On Dec. 7, Brookyn comic and producer Harmon Leon is bringing two of his most popular shows to Toronto for one night of back-to-back comedy mayhem.
For one night only at the new Teddy Beer Comedy Cave (928 Bloor. St. W.) will transform into a comedy laboratory where artificial intelligence goes head-to-head with humans, and improv teams battle it out with bizarre 80s nostalgia. Whether you’re into cutting-edge tech or love the weird world of 80s pop culture, this night should provide serious laughs.
The evening kicks off with A.I. vs Human Roast Battle, a show that has taken the U.S. by storm and is now making its Toronto debut. In this futuristic comedy showdown, a human comedian faces off against an artificial intelligence in a roast battle. But this isn’t just any roast—every element, from the jokes to the avatars to the music, is created by A.I. The twist? The A.I. learns and adapts in real-time, tailoring its roasts to the comedian’s performance.
Harmon was inspired to create the show a couple of years back when he was interview a number of AI artists while working as a journalist.
“I just thought, you know, a perfect dystopian comedy evolution would be to put a human comedian in a roast battle with a machine-learning AI to decide the fate of comedy humanity,” he says.
In this edition, comedian Nicole Passmore (from Second City) will go toe-to-toe with an A.I.-generated version of Santa Claus. It’s a three-round battle of wits, insults, and machine learning, with the audience never quite sure what will happen next.
According to Harmon, each round more information is fed to the computer about Passmore and by round three she is basically in a battle against the AI version of her.
The good news is that the AI has only been victorious in two battles.
The show will feature Scott Thompson (Kids in the Hall), Miguel Rivas, and Amy Cunningham as judges.

After the roast battle, the night takes a turn to the past with That 80s Improv Challenge, a wild improv competition that celebrates the quirkiest moments of 80s pop culture. Think obscure fast-food training films, cheesy anti-drug PSAs, and the unforgettable slime dumped on young Alanis Morissette. The three improv teams competing on stage will turn these nostalgic clips into hilarious, improvised scenes, with the audience along for the ride.
Judging the competition will be Scott Thompson, Sean Cullen (The Willoughbys), and Tyra Banda (The Second City). The judges will crown the That 80s Improv Challenge Champion at the end of the night, making for a truly interactive experience.



