YouTube and social media sensation, Lilly Singh, with 14.7 million subscribers on the video sharing platform, has a knack for addressing serious subjects in a funny, non-preachy way. On Earth Day back in April, she posted a video in which she played the double roles of Mother Earth and a young mum, both complaining about their respective ‘children’. In under three minutes, Singh highlighted the ways in which we continue to mistreat the planet, while serving up some clever, succinct dark comedy.
Through her videos, she’s dealt with everything from unwanted male attention to the hypocritical uproar over the depiction of queer love in children’s films. Mental health is a recurring theme. Over the years, Singh has announced several breaks from social media. During the pandemic, a time when she felt like she had no purpose (as she explained to Vogue India in a recent interview), she deleted social media from her phone for seven months. “It finally allowed me to see the internet for what it is, a tool that I use, not one that uses me,” she stated to the magazine.
The book cover of Lilly Singh’s Be A Triangle
Last Monday, she announced another break. Hours after the murder of Punjabi rapper Sidhu Moosewala was reported, an introspective Singh (a fan of the artiste) came on Instagram to voice her solidarity with everyone who is feeling bogged down. “If you are feeling heavy, you are not alone… Don’t convince yourself that the internet and social media is the end all, be all. Be kind, work on your own happiness, your own mental health… so we can all collectively be stronger.”
Relearning herself
Ten years ago, the Canadian-Indian comedian was known as Superwoman, one of the world’s biggest YouTube stars. Today, Singh, 33, has added a whole series of descriptors to her name, from actor to activist, self-help author, producer, talk show host and talent hunt judge. In April, she brought out a slim self-help book, Be A Triangle: How I Went from Being Lost to Getting My Life into Shape. A book about how to be ‘your truest and happiest self’, it was promoted with Singh’s trademark quirk — photoshopped billboards on Instagram to a viral video that had Drew Barrymore doing the hook step from ‘Chura ke dil mera’. It remains to be seen if it will reach The New York Times bestseller status like her 2017 hit, How to Be a Bawse: A Guide to Conquering Life.
In the years between her two books, Los Angeles-based Singh has experienced burnout, come out as bisexual, and made history by becoming the first openly LGBTQIA+ and Indian woman to helm a late-night series on a major American television network. Then NBC cancelled A Little Late with Lilly Singh during the pandemic, after only two seasons, and it changed things. Though it had proved groundbreaking both for its host and her guests, which included Hollywood and South Asians A-listers such as A.R. Rahman, Priyanka Chopra, Vir Das and Jessica Alba, Singh says its end left her floundering.
Mindy Kaling and Lilly Singh in an episode from A Little Late with Lilly Singh | Photo Credit: NBC
“I couldn’t bounce back into anything else. So it was a hard time to let go of something that was keeping you busy and that [had been] how you’d defined yourself,” she admitted on the show, The Diary of a CEO with Steven Bartlett. One of the biggest silver linings, she says, was working on herself. Be A Triangle was a part of that.
On the day she was filming the finale of Canada’s Got Talent, we spoke to Singh about her new book, upcoming shows and staying true to your “life’s mission”. Edited excerpts from the interview:
How has implementing your own advice in the book changed your life?
More than anything else I’ve done, I’ve changed the most after writing this book. All my relationships have really flourished, whether it’s with my parents, my friends, or the people I work with. I’m way more patient because [I’ve started] really understanding people’s circumstances, perspectives and life experiences. I’ve really got into the habit of being like, ‘I don’t need to make every disagreement an argument’. [But] I’d say the biggest relationship that has improved is the one with myself. For a long time in my life, I’d been my own harshest critic, in a way that would just suck the joy out of everything. Now I’ve reached a place where I’m like, ‘At the end of the day, you have to be proud of yourself and love yourself and pat yourself on the back’.
Lilly Singh in an episode of her late night talk show, A Little Late with Lilly Singh | Photo Credit: Getty Images
What’s the difference between being a ‘bawse’ and being a ‘triangle’?
A lot of people have asked me, ‘Does this mean you don’t agree with your first book? Should we stop being a boss and be a triangle [instead]?’ I wrote these books at different points in my career and I agree with both of them. How To Be A Bawse is great for someone trying to figure out how to accomplish their goals, make a good impression, make a vision board and be the best they can be. Be A Triangle is about ‘Okay, you got all those things, you’ve accomplished your goals, but what does that actually mean?’ It encourages people to go a little deeper and get more spiritual.
Deepika Padukone recently said that Hollywood has a long way to go with representation of minorities. How much have things changed?
I think everything takes time. Is representation perfect in Hollywood? No. There’s lots of room for improvement. We’re still telling stories that are surface level because we’re still fighting against being a minority group. We still have to explain what being Indian means, what Diwali means. Having said that, I like to celebrate any progress that’s made. It’s important to recognise that there are a lot more desis on screen, whether it’s Bridgerton season two, Never Have I Ever [or] the new show I’m working on. In my ideal world, I pitch a story that’s very nuanced and complex about South Asian characters, and I don’t get notes back that are, ‘How can we make this more relatable?’ As soon as I stop getting those notes, I’ll be happy.
(L-R) Kal Penn, Versha Sharma, Lilly Singh, Simone Ashley and Maitreyi Ramakrishnan at the Bridgerton Dinner celebrating South Asian culture | Photo Credit: Getty Images
Your talk show was historic in many ways. But it also aired after 1.30 a.m. Do you feel that it got a fair chance?
That’s a complicated question because I do think everyone wanted the show to win. I mentioned this in my TED talk [this March], the system is just not set up for success when it comes to new voices. When you work with network television, your budget is decided by your time slot. So even though you’re a new voice that needs resources, when you’re the latest time slot, the newest show and the one with the lowest budget, it’s hard to get guests and to get things poppin’. That’s the system I’m trying to challenge, which is, we shouldn’t give shows budgets based on these archaic ideas [but] based on the fact that you’re trying to champion something different.
Every time Russell Peters or you perform in India, the shows sell out. What is it about Indian-Canadians that makes them so popular here?
I’ve asked myself the same question many times. And the only answer I can give you is that Canada — and I can speak to Canada and more specifically to Toronto where I’m from — is an environment that really encourages people to bring their full selves to the table. I never once felt that I needed to be anything other than who I was. I grew up being the captain of a bhangra team [and] fully immersed in Bollywood and Punjabi culture.
Lilly Singh with Russell Peters | Photo Credit: Special arrangement
It wasn’t until I moved to LA [in 2015] that I learned that people have had this experience where they weren’t encouraged to do that. A lot of times when I meet American-Indians, they know about Bollywood, but they don’t have the upbringing I had. They had to assimilate a little bit. I always felt like I could just flourish culturally. I think that’s what produces great art — when someone feels like they don’t need to change the very fabric of who they are.
Read: Why ‘The Bad Guys’ was one of the most exhilarating experiences for the makers
Who were your comedy icons growing up?
Anytime someone tells me that I remind them of Jim Carrey, I take it as the biggest compliment. The first movie I watched where people were laughing hysterically was Dumb and Dumber. I just love him, his comedic timing and physical comedy, and I’ve always tried to emulate him. Growing up in Canada being South Asian, Russell Peters was a huge, huge deal. He was my introduction to stand-up comedy, and to someone that brought [out] so much of their culture. He needs to be protected at all costs. I used to get my whole family together and watch Russell Peters specials. It was the only time [we] would really laugh at the same thing. Sure, he was making fun of different parts of our family, but none of us took offence. It was just a beautiful bonding moment for us.
You voiced your opinion about the farmers’ protests in India. But do you stay away from commenting on Indian politics?
My rule of thumb, and this has to do with global things, not just India, is I have to really believe in my heart that I am passionate about something, but also that I know what I’m talking about. That was one of the things that was tough for me in ‘late night’ because you do feel pressure to talk about everything, even though perhaps your life experience doesn’t lend you to be the best person to talk about [some of] those things.
Where to catch Lilly Singh next
Having a lot of family who are farmers, the farmers’ protests were really important to me. I recently also talked about challenging the Florida ‘Don’t Say Gay’ bill to not teach young kids about sexual orientation and gender identity. As someone who is part of the LGBTQ+ community, I feel like I can speak about that. I’ve also been really vocal about people trying to control women’s bodies.
What would you say is the biggest lesson you’ve learned in your career?
That the way to make the best art is to give yourself the permission to do so. I know that sounds really basic, but what I mean by that is, for so many years, I’ve tried to make art to be approved, to be validated, to do something for the South Asian community. And I still want to do that. But I don’t think any of that is going to ever equal success. I don’t think I will ever always please people [or] always make the South Asian community proud. I think there will always be people who don’t like what I do, don’t agree with what I do, don’t think what I do is funny. I really think that you have to remember your mission, what’s true to you, and why you started what you do. That’s been a hard lesson for me to learn. I feel like I’m in such a good place now because I’ve learned it.
The Mumbai-based journalist writes about music and pop culture.
