically through Unicorn Island, which she launched in 2021. Though it’s come with some challenges, Singh insists the hustle is “worthwhile.” Its production side is dedicated to entertainment, TV and film while the company’s charity arm has grassroots efforts mostly in India. The connecting thread? Storytelling. 

Courtesy of Lilly Singh

“Storytelling is how you change culture,” Singh explains. “It is how you change minds and what we take in, and what we watch and what we hear is really important in relation to how we treat people and how we value people.” 

She says, “I vividly remember moments in my life where I watched a movie, and suddenly I was like, I feel now like I can do something I previously did not feel I could do.”

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Singh specifically recalls her first appearance in India, where she hosted a meet-and-greet with about 200 people a few weeks after she publicly identified as bisexual. “I kid you not when I say 100 of those people came up to me simply because they saw my story online [and said], ‘This is what my experience has been.’ I think we underestimate the power of seeing people that look like you — learning, growing, experiencing things — and the power that has to unlock something in your mind to think, ‘Oh, I too can do that. I too can believe in that. I too deserve that.’”

Singh’s first feature film, Doin’ It, had a splashy premiere at the South by Southwest festival last year, and it is a perfect example of the work that she’s dedicated to making. A sex comedy à la The 40-Year-Old Virgin, Singh takes on this tried-and-true genre with her own twist. 

Courtesy of Unicorn Island

“Because it has me as the lead and has a few other characters that are also BIPOC, there’s this idea where it's considered niche, but it's not [because] it's a universal theme,” she says.

She describes the film as a “comedic commentary about a woman unlearning shame.” While that may not sound “sexy,” she insists that it is — and explains that it comes complete with her signature brand of Singh comedy. 

“If I saw that movie growing up,” she says, “I would probably feel a lot more normal in my life because I've spent a lot of years in my life [thinking], ‘Am I some sort of freak?’ I was never taught how to be sexual, and now everyone expects me to be sexual. And like, there's no manual.”

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For years, though, Hollywood has been accustomed to telling “one type of story,” she says. Through her production company, Singh aims to change all of that — to create a pathway for diverse voices to be heard and stories to be told.  

“There are certain groups of people that always are viewed through their potential. ‘Oh, they have great potential to do this, and there's so much potential for this story,’” she begins. “Then there's another group of people — women, minority voices — that constantly have to prove themselves.”

Courtesy of Lilly Singh

Circling back to A Little Late With Lilly Singh, she adds, “My late-night show [was canceled after] two seasons, and I think it's really frustrating for the narrative of any show like that or any minority show to be like, ‘Well, see, that's why it's hard to do minority stuff...’ You don't look at a spy movie with a straight white man as the lead and be like, ‘Well, that didn't work, that's why we can't do those types of movies.’

“Proof vs. potential is the ethos of my production company,” she continues. “It is like trying to rebuild the system in a way that equalizes the playing field a little bit, where groups of people don't have to keep proving themselves over and over and over again.

“At the end of the day,” she adds, “everyone deserves to see themselves in a story.”

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