comedy Archives - Winnipeg Guardian

Tragedy Plus Time: Comedian Jeff Gobeil

June 11, 2026 Lauren Kannwischer

Winnipeg’s own Jeff Gobeil is a storyteller at heart—one who isn’t afraid to wander into the darker corners of life, as long as he brings the audience with him. Blending sharp humour with raw honesty, […]

Tragedy Plus Time: Comedian Max Macaluso

May 28, 2026 Emilea Semancik

Max Macaluso is a Winnipeg-based comedian who treats the stage like a living room and the audience like lifelong friends he just hasn’t met yet. A natural storyteller with an eye for the relatable and […]

Tragedy Plus Time: Comedian Guy Jukes

May 21, 2026 Emilea Semancik

Guy Jukes doesn’t need much runway. Built on the kind of tight, precise comedy that lands before you see it coming, his sets move fast, hit hard, and leave just enough room for the audience […]

Tragedy Plus Time: Comedian Tim Gray

May 14, 2026 Lauren Kannwischer

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 […]

Tragedy Plus Time: Comedian Cheyenna Sapp

May 7, 2026 Emilea Semancik

Cheyenna Sapp — who performs under the name Shy Sapp — is a comedian whose style she describes as raw, unfiltered, and “either very self-aware or very delusional.” Raised on the Indigenous comedy of Don […]

Tragedy Plus Time: Comedian Kristen Einarson

April 23, 2026 Emilea Semancik

Kristen Einarson is a Winnipeg-based comedian whose self-deprecating, self-aware, and observational style has earned her a growing presence on the local and national comedy scene. Shaped by a childhood spent watching Canadian staples like This Hour Has […]

Tragedy Plus Time: Comedian Dewey Parker

April 16, 2026 Emilea Semancik

Dewey Parker is a Winnipeg-based comedian who comes to the stage with one clear mission: to have fun, and to make sure everyone else does too. Equal parts silly and sharp, his autobiographical style starts […]

Tragedy Plus Time: Comedian Milan Horanski

April 9, 2026 Emilea Semancik

Milan Horanski doesn’t come to the stage with an agenda—just a genuine desire to give the room a good time. The Winnipeg-based comedian has built a following on light-hearted, conversational comedy that feels less like […]