Dave Chappelle to Headline Toronto’s Departure Festival 2025: A Comedy Power Move

Dave Chappelle is coming to Toronto—and he’s bringing the punchlines. The iconic comedian will headline the inaugural Departure Festival + Conference with a rare, exclusive stand-up set at Queen Elizabeth Theatre on May 7, 2025.

Organized by Loft Entertainment and Oak View Group, the new comedy-focused expansion is part of a multi-day festival happening across Toronto from May 6 to 11. With support from Ontario Creates, this debut edition is already shaping up to be a cultural heavyweight.

A Massive Get for the Festival’s Comedy Launch

Six-time Grammy winner. Five-time Emmy winner. NAACP President’s Award honoree. Dave Chappelle doesn’t just perform—he commands the room. His set at Departure is being billed as one of the most exclusive tickets in town, and conference pass-holders get first dibs before the public sale.

“Having Dave Chappelle take part in Departure is a real honor,” said Bruce Hills, executive producer of Departure Comedy. Kevin Barton, executive producer at Loft, added, “Watching Dave live is one of the most coveted shows on the planet.”

Stacked Lineup of Comedians and Creators

Chappelle leads a standout lineup of comedians, from rising stars to established names:

• Jasmeet Raina
• Ivan Decker
• Sophie Buddle
• Hassan Phills
• Ali Hassan
• Kyle Kazanjian-Amory (Don’t Tell Comedy)

The schedule also includes Trevor Wallace, Pete Holmes, Harland Williams, Caroline Rhea, Elvira Kurt, and a live taping of How Did This Get Made?

Emerging talents will get their spotlight through “Breakout” and “Next Gen” showcases at Comedy Bar locations across Toronto.

Music, Film, Talks—And a Bit of Rick and Morty

Departure isn’t just about laughs. The festival includes:

• World premiere of Rick and Morty Season 8 (presented by StackTV)
• Advance screening of Wingman with Harland Williams, Jamie Kennedy, and Russell Peters
• Live performances by Bryan Adams, Jessie Reyez, Mustafa, Tegan and Sara, and Shaggy
• Visual art pop-ups from Justin Bua and Danny Hastings
• Conference talks featuring leaders from Universal Music Canada, Live Nation, and more

Award presentations will also honor Jessie Reyez with the Allan Slaight Humanitarian Award and Matty Matheson with the Cultural Innovator Award.

When & Where to Get Tickets

Dave Chappelle’s set happens May 7 at Queen Elizabeth Theatre.
Tickets open to registered conference pass-holders first, followed by a limited pre-sale starting April 16 at 10:00 a.m.

For full lineup, passes, and event info, visit departureto.com.

More…

• https://variety.com/2025/tv/news/dave-chappelle-toronto-departure-festival-1236368794
• https://www.newswire.ca/news-releases/departure-festival-conference-announces-full-lineup-and-schedule-for-inaugural-event-in-may-801633448.html
• https://www.theglobeandmail.com/investing/markets/stocks/KO-N/pressreleases/31892997/departure-festival-conference-announces-full-lineup-and-schedule-for-inaugural-event-in-may