Legendary stand-up comedian Dave Chappelle is heading to Toronto to headline the inaugural Departure Festival + Conference in Toronto for a live performance on May 7 at the Queen Elizabeth Theatre.
Tickets for Chappelle’s show will first be available to registered Departure conference pass-holders through an exclusive pre-sale beginning April 16 at 10:00 a.m.
Widely regarded as one of the most influential comedians of his generation, Chappelle has earned a reputation for pushing boundaries while skewering culture, race, and politics in his own unique way. From his groundbreaking sketch comedy series Chappelle’s Show to his award-winning Netflix specials, his work has left a huge mark on modern comedy. He is the recipient of numerous accolades, including the Kennedy Center’s Mark Twain Prize for American Humor, five Emmy Awards, and six Grammys, most recently for his 2025 special The Dreamer.
Departure evolved from the long-running Canadian Music Week, which includes a slew of concerts as well as a conference, and runs May 6-11.
The comedy component is something new to this year’s event. To coincide with the announcement, festival organisers have went ahead and launched an all-new Comedy&Culture Pass, offering access to the final day of the conference on May 9. The day will be dedicated to a deep dive into the future of comedy with curated sessions and opportunities to discover emerging comedy voices.
“Having Dave Chappelle take part in Departure is a real honour—for me, for the festival, and an amazing treat for our audiences. Starting off the inaugural Departure Comedy Festival with someone of Dave’s caliber and influence is incredibly exciting,” said Departure Comedy Executive Producer Bruce Hills.
Festival programming, open to public ticket buyers and select passholders, highlights the wealth of comedic talent across the country. Comedy Bar will host two showcase events celebrating the next wave of performers. The Departure Comedy “Breakout” Showcase, hosted by Ali Hassan, will feature eight Toronto-based comedians already making a name for themselves, including Adam Christie, Jackie Pirico, Courtney Gilmour, and Chris Robinson. The “Next Gen” Showcase, hosted by Rebecca Reeds, focuses on emerging talent such as Bita Joudaki, Ben Bayfield, and Rahul Topiwala.
Other standout events include a set by rising star Hassan Phills at Comedy Bar Danforth on May 8, and a late-night surprise show hosted by Ivan Decker at Comedy Bar Bloor on May 9.
The comedy lineup is in addition to a rather substantial music festival and conference that includes the likes of Bryan Adams and Matty Matheson at the conference and performance headliners such as Death From Above 1979, Mustafa, and the Rural Alberta Advantage.
