TOSketchFestBlog
Looking for the best comedy shows in Toronto this May? If you’re looking to stay plugged into Toronto’s comedy scene, this is a good place to start. This month, we’re spotlighting one of our favourite annual improv festivals alongside four sketch shows that are building real momentum month after month. These are the rooms where new work gets tested, voices get sharper, and the community shows up. So if you want to catch what’s next (and what’s sticking around), these are the shows to put in your calendar now.
Blockbuster Week
May 11 to 16
We don’t always stray from sketch in this series, but for Blockbuster Week, we’re making an exception. Our improv cousins at Bad Dog Comedy Theatre and Sex T-Rex are bringing back this beloved festival of brand-new, fully improvised shows inspired by movies and TV. It’s fast, funny, and completely unscripted, meaning anything can happen (and usually does). If you love big swings and even bigger laughs, this is worth adding to your calendar.
Deanne Taylor Theatre, Video Cabaret, Tickets & Info
Spotlight at The Second City: Janelle McGuinness & Debit-Cash-or-Credit
Tuesday, May 12 + Wednesday, May 13
If you’re looking to keep up with Toronto’s sketch scene, Spotlight should already be on your radar. This monthly double-bill highlights two standout acts, and May’s lineup is a strong one: Janelle McGuinness and Debit-Cash-or-Credit. Two distinct comedic voices, one night, and a great excuse to see what the next wave of sketch looks like right now.
Theatre ’73 at The Second City Toronto, Tickets & Info
Monster Island
Wednesday, May 13 + Wednesday, May 27
If character comedy is your thing (and honestly, it should be), Monster Island is one of the best showcases in the city. Expect bold, bizarre, and brilliantly committed performances from some of Toronto’s funniest performers. And if you’ve ever thought “I could do that,” stick around for the free Character Bucket after the show. It’s where new bits are born!
Comedy Bar Bloor, Tickets & Info
Sketch Party: hosted by Legally Brown
Saturday, May 23
Sketch Party continues its run as one of the best way to kick off a Saturday night! Each month brings a fresh mix of troupes, solo acts, and surprises and May’s edition, hosted by Legally Brown, is shaping up to be a good one. Expect a high energy, lively vibe, big laughs, and the kind of lineup that keeps the party going all night long.
Comedy Bar Bloor, Tickets & Info
Sketch at the Rivoli
Sunday, May 31
There’s something special about seeing sketch comedy in the Rivoli Backroom, the same space where The Kids in the Hall got their start. This monthly show brings together a packed lineup of Toronto’s best and emerging sketch performers, each delivering tight, five-minute sets. A steady stream of quick-hit sketches that deliver laugh after laugh. And it’s one of the easiest ways to catch a wide range of sketch comedy in one night.
The Rivoli, Tickets & Info
Looking to turn your comedy plans into a full-on road trip?
Head to Montréal Sketchfest (April 30-May 9), or venture a little further east to St. John’s for NL Sketch Comedy Festival (May 12-17) for even more laughs across the country.
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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 May 2026. Like our picks? Let us know!
Have a show you would like us to know about? Contact virginia@torontosketchfest.com.
