Saturday, August 29 | 8:00 PM – 10:00 PM | The Boardroom Comedy Club, 1350 St Clair Ave West, Toronto
Tickets: $15 Early Bird / $20 General Admission | 19+
Labour Day long weekend is almost here, and if you’re looking for something fun to do in Toronto before summer wraps up, Up in Jokes at The Boardroom Comedy Club on St. Clair Ave West is the move. This is a consumption-friendly stand-up show — meaning a relaxed, welcoming room where the vibe is as good as the lineup — and this month’s bill is stacked with headliners, festival regulars, and rising local talent who know how to work a room.
Here’s who’s taking the stage on August 29th, and why you don’t want to be the person who heard about it after the fact.
Ryan Hillis — Headliner
Ryan Hillis anchors this show as headliner, and it’s easy to see why. Beyond his own stand-up, Hillis is a comedian and producer in his own right — he’s behind the Cannabis Comedy Festival and hosts Laughing Buds Live on the Danforth, putting him right at the center of Toronto’s cannabis-comedy scene. He’s also released his own comedy album, Milk Day. A headliner who also produces shows brings a different kind of polish to a set — Hillis knows exactly how to close out a night on a high note.
Joe Fish — Host
Every great comedy show needs a host who can read the room, keep the energy up between sets, and get a crowd of strangers laughing together within minutes — that’s Joe Fish’s job on the 29th. A good host sets the tone for the whole night, and that’s exactly what he brings to the mic to kick things off.
James O’Hara
James O’Hara brings a self-aware, self-deprecating style built around his own life — queerness, financial hard times, and an enduring love of the band Weezer all make their way into his material with a unique, personal spin. He’s a comedy festival veteran, with credits including the Winnipeg Comedy Festival, Just For Laughs Toronto, and the Edmonton Comedy Festival, and he’s a regular finalist and runner-up on the competitive comedy circuit. He even has a debut comedy album, I Love You, And I Am Tired — which he jokes his parents rated 10/10, though he’s not totally sure they listened to it. That’s the kind of self-deprecating honesty that defines his whole act.
Nicole Rhiannon
Nicole Rhiannon rounds out the lineup with her own distinct voice and comedic point of view, adding fresh energy to a night that’s already packed with variety. If you haven’t caught her set yet, this is a great chance to see what she’s about.
Rory Moldofsky
Closing out the additions is a guest spot from Rory Moldofsky, a Toronto-based creative with a sharp eye for story and comedic timing. Guest spots are where you often catch someone on the way up — a shorter set, but no less punchy.
Why This Is the Long Weekend Show to Catch
- It’s the perfect long weekend plug-in. Toronto’s Labour Day weekend calendar fills up fast — an 8 PM Saturday show leaves you plenty of room for a late dinner after and no early alarm the next day.
- A genuinely varied lineup. From a headliner-producer to a personal-storytelling festival vet to a rising guest spot, this bill isn’t five comedians doing the same style of joke — it’s a full range of voices in one two-hour show.
- The room itself. The Boardroom on St. Clair is built around a relaxed, consumption-friendly atmosphere, so you can settle in, order something, and actually enjoy the show instead of feeling like you’re in a stiff theatre seat.
- Small room energy. Local shows like this one are where you see comedians before they’re headlining the big rooms — and where the crowd work actually includes you.
- It sells out. Early bird pricing exists for a reason. At $15 in advance versus $20 at the door, there’s no upside to waiting.
The Details
- What: Up in Jokes Toronto Comedy Show
- When: Saturday, August 29, 8:00 PM – 10:00 PM
- Where: The Boardroom Comedy Club, 1350 St Clair Ave West, Toronto, ON M6E 1C4
- Tickets: $15 Early Bird / $20 General Admission
- Age Restriction: 19+
- Note: Outside food and drinks are not permitted.
Grab your tickets before they’re gone, bring a friend (or five), and kick off your long weekend the way it’s supposed to start — laughing.
