TOSketchFestBlog
Looking for the top five comedy shows in Toronto this October? Spooky season has arrived, and Toronto’s comedy scene is getting into the spirit. This month, we’ve got high-octane improv and sketch, a trip through HIStory, an all-star comedy fundraiser, and enough Halloween chaos to carry us straight through October 31st. Whether you like your comedy silly, spooky, satirical, or supporting a very good cause, we have you covered with these five shows on our October calendar.
Sex T-Rex Monthly
Monday, October 5th, 8:00pm
If you like your comedy fast, theatrical, and a little unpredictable, Sex T-Rex has given us a new reason to look forward to the first Monday of every month. Conor Bradbury, Julian Frid, Lowen Morrow, and Seann Murray are bringing their signature high-octane comedy to Comedy Bar alongside a rotating lineup of guests for 65 minutes of improv, sketch, and whatever else they decide seems cool and fun. After more than 15 years making wonderfully ambitious comedy together, we’re very happy to have Sex T-Rex on a Toronto stage every month.
Comedy Bar Bloor, Tickets + Info
LM Squared Comedy Presents “Men From Then”
Tuesday, October 13th, 7:30pm
At long last, someone is finally giving men their moment in the spotlight. Men From Then takes a dry, sarcastic trip through HIStory, introducing us to some of the notable fellas who have occupied it, from Jesus to Count Dracula. Expect dodgy wigs, curly moustaches, prolific men, and exactly the amount of reverence for the patriarchy that premise deserves. Consider our curiosity piqued.
John Candy Box Theatre at The Second City, Tickets + Info
Lusty Mannequins & Friends – Special Live Taping
Wednesday, October 21st, 8:00pm
This one has a pretty spectacular lineup and an even better reason to gather everyone together. The Lusty Mannequins (Ashley Comeau, Alastair Forbes, Connor Thompson, and Karen Parker) are joined by Guled Abdi (TallBoyz), Lil Gabi D (The Squeaky Wheel), Izad Etemadi (Orphan Black, Wine Boys), Patrice Goodman (Sunnyside, The Handmaid’s Tale), Colin Mochrie (Whose Line Is It Anyway?) and Rosie Jones (Taskmaster) for a special comedy variety show and live taping. The night is also a fundraiser close to the group’s heart (and TOsketchfest’s heart), with proceeds from the show and raffle supporting cancer care at Mount Sinai and Juravinski Hospitals, both of which have been pivotal in helping Connor kick cancer’s ass! Come for a frankly ridiculous amount of comedy talent in one room, and help raise some money for two very worthy causes while you’re there.
*Please note – this show will be filmed for a documentary television show.
**There will be an ASL interpreter at this performance.
Comedy Bar Danforth, Tickets + Info
The Dark Knightmare Before Christmas
Thursday, October 29th + Friday, October 30th
What do Batman, Jack Skellington, the Joker, a live band, and Halloween have in common? Apparently, this show. PLAYERS is mashing together Gotham and Halloween Town for a raunchy, ridiculous Halloween spectacular that’s part sketch comedy, part rock show, and part party. Brynn Bonne, Halli Hood, Mike Jankovich, Noah Hill, Pat Ronan, and Rayan Rahal are taking on the ultimate spooky crossover, and we have several questions about what happens when the Pumpkin King meets the Dark Knight. There’s only one way to get answers. AND all proceeds are donated to charity!
Comedy Bar Danforth, Tickets + Info
Humour Sketchipede’s Inaugural Super Spooky Halloween Spectacular
Saturday, October 31st, 7:30pm
Remember Humour Sketchipede from our September picks, when they were busy trying to cure death? Well, apparently that went well enough that they’ve moved on to Halloween. For their inaugural Super Spooky Halloween Spectacular, they’re assembling Summer Dad, Debit-Cash-or-Credit, Potato Potato, and Sarah Conway for a Halloween night packed with some very funny Toronto sketch and comedy talent. Costumes strongly feel like they should be encouraged, but the spectacularly long show title alone has already put us in the Halloween spirit!
John Candy Box Theatre at The Second City, Tickets + Info
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Want to see more funny in the city?
Thanks for checking out TOsketchfest’s Top 5 Comedy Shows to see in Toronto in October 2026. Like our picks? Let us know!
Have a show you would like us to know about? Contact virginia@torontosketchfest.com.
