While many mark milestones with a look backwards, comic Ashwyn Singh is doing the opposite: he’s writing forward. For his 30th birthday on May 2, he is staging his largest show to date Ashwyn Singh: Wrong Singh to Say at Toronto’s Winter Garden Theatre. And not with a retrospective of his greatest hits. No, this homecoming arrives with an entirely new hour of material.
“I essentially went on a 3 month BC-UK-Europe tour to write a new hour, so I can show Toronto completely new material it hasn’t seen before,” Singh explains in the middle of a sold-out run in British Columbia and before heading to the U.K., France, Germany, and Australia. The pace of creation and performance is relentless, by design: “Knowing how many people have trusted me and given me a voice, I just want to believe in myself—and work on being as honest as possible in my standup, moving forward.”
Forward motion has always defined Singh’s path. Born in India and raised in Canada after immigrating as a teenager, he initially pursued computer science at the University of Waterloo. For a time, this more conventional trajectory ran parallel to his creative life. “There wasn’t really a lightbulb moment where I thought standup was my calling,” he recalls. “I performed at open mics in Kitchener and Waterloo during my last year or two of university, and I was writing a lot about things that exasperated me, or ideas I couldn’t quite articulate.” But comedy surely and “slowly became a way to be seen and feel understood.” What followed was less a leap than firming up an existing commitment: “I just kept doing it until I knew I didn’t really want to do anything else.”
His persistence came with a cost. “I made certain personal lifestyle sacrifices, and essentially had no life for a few years,” he notes, before describing a period of negotiation with his family. “I planned for it, I told them I was going to do it, and then I did it.” The story marries humour with pragmatism: “I’m sure my parents felt anxiety about my potential success at the time. I didn’t tell them how I was living. And they didn’t tell me about their anxiety.”
While Singh’s biography may sound like a familiar story of immigrant ambition, his comedy resists easy categorization. His material — which deals with immigrant identity, religion, politics, family, and more — is sharpened by his belief that profound disagreement can be funny. “Sharp social commentary is actually the thing keeping the entire room with me in laughter,” he insists. Yes, this means that in an era shaped by algorithmic echo chambers, he is pushing in the opposite direction: “I’m not convincing people to agree with something that they don’t agree with. I’m reminding them that they can laugh at things that they disagree with—because I don’t harbor any ill intention towards them, other than to maybe call them ‘silly’ for taking everything too seriously!”
This instinct for provocation extends to his widely viewed “Desi Translations” series, in which he plays with Hindi and Urdu song lyrics for a global audience. He was initially hesitant to bring the concept onstage because “my audience is very diverse, and I didn’t want to alienate the non-Hindi/Urdu speakers in the room”. Then Singh had an epiphany: “I realized that if my objective is to truly explain those lyrics to people who don’t understand them well, and to remind my fellow Indians and lovers of Hindustani music of the lyrics that they’ve forgotten, then I must find ways to bring that to onstage performance—in a way that both groups find entertaining.” And this is what he did. Sometimes, non-speakers are fascinated by others singing along, and sometimes lovers of the music are surprised by how much non-speakers laugh at the observations he makes. The result is a shared experience that mirrors his broader comedic practice: expansive, curious, and attentive to the room.
As he approaches his 30th birthday, Singh finds himself turning some of that attentiveness inward: “I’ve officially been here for ten years, so it’s going to be a wave of mixed feelings,” he acknowledges. “I’ll feel elated that I built this. Sad that my parents won’t be here. Happy to know I’ll see them in literally a month during the India tour. Grateful for all the friends that I’ve made along the way. But mainly.. It’s good to be home.” And never fear: there will be no on-stage navel-gazing. Instead, he smiles, “I want to be as silly, angry, goofy, scared, fearless, absurd as I can be in every moment.”
His ethos is disarmingly simple, and pointedly communal. “We live in a world where it’s easier to hate what you hate than to love what you love,” he notes. “If all you see getting attention on your phone are the things you hate, let me show you that the real world is not like that.” His goal is to gather together beautiful souls: “Let me introduce you to other people who love what you love, and aren’t afraid to celebrate it.”
More specifically, he promises that “a thousand progressives of every race, gender, orientation and nationality are coming together on May 2nd to laugh at jokes made by an Indian immigrant who started doing standup comedy in Canada,” Singh says. “That’s the real milestone.”
Singh performs Ashwyn Singh: Wrong Singh to Say on May 2, 2026 at the Winter Garden Theatre in Toronto. Tickets are available at ticketmaster.ca.
© Arpita Ghosal, Sesaya Arts Magazine 2026
