Tim Gray is a standout in Winnipeg’s comedy scene, delivering an absurd, unpredictable style that blends pure silliness with a touch of darkness. Known for his physical comedy and offbeat perspective, he thrives on catching audiences off guard—whether through unexpected punchlines or fully committing to bits like his fan-favourite “flag” routine.
Influenced by legends like Carol Burnett and George Carlin, and modern comics such as Mark Forward and Nikki Glaser, Tim brings both classic and chaotic energy to the stage. With a meticulous pre-show ritual and a love for raw, high-energy rooms, he’s built a reputation as a comic who’s always pushing the boundaries of weird.
How would you describe your comedy style?
I tend to lean towards the absurd, the unexpected. I’ve been described as extremely silly with a hint of darkness.
Who are some of your influences?
Zach Galifinakis, Mark Forward, Jon Dore, Frankie Boyle, Carol Burnett
Who was your favourite comedian growing up?
I used to watch the Carol Burnett Show reruns on repeat. I loved the sketches and how much fun they had making people laugh. Saturday Night Live was a Saturday night fixture in our house, and even when my brother and I were fighting, we would always bond in laughter at anything Will Ferrell did. I loved old comedy albums from George Carlin, Dick Gregory, and the improvised sketches from Nichols & May.
Who is your favourite comedian now?
I love everything Mark Forward does; his latest special, Safari Time, is pure comedy gold. I’m also a huge fan of Chris Locke and love the madness of his new special. Paul Rabliauskas has more natural comedic talent in his finger than most people have in their whole body. I’m also a huge fan of Graham Clark, Brittany Lyseng, and Nikki Glaser.
What is your pre-show ritual?
I love to do write my set list out 3-4 times using less words and smaller pieces of paper every time. I do a lot of vocal warm-ups and stretch to make sure I don’t hurt myself during some of my physical jokes.
What is your favourite place you have performed? Why?
In Edmonton, there is a weekly show called Underdog Comedy that’s in a bar underneath another bar on Whyte Ave. Every time I find myself in Edmonton on a Thursday night, I love doing that show. They absolutely pack it with people, the stage is a small coffee table in the corner, the energy is amazing, and I always feel like a rockstar after a set at Underdog.
What is your favourite bit you have written and why were you proud of it?
I have a purely physical joke where I impersonate a flag. It’s my favourite to do because it catches people off guard. It’s pure silliness, and I fully commit to trying to do my best impression of a flag. It creates a fun energy in the room. It’s the only joke that I repeat that I love doing every time. Every other joke has a limited shelf life in terms of my enthusiasm for it.
I also wrote a joke for a local cable-access TV show many years ago that resulted in a cease and desist from Peter Nygard. I was pretty proud of that reaction.
What is your favourite medium for listening or finding new comics/comedians?
Podcasts are great to discover some new comedians. I still love going to open mics and seeing with the new crop of comics are talking about. Instagram usually just shoves shit into my feed, but once in a while, I’ll find a stand-up with a unique voice and a great joke.
Tell us a joke about your city.
Winnipeg is a brutal place to live. I think anyone who decides to raise kids in this city should at least be brought in for questioning by the police. It’s borderline child abuse.
Do you have anything to promote right now?
I’m part of a new podcast called “Prairie Dawgs Podcast” featuring the best comedians in Canada who pass through Winnipeg. If you like comedy, you’ll love this podcast.
Where can we follow you?
Prairie Dawgs Podcast | Instagram
PAY IT FORWARD: Who is another local comic/comedian we should know about?
