Tragedy Plus Time: Toronto Comedian Hilary Henderson

Hilary Henderson is Toronto’s go-to satirical comedian, known for turning everyday situations into comedic gold. With a sharp wit and keen observational skills, Hilary brings a refreshing and hilarious take on the quirks of modern life. Her performances, a delightful blend of humour and satire, resonate with audiences as she navigates the absurdities of daily existence. A staple on Toronto’s comedy scene, Hilary Henderson is more than a comedian; she’s a laughter-inducing storyteller, transforming the ordinary into an uproarious adventure for everyone lucky enough to catch her on stage.

Hilary Henderson
Photo by: Sammie Chan

How would you describe your comedy style?

Satirical, goofy, observational, feminist, and personal.

Who are some of your influences?

For comedy: Tina Fey, Julia Louis-Dreyfus, Iliza Sheslinger, Nate Bargatze, Jon Stewart.

For life: anyone who gives me unlimited reassurance and snacks!

Who was your favourite comedian growing up?

The first person I noticed using comedy was my dad. He’s such a hilarious and goofy person. I’ve always been inspired by the way he would joke (and even make fun of himself) as a tool for connection with others.

Who is your favourite comedian now?

Taylor Tomlinson. The way she’s able to combine humour, personal storytelling, and vulnerability is amazing to watch.

What is your pre-show ritual?

Clenching so I don’t have an ill-timed nervous poop 🙂

What is your favourite place you have performed? Why?

I did a Don’t Tell Comedy show earlier this year in Los Angeles for over 200 people in a cross fit. It was so funny to me that we were surrounded by all the exercise equipment at a show. The headliner, Jessimae Peluso, hung from the gym’s rings during her set!

But my favourite regular place in Toronto is the Comedy Bar on Bloor Street.

What is your favourite bit you have written and why were you proud of it?

A comic’s role in society is to poke holes in the things that seem outrageous or contradictory. So I’m proud of any bits I’ve written that challenge something. For example, I have a bit about botox and anti-aging procedures and how men are given the luxury of being able to age (and become zaddies, yum!) and women have the expectation of looking like young hot babies forever. I’m proud of any art I can create where people walk a way feeling either more understood or having a new way of thinking about something.

What is your favourite medium for listening or finding new comics/comedians?

I can already feel people cringing from this answer, but I think TikTok is an excellent way to find entertainers and comics you relate to. In the algorithm we trust!

Tell us a joke about your city.

For free? In this economy?

Do you have anything to promote right now?

Check out my new interview series ‘F Boys at the Park’ where I sit down with guests in bizarre locations to get their hot takes on dating and heartbreak. And I’d also like to promote being kind 🙂

Where can we follow you?

Instagram | TikTok | YouTube

PAY IT FORWARD: Who is another local comic/comedian we should know about?

Ugh, it’s so hard to pick. Recently I’ve loved seeing Monica Gross and Kari Johnson. Their humour and stage presence is always on point and their work ethic is amazing.


About Emilea Semancik 106 Articles
Emilea Semancik was born in North Vancouver. Emilea has always always wanted to freelance her own pieces and currently writes for the Vancouver Guardian. She is also a recipe author working towards publishing her own series of recipe books. You can find her recipes on Instagram. @ancestral.foods