20 Years of Laughs: Comedy Monday Night’s Enduring Legacy in Calgary

For nearly two decades, Comedy Monday Night has been the beating heart of Calgary’s comedy scene. As it approaches its 20-year milestone, what began as a simple open mic night has grown into Canada’s longest-running comedy open mic and a vital cornerstone of Canadian comedy.

20 Years of Laughs: Comedy Monday Night's Enduring Legacy in Calgary
James Moore on stage. Photo provided by Comedy Monday Night.

From Humble Beginnings to Comedy Institution

When James Moore launched Comedy Monday Night in March 2005, Calgary’s comedy landscape was barren. Moore, who didn’t step on a comedy stage until he was 43, recognized a critical need—comedians required stage time to develop their craft, and Calgary offered precious few opportunities. Starting in the basement of Dickens Pub with little more than determination and a sign, Moore created what was initially a struggling weekly event playing to mostly empty rooms.

Fast forward to today, and Comedy Monday Night has become a comedy powerhouse that has outlasted numerous venues (from Dickens to Lord Nelson’s to Broken City, and now Modern Love YYC) while maintaining its core mission: giving comedians a place to find their voice.

The Comedy Classroom

What makes Comedy Monday Night special isn’t just its longevity but its role as what comedian Trent McClellan called “school.” For many aspiring comics, the show functions as a comedy classroom, gym, and sometimes dungeon—a place where talent is forged through practice, feedback, and, occasionally, failure.

20 Years of Laughs: Comedy Monday Night's Enduring Legacy in Calgary
Trent McClellan on stage. Photo provided by Comedy Monday Night.

Moore’s approach has always been part mentor, part drill sergeant. First-timers receive a notebook and pen (a CMN tradition), along with blunt advice: “Having fun is the best you can do. But you only have five minutes. Do not go over your time. Otherwise, I won’t book you again for a while.”

This structure and discipline have become Comedy Monday Night’s hallmark. Comics who develop here are known throughout Canada for their professionalism—arriving early, respecting time limits, mastering microphone technique, and taking hosting duties seriously.

Nurturing Canadian Comedy Talent

The Comedy Monday Night alumni list reads like a who’s who of Canadian comedy success stories. Karen O’Keefe performed on the CMN stage for the first time and went on to national TV appearances and major festivals. Trent McClellan developed material that propelled him to become a cast member on CBC’s “This Hour Has 22 Minutes.” Allyson Smith built an act that took her from Calgary to international success.

20 Years of Laughs: Comedy Monday Night's Enduring Legacy in Calgary
Karen O’Keefe on stage. Photo provided by Comedy Monday Night.

The Raw, Unfiltered Experience

My recent visit to Comedy Monday Night at Modern Love YYC captured what makes this show special. The venue itself embodies the spirit of the event—a little rough around the edges but warmly inviting, serving up comfort food alongside raw, unfiltered comedy.

Not every joke landed, and others pushed boundaries with adult or politically incorrect content. But that’s the beauty of Comedy Monday Night. It’s raw, authentic entertainment where comics try new material. The audience knows what they’re in for and enjoys being part of the process.

What struck me most was the feeling of community. Despite the clear camaraderie among regular performers and staff, newcomers (both on stage and in the audience) are welcomed without pretension. There’s an authenticity to the experience that feels increasingly rare in our curated entertainment landscape.

20 Years of Laughs: Comedy Monday Night's Enduring Legacy in Calgary
Allyson Smith on stage. Photo provided by Comedy Monday Night.

Beyond the Spotlight

Perhaps most remarkable is Moore’s approach to the business side. Despite consistently attracting paying audiences for nearly two decades, he has never taken a cent from Comedy Monday Night shows. Revenue goes toward paying performers, advertising, merchandise, and supporting charities like the Calgary Drop-In Centre and the Epilepsy Association of Calgary.

This generosity of spirit extends to the broader comedy community. Rather than viewing other open mics as competition, Moore frequents them and supports their organizers. This collaborative approach has fostered a uniquely supportive comedy scene in Calgary.

A Canadian Cultural Treasure

Comedy Monday Night stands as a true Canadian cultural treasure after nearly 20 years. In a country that often waits for its artists to find success elsewhere before claiming them, CMN represents homegrown talent development at its finest.

In Moore’s own words: “I believe that I’m making a contribution and a difference… Because one day, one of these kids who took their first step ever onto our comedy stage is going to make it big. And when they do, I’ll be right there to open for them.”

You can catch Comedy Monday Night every Monday at 7:30 pm at Modern Love YYC. Tickets are available at the venue or online. Here’s to 20 more years of laughs.

 

About Josie Simon 20 Articles
Josie Simon (she/her) is a writer, passionate LGBTQ+ advocate, and lover of the arts. As a former dancer with a keen eye for detail, Josie brings a unique perspective to her writing. She is a current fourth-year political science major at the University of Calgary and has previously contributed to the Gauntlet.