Stand-up comedy in Toronto this week: 10 new dates since Oct 12, with Dave Chappelle, 5 rooms with dates in the next two weeks, tickets from CA$9.99, 2 free.
New in Toronto comedy this week
The dates: IVAN DECKER: MIDDLE CHILD (Nov 27), Nurse Georgie Carroll (Jan 24, 2027), Giggly Squad: The Gehls Gehl Tour (Feb 26, 2027), Urzila Carlson - Fatty On a Yacht (Mar 10, 2027), Jimmy O. Yang Has No Friends Tour (Apr 17, 2027), Dusty Slay: The Neighborhood Guy Tour (May 23, 2027), Gianmarco Soresi - The Misery Loves Tour (May 1, 2027), and Jeff Hobbs Headlining Live: Stand Up Comedy in Toronto | Keys Comedy Club (Oct 24), plus 2 more.
Comedy tonight and this weekend in Toronto
Tonight: Mondays Keys Toronto Stand Up Comedy Club Comedy Show Legendary Comics at Key's Stand up Comedy Club Toronto Improv Bar and Grill (20:00).
Fri Oct 23: Dave Chappelle Karmageddon at Scotiabank Arena (19:30); All Indian Comedy Show – Toronto’s Funniest Monthly Stand-up Desi Event at Key's Stand up Comedy Club Toronto Improv Bar and Grill (20:00); Friday Keys Toronto Stand Up Comedy Club Comedy Show (legends Only 2026) at Key's Stand up Comedy Club Toronto Improv Bar and Grill (20:00); Jeff Hobbs Headlining Live: Stand Up Comedy in Toronto Keys Comedy Club at Key's Stand up Comedy Club Toronto Improv Bar and Grill (20:00).
Sat Oct 24: Kyla Cobbler: Gone Rogue at The Elgin & Winter Garden Theatres (19:00); All Middle Eastern Comedy Show – Toronto’s Funniest Stand-up Event at Key's Stand up Comedy Club Toronto Improv Bar and Grill (20:00); Edgy No Filter Comedy Show (canceled Offensive Show) – Toronto Stand Up at Key's Stand up Comedy Club Toronto Improv Bar and Grill (20:00); Saturday (6 Tickets Left) At Keys Toronto Stand Up Comedy Club Show at Key's Stand up Comedy Club Toronto Improv Bar and Grill (20:00); Saturdays All Star Legends - At Keys Toronto Stand Up Comedy Club Show at Key's Stand up Comedy Club Toronto Improv Bar and Grill (20:00).
Sun Oct 25: Kyla Cobbler: Gone Rogue at The Elgin & Winter Garden Theatres (19:00); All Stars - All Black Comedy Show – Toronto’s Funniest Stand-up Event at Key's Stand up Comedy Club Toronto Improv Bar and Grill (20:00); Caribana All Black Comedy Show – Toronto’s Funniest Stand-up Event at Key's Stand up Comedy Club Toronto Improv Bar and Grill (20:00); Sunday Keys Toronto Stand Up Comedy Club Comedy Show (legends Only!!) at Key's Stand up Comedy Club Toronto Improv Bar and Grill (20:00).
Shows worth knowing
Dave Chappelle Karmageddon is at Scotiabank Arena on Fri Oct 23 at 19:30. Billed: Dave Chappelle.
Mondays Keys Toronto Stand Up Comedy Club Comedy Show Legendary Comics is at Key's Stand up Comedy Club Toronto Improv Bar and Grill on Mon Oct 19 at 20:00. Tickets from CA$30. Part of the Mondays Keys Toronto Stand Up Comedy Club Comedy Show Legendary Comics series.
Who's on
Dave Chappelle is billed in Dave Chappelle Karmageddon at Scotiabank Arena on Fri Oct 23. David Khari Webber Chappelle is an American stand-up comedian, actor, and former sketch comedian. He debuted his half-hour TV special in 1998 and his hour-long TV special in 2000. (Wikipedia) Also on our listings in Nashville (Oct 20), Charlotte (Oct 21), and Louisville (Oct 24).
The rooms
Key's Stand up Comedy Club Toronto Improv Bar and Grill (844 Bloor Street West) has 29 dates in the next 14 days and 150 upcoming in all. Listed on Comedy Atlas since Jul 2026. It regularly hosts ALL INDIAN COMEDY SHOW – TORONTO’S FUNNIEST MONTHLY STAND-UP DESI EVENT, ALL MIDDLE EASTERN COMEDY SHOW – TORONTO’S FUNNIEST STAND-UP EVENT, ALL STARS - ALL BLACK COMEDY SHOW –… Shows here: Mondays Keys Toronto Stand Up Comedy Club Comedy Show Legendary Comics, Toonie Tuesdays Keys Stand Up Comedy Club (open Mic) Toronto Comedy Show, and Stand Up Comedy (open Mic) - Workshops Free Events In Toronto Comedy Shows.
By the numbers
34 dates fall in the next 14 days. 5 listed venues have dates in that stretch. The cheapest ticket is CA$9.99, for Toonie Tuesdays Keys Stand Up Comedy Club (open Mic) Toronto Comedy Show at Key's Stand up Comedy Club Toronto Improv Bar and Grill. 2 free dates in that stretch. The busiest night is Sat Oct 24 with 5 dates. Key's Stand up Comedy Club Toronto Improv Bar and Grill has the most dates, 29. 10 of the 208 upcoming dates in Toronto were listed this week.
Full Toronto listings.