Comedian Tamara Shevon mines the art of boundary-pushing to challenge norms

If laughter is a form of resistance, then Tamara Shevon – armed with a mic, her sharp wit, and an unflinching perspective on race, culture, and relationships.– is leading a full-blown rebellion. 

For over a decade now, she has sharpened her personal experiences into punchlines, delivering them with a perspective and precision that tickle the funny bone and the brain. Shevon’s comedy isn’t just about the laughs: it’s about making people look at themselves in ways they might not have before. “I like to push the boundaries to see how far you can tread the line to make people feel just a little bit uncomfortable – but also look at themselves,” she explains.

Tamara Shevon (photo courtesy of the artist)

Specifically, the Toronto-based comedian has made a name for herself through razor-sharp, hilarious social commentary, mined directly from all eras of her life, that expose the subtleties of racial dynamics. Whether she’s describing her childhood as one of the only Black kids in her suburban neighbourhood, or picking her way through the minefield of interracial dating, Shevon has a way of turning real-life discomfort into comedy through the lens of “I experienced this, and what do you think?”. 

“A lot of the experiences that I went through are just so… “ her voice trails off, before she refocuses on the bottom line: “There are so many microaggressions, so much racism packed into a lot of things that I’ve unpacked to make it more digestible for people.” The approach is comedy, not confrontation. “It’s like, ‘Oh, I guess it is weird that we do that,’ or ‘I guess I didn’t realize that you were experiencing that,’” Shevon explains. “Making it funny is a better way of approaching the situation than being like, ‘Why do you do this?’’.” She exudes a genial warmth and boasts a constant smile and easy laugh that make it easy for audiences to connect with her comedy, even when it’s challenging their perspectives.

Shevon first stepped onto the comedy stage in 2011 when she was living in China. While there, she found herself attending local comedy shows to connect with other expats. What started as a birthday dare to take the mic quickly snowballed into a calling. “There’s something about the adrenaline and the rush that you have” on stage, she recalls. “You’re like, ‘Okay, I want to do that again’! You see that you’re helping people through their days – whatever kind of day they’re having – and that was what made me want to keep going.” 14 years later, she’s still at it, with a unique and now well-honed comedic voice that continues to resonate.

A major highlight of Shevon’s year is The Underground Comedy Railroad, an annual tour featuring some of Canada’s top Black comedians. Now in its13th year (the fifth year for Shevon), the tour was founded to showcase Black voices in an industry that often tokenizes performers of colour. “The industry is weird in the sense where there’s usually just one Black person on a show because they spread them out. So it’s like being the diversity person on the showcase – which is very annoying,” sighs Shevon. By contrast, at The Underground Comedy Railroad, Black comedians “get to actually be all together, doing our art all at the same time, under the same roof in space. And it creates this electricity, especially amongst our community.”

This year’s Underground Comedy Railroad will take Shevon and fellow comedians Rodney Ramsey, Daniel Woodrow, Keesha Brownie, Simone Holder, Vance Michel, and Emmanuel Lomuro to five Canadian cities, from Montreal to Winnipeg. One of the most anticipated stops is Toronto’s Black Valentine’s show on February 14 –  where these comics will share their views on love, dating, and relationships. “Everyone on the tour has their own kind of take on what dating is like as a Black person,” reports Shevon. So the comedians will pose questions: “Are we both going through this? Is this something that you also experience? It’s gonna be nice to have a date night where everyone can experience this all together, no matter what your race is.”

Shevon’s ability to balance biting humour with inclusivity is what makes her comedy so effective for audiences of all backgrounds. A lot of non-Black “people used to be scared to go to shows that were predominantly Black shows, because they thought that they were just going to be made fun of the whole time,” she notes. “What I try to do with my comedy is come from a perspective where I’m looking at it and not judging.– but just being like, ‘Oh, I never thought that someone experienced it like that.’” Likewise, her hopes for the show are sincere and sensible: “I think this tour shows that we’re just Black people doing this because we’re not recognized in the way that we want to be,” she says. She hopes that show audiences gain “a new way of looking at comedy – like ‘Maybe I shouldn’t be thinking that there’s only-queer comedy, or only-Black comedy or only-white comedy. It’s just everyone doing comedy.”

Tamara Shevon (photo courtesy of the artist)

And for Shevon, the comedy stage is just the start. She co-hosts The Sunday Best Comedy Podcast with Saksha DC and recently released her second comedy album. And she has just recorded her first comedy special, which is set to be released later this year. The special delves into her personal journey, including her experience of navigating mental health as a Black woman – further cementing her industry status as a powerhouse performer unafraid to tackle personal and social issues alike. “When I was growing up, mental health was just not even discussed,” she says. “It was very much ‘sweep it under the rug’, ‘keep your day going’, ‘suppress everything.’” The special is an opportunity to change that narrative by using comedy to explore topics often left unspoken in Black families. “Bottom line: It’s okay to have mental issues,” she says. “It’s okay to be not okay, but still be able to stand in your truth and move forward.”

With plans for a U.S. tour and a TV pilot also in the works, Shevon’s star is on the rise. But at its heart, her mission remains unchanged: to tell her truth, make people laugh, and maybe, just maybe, change a few perspectives along the way. “No one can take that away from you,” she says. “These are my experiences as a Black woman, and I want you to be able to go on this journey with me.”

Catch Shevon on The Underground Comedy Railroad tour from until February 22, 2025, in Montreal, Halifax, Toronto, Ottawa, and Winnipeg. The Toronto stop, Black Valentine’s is on Friday, February 14, 9:00 pm at Comedy Bar Danforth (Mainroom). Get tickets at comedyrailroad.com. Connect with Shevon through her website tamarashevon.com.

© Arpita Ghosal, Sesaya Arts Magazine 2025

  • Arpita Ghosal is a Toronto-based arts writer. She founded Sesaya in 2004 and SesayArts Magazine in 2012.