#FIRSTLOOK: DAVE CHAPPELLE ADDED TO DEPARTURE FESTIVAL + CONFERENCE

Loft Entertainment and Oak View Group (OVG) are delighted to announce award-winning comedian Dave Chappelle will perform exclusively at Departure Festival + Conference with a stand-up show on Wednesday, May 7 at Toronto’s Queen Elizabeth Theatre at 7:00 p.m.

Registered Departure conference pass-holders will get first access to tickets with an exclusive pre-sale beginning at 10:00 a.m. on Wednesday, April 16, 2025.

A new Comedy&Culture Pass is now available, providing access to the final day of Departure conference, on May 9, featuring comedy sessions curated for insider access to the industry’s future. From navigating challenges with top executives to discovering breakout talent defining tomorrow’s comedy landscape, this pass offers exceptional value at an early bird rate of $99 until April 16.

“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 Bruce Hills, Executive Producer, Departure Comedy.

“In November we promised that comedy would be a big part in the expansion of Departure, and we are immensely proud to fulfill that commitment with the announcement of global superstar Dave Chappelle,” said Kevin Barton, Executive Producer, Loft Entertainment. “To be able to watch Dave live is one of the most coveted shows on the planet, and it’s going to be a truly magical experience for that lucky audience.”

Additional speakers and performers added to the lineup program include homegrown comedians Jasmeet Raina, Ivan Decker, Sophie Buddle, Hassan Phills, Ali Hassan, and Don’t Tell Comedy founder Kyle Kazanjian-Amory, among others. They join the previously announced How Did This Get Made? Live, Trevor Wallace, Pete Holmes, Harland Williams, Caroline Rhea, Elvira Kurt, Leslie Liao and more. Departure Festival + Conference takes place May 6-11 in Toronto.

About Dave Chappelle
Dave Chappelle is an award-winning American comedian, actor, screenwriter, and producer widely recognized as one of the most influential entertainers of his generation. He is the 2019 recipient of the Kennedy Center’s Mark Twain Prize for American Humor and the 2025 NAACP President’s Award. Chappelle’s work in television and film includes his groundbreaking sketch comedy series “Chappelle’s Show,” which became the best-selling TV show in DVD history, multiple Netflix comedy specials, and memorable guest appearances on “Saturday Night Live.”

He has earned five Emmy Awards, including three for his Netflix specials and two for hosting “Saturday Night Live” (2017, 2021), where his most recent 17-minute monologue stands as the longest in the show’s 50-year history. Chappelle has won six Grammy Awards for Best Comedy Album, including his most recent for “The Dreamer” (2025).

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CONFERENCE PROGRAMMING
Conference programming is available to Conference passholders.

Departure welcomes leading experts and notable figures in the world of comedy to speak on a range of relevant topics including the state of the comedy industry, how to build a global comedy community, and content creation and the future of entertainment. Featured speakers include:

Celebrated Comedians: Jasmeet Raina, Ivan Decker, Sophie Buddle, and Ali Hassan

Popular Creators and Influencers: Kimberly Moffit (@ask_kimberly), Tommy Schoenith (@tommy_schoenith), Max Farber (@farbsy), and Mallory Rowan (@malloryrowan)

Industry Leaders: Andrew Barnsley (CEO, Project 10 Productions & Executive Producer), Sarah Fowlie (Head of Production, Original Programming, Bell Media), Paul Telner (Head of Programming, Viral Nation), Catherine Winder (CEO/EP/Founder, Wind Sun Sky Entertainment), and Kyle Kazanjian-Amory (Founder of Don’t Tell Comedy, which has over a billion views annually)

Comedy&CulturePass is now available at an early bird rate of $99 until April 16.

For the full list of Conference Comedy Programming please visit departureto.com.

FESTIVAL PROGRAMMING
Comedy Festival programming is available to public ticket buyers with select access to passholders.

With a specific focus on exceptional homegrown talent taking place at Comedy Bar, Departure will present some of the country’s top rising comedians in two showcases:

The Departure Comedy “Breakout” Showcase, hosted by Ali Hassan, will feature eight Toronto performers making waves and on the cusp of major success:

Adam Christie

Alistair Ogden

Chris Robinson

Courtney Gilmour

Faris Hytiaa

Jackie Pirico

Sam Burns

Sam Sferrazza

The Departure Comedy “Next Gen” Showcase, hosted by Rebecca Reeds, will feature eight emerging voices from Toronto who are shaping the future of stand-up:

Ben Bayfield

Ben McKay

Bita Joudaki

Hannah Veldhoen

Harrison Weinreb

Justin Shaw

Rahul Topiwala

Sashka DC

Departure will also welcome one of the fastest-rising comedians in Canada, Hassan Phills, who will perform at Comedy Bar Danforth for an entertaining evening on May 8 and award-winning comedian Ivan Decker will host a late-night comedy surprise show at Comedy Bar Bloor featuring surprise guests on May 9.

Continuing to spotlight Canadian comedians, Departure will present New Arrivals: A Departure Solo Sketch Showcase, featuring The Second City’s top emerging performers alongside some of Toronto’s best sketch comedians, showcasing their finest solo comedy sketches. Also in partnership with The Second City, Departure will present their 90th Mainstage Revue Duel Citizens, a fast-paced comedy spectacle stacked with razor-sharp satire, hilarious songs, ridiculous characters and their signature improv comedy.

Departure will also bring Don’t Tell Comedy, the #1 global discovery platform for stand-up comedy, with two special tapings at a secret location featuring 12 of the best Canadian comedians from across the country.

FILM AND TELEVISION
An advanced screening of Harland Williams’ new comedy Wingman, produced by Justin L. Levine, a Stardust Pictures film, and also starring Kayla Wallace, Jamie Kennedy, Evan Marsh, and Russell Peters, with Williams and Kennedy in attendance for a Q&A. The screening will take place at Hotel X Toronto and be accessible to Conference Pass holders, with limited individual public tickets also on sale at departureto.com.

STACKTV is giving an exclusive first look to select Departure passholders and fans at the Season 8 world premiere of Adult Swim’s Rick and Morty before it airs on May 25. The special event, in partnership with Wax Records and Anthem Entertainment, will feature live music from Ash Molloy, ZYHIER, CON THE ARTIST, and Julian Daniel, along with games and prizes.

Departure Festival + Conference is made possible with the support of Ontario Creates.

About Loft Entertainment
Loft Entertainment invests in culture-defining talent and creative partners to tell their stories. Founded by industry veteran Randy Lennox in Summer 2023, Loft offers the world’s leading artists creative, strategic and business services across all artistic and commercial touchpoints in the music, film and media. Visit loftent.com.

About Oak View Group
Oak View Group (OVG) is the global leader in live experience venue development, management, premium hospitality services, and 360-degree solutions for a collection of world-class-owned venues and a client roster of arenas, stadiums, convention centers, music festivals, performing arts centers, and cultural institutions. Founded by Tim Leiweke and Irving Azoff in 2015, OVG is the leading developer of major new venues either open or under development across four continents. Visit OakViewGroup.com, and follow OVG on Facebook, Instagram, LinkedIn, and X.