Comedian, author, and actor Lilly Singh has never been one to mince words. In an exclusive conversation with Bombay Times during her Mumbai visit, the 37-year-old entertainment powerhouse delivered a powerful message about gender equality, creative respect, and the evolving landscape of digital content creation.
From YouTube Pioneer to Mainstream Trailblazer
Across an impressive 15-year career, Lilly Singh has transformed from a glittering digital sensation into a commanding voice in mainstream entertainment. While humor remains her primary forte, it's her conscientious social awareness that truly distinguishes her work. As a fierce advocate for gender equality and the first woman of colour to host a U.S. late-night show, Singh continues to disrupt industry norms and refuse conformity.
Currently in India to film a new season of her podcast Shame Less With Lilly Singh, featuring diverse Indian celebrities, the pop culture trailblazer and diehard Bollywood fan shared candid insights about her journey and perspectives.
The Digital Creator Respect Gap
Having started on YouTube when the platform was still in its infancy, Singh has witnessed the evolution of digital content creation firsthand. While acknowledging increased awareness about creators' power and reach, she highlights a significant respect deficit that persists.
"There is more awareness about the power and reach of digital creators today, but I think there's still work to be done in terms of the respect they get," Singh asserts. "A lot of times even the biggest of digital creators are viewed by brands or agencies as just numbers or stats or demographics. You won't describe actors that way."
She emphasizes the mental health implications of reducing creators to mere metrics, noting that it's neither healthy nor sends the right message about artistic value.
Hollywood's Diversity Backslide
As someone who has consistently championed diversity and representation in Hollywood, Singh offers a sobering assessment of current industry trends. Despite there being more South Asian actors in the West than ever before, she reveals that casting opportunities have actually become more limited.
"If I were to invite all the brown people in Hollywood today, I will have a full house. But if you ask any of them if it is easier for them to be cast or make movies, their answer will be no," she reveals. "In fact, in Hollywood diversity has taken a step backwards. It's even harder than before."
Singh describes a troubling pattern she observes regularly: "I go to the theatre all the time and play this game. I hang on for the previews and make note of how many films have exclusively white people. Five out of eight trailers will only have white people. You don't need all white casting for stories to be told."
Women and Comedy: Smashing Stereotypes
When confronted with the tired critique that women aren't funny enough, Singh's response is characteristically direct and unapologetic. "People who say women aren't funny are dumb," she states matter-of-factly.
She elaborates on the subjective nature of comedy, explaining, "You know what's so funny about the women aren't funny remark? It makes me laugh because comedy is subjective. I'm going to find something funny. You're not going to find it funny. It's fine. When someone goes, oh, you're not funny because I didn't find you funny. Like, baby boy, this is not for you, Ben. I'm not doing this for you. I'm doing it for this person over here."
Sisterhood at 37: Everything
Perhaps the most heartfelt revelation comes when Singh discusses the importance of female friendships in her life. "Female friendship has always been important to me but at 37, sisterhood is everything to me," she shares emotionally.
She credits women with understanding unique experiences that others cannot fully grasp, noting their ability to see pain and offer genuine empathy. "Female friendship makes me most seen," she confesses.
Singh also emphasizes the importance of women supporting each other professionally, advocating for open conversations about finances, contracts, and career achievements to foster collective progress.
Bollywood Inspiration and Mumbai Memories
As a self-professed Bollywood obsessive raised exclusively on Indian cinema in Toronto, Singh's connection to Mumbai runs deep. She recalls her first visit to the city in 2013-2014 as a core memory, particularly being invited to Shah Rukh Khan's Mannat and meeting Madhuri Dixit.
"I love the people here and the jugaad that happens. Everyone genuinely believes that tension nahi leneka, everything is workable," she says, contrasting this approach with her own tendency toward tension.
Her Bollywood upbringing continues to influence her work, sometimes creating interesting cultural collisions in Hollywood auditions. "When I do auditions in Hollywood now, they're always like, 'your facial expressions, your timing, it's all a little dramatic,'" she laughs.
Singh concludes with an open invitation to Bollywood filmmakers, calling out specifically, "I would love to do a Bollywood film! Karan, are you listening?"
Throughout the conversation, Lilly Singh emerges not just as an entertainer, but as a thoughtful advocate determined to use her platform for meaningful change while staying true to her comedic roots and cultural heritage.
