Schedule. Everything happening at Departure

Be the first to witness the next generation of Canadian comedy talent! This showcase features eight emerging comedians from Toronto who are quickly making a name for themselves. With fresh perspectives and bold new material, these rising voices are shaping the future of stand-up.

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).

The stage is set for Canada’s hottest rising comedians! Featuring eight of the country’s top breakout acts from the Toronto area, this industry showcase highlights performers making waves and on the cusp of major success. Expect razor-sharp wit, standout performances, and an unforgettable night of comedy.

A must-see showcase featuring eight of Canada’s top breakout comedians from the Toronto area who are making waves in the industry. Get ready for sharp, original, and unforgettable performances from rising stars.

Elvira Kurt is a Canadian Screen Award, Canadian Comedy Award, Cannes Film Festival Award-winning, trail-blazing, blazer-wearing, queer. comedy. icon. A regularly recurring guest co-host on CTV’s The Social, she’s done a ton of cool sh*t including: I Have Nothing (Crave), POTUS (Segal Centre For Performing Arts, Montreal) The Great Canadian Pottery Throwdown (CBC) Drink Masters (Netflix), Canada’s Drag Race (Crave), The Great Canadian Baking Show (CBC), Cross Country Cake Off (CTV), The Fabulous Show (Family Jr.), popcultured with Elvira Kurt (The Comedy Network), Spin Off (Game Show Network), Baroness Von Sketch Show (Prime) , DeGrassi: The Next Generation (CTV/ Netflix), Miss Persona (Treehouse), Still Standing, This Hour..., The Debaters and, ‘q’ (CBC). Then there’s solo theater shows, tours, comedy special tapings, festival appearances and two projects in development -a film AND a sitcom- all of which make Elvira one busy teacup butch! Hosted by Canadian Comedy Award winner Robert Watson.

Experience eight of Canada’s most exciting sketch comedy performers from the Toronto area as they bring their sharp writing and dynamic characters to the stage. A night of fast-paced, high-energy comedy you won’t want to miss!

Departure presents New Arrivals: A Departure Solo Sketch Showcase. Created in partnership with The Second City, which has played an important role in developing new sketch comedy talent, this show will feature The Second City's top emerging performers alongside some of Toronto’s best sketch comedians, showcasing their finest solo comedy sketches. Expect a night of fresh, bold voices shaping the future of comedy.

Comedian and Actor Harland Williams is known the world over for his hilarious movie roles and outlandish stand up and sketch comedy routines. From his unforgettable roles in films such as Dumb and Dumber, Something about Mary, Half Baked, Rocketman, Sorority Boys, Down Periscope and so many more. Harland has been described as a scene stealing actor whose unique portrayals of his characters keep them etched in the minds of filmgoers everywhere. Add to this his incredible stand up comedy routines, which have been seen on Letterman, The Tonight Show, Conan O’Brian, HBO, Comedy Central and everywhere else. Described as sharp, witty, unpredictable and original; Harland is the true master of joke telling and crowd interaction. His improvisational skills led to him winning the award for best improviser on NBC’s prime time series, ‘Thank God You Are Here’ (available on YouTube). Harland Williams is the rare comic artist who has managed to master both Stand Up and Sketch comedy and combine them both masterfully into his shows. Fresh, funny and always full of the unexpected, Harland’s incredible shows are not to be missed.

Trevor Wallace is a stand-up comedian, writer & actor. Wallace can be seen just about everywhere on the internet and has collectively built a digital thumbprint of over 2.5 Billion views across his social media channels with a following of over 16 Million fans collectively. Wallace has been featured on Comedy Central, MTV, Barstool Sports, E! News, The L.A. Times, The New York Times, Ad Age, Business Insider, Men’s Health, Buzzfeed, and Complex to name a few. Wallace was also voted as a finalist for “Best in Comedy” at the 2020 Shorty Awards. Wallace has worked with prestigious brands such as, Chipotle, Natural Light, BruMate, SeatGeek, G FUEL, OnePlus, Bumble, Wetzel’s Pretzels, Snickers, Monster Energy & many more. Wallace has also toured the U.S. performing at theaters, colleges and comedy clubs including the Netflix Is A Joke Festival, Moontower Comedy Festival and the New York Comedy Festival. This past year Trevor wrapped up his SOLD OUT Theater tour ‘Are you That Guy’ which was an international success. His first hour long special Pterodactyl, is now streaming on Prime Video.

The fastest-rising comedian in Canada, Hassan Phills is putting on a show you won’t forget! If you're in the audience, prepare for a night of exceptional storytelling and quick-witted crowd work, creating a close and personal experience you won’t want to miss. Recently featured in Crave's original series The Office Movers, Hassan has solidified his place in Canadian entertainment as a dynamic and influential figure.

Leslie Liao is a stand-up comedian, actress, and writer. Audiences around the world have been drawn to her relatable, introspective, and matter-of-fact style of humor which is often anchored around her experiences as a single Chinese-American woman living in Los Angeles. Leslie was recently selected to be a New Face of Comedy at Montreal's prestigious Just For Laughs Comedy Festival 2023, and her debut set on Don't Tell Comedy platforms, “Fixing Straight Men,” debuted boldly on YouTube with clips from her set going viral on Instagram and TikTok. She will next be seen in the new multi-comic standup series on Netflix called “Verified Standup” which will debut on the platform later in 2023. Leslie has toured with some of the biggest names in comedy, including Fortune Feimster, and can often be seen in Los Angeles gracing the stages of The Comedy Store, Hollywood Improv, Laugh Factory, Flappers, and many more.

Get ready to dive into the depths of cinematic absurdity with the podcast that celebrates the best of the worst: How Did This Get Made. Join the dynamic trio of Paul Scheer, Jason Mantzoukas, and June Diane Raphael as they expertly dissect and hilariously roast some of the most mind-boggling movies ever Made. With a combined resume that includes hit shows like The League, Black Monday, Brooklyn 99, Grace & Frankie, and Long Shot, these hosts bring their comedic genius to every episode of How Did This Get Made. Together with their funniest friends, they subject themselves to a cinematic nightmare, leaving no ridiculous plot twist or cringe-worthy dialogue unturned. It's no wonder that How Did This Get Made is consistently ranked among the top 10 most downloaded comedy podcasts. This multi-award-winning show took home the prestigious 2022 Ambie Winner for Best Comedy Podcast and was crowned iHeart Radio's Best TV & Film Podcast. But How Did This Get Made doesn't stop at audio entertainment. Brace yourself for an unparalleled live experience that has captivated sold-out audiences across the country. During the live episodes, you become part of the action, engaging with the hosts through questions, spontaneously creating uproarious songs for segments, and witnessing unforgettable clips that can only be described as one-of- A-kind. From the hilariously absurd Drop Dead Fred to the adrenaline-fueled chaos of the entire Fast and Furious franchise, How Did This Get Made fearlessly deconstructs and mercilessly mocks the most epically bad films ever created. It's a rollercoaster ride of laughter, astonishment, and shared disbelief that you won't find anywhere else. Join the How Did This Get Made community and immerse yourself in the realm of cinematic train wrecks. It's a podcast that defies expectations and guarantees a one-of-a-kind experience. Get ready to have your mind blown and your funny bone tickled like never before.

Award-winning comedian Ivan Decker is a comedy powerhouse, recognized as one of the best in the country. His sharp wit and impeccable timing have graced major media outlets like CBC, CTV, TBS, and more. You've seen him on hit shows such as The Debaters, Just for Laughs, and CONAN, not to mention his half-hour special on NETFLIX. In 2017, Ivan was named a "Comic to Watch" at the New York Comedy Festival. In 2018, he made history as the first Canadian in 34 years to win a JUNO award for Comedy Album of the Year. Hailing from Vancouver, he has captivated audiences nationwide and internationally with a diverse array of performances. From headlining comedy festivals across North America and Europe to joining prestigious tours like the Just for Laughs Road Show, Ivan has also featured prominently in high- profile comedy series like Rick Mercer's Comedy Night in Canada and Comedy Central's Stand-Up Showcase. Chortle Magazine in the UK hails his clean, sharp comedy as "smart, original, and slickquot; His sophomore comedy special "Popcorn" released on YouTube in early 2024, has garnered widespread acclaim, and resulted in Ivan’s second JUNO nomination, further cementing his status as a comedic tour de force.

Pete Holmes is the creator and star of HBO's Crashing (produced by Judd Apatow) and TBS' The Pete Holmes Show (produced by Conan O'Brien). He's also the star of CBS' How We Roll as well as two HBO stand-up comedy specials. Pete's also the voice of the e*trade baby and was a guest writer/star on multiple episodes of The Simpsons. He's also proud to be the dumbest Batman on YouTube (Badman), the host of the wildly popular You Made It Weird podcast and the author of Comedy Sex God. He wrote this bio in third person. He napped shortly thereafter.

Caroline Rhea is a stand-up comedian and actress, best known for her role as ""Hilda Spellman” from the hit series ‘Sabrina The Teenage Witch’ and her numerous comedy specials. She voices “Linda Flynn Fletcher”, the mom, on Disney’s hit series, ‘Phineas and Ferb’. Caroline has starred in many films including Unbearable with Julia Stiles, and last Christmas, Hallmark’s Holiday Mismatch and A Mrs. Miracle Christmas as “Mrs. Miracle”. She has appeared in many comedy series including NBC’s Lopez vs. Lopez and Jon Cryer’s Extended Family. Caroline hosted her own talk show and has been a regular panelist on several game shows including Funny You Should Ask, Match Game, Name that Tune, and Hollywood Squares. She recently filmed her 7th comedy special at the Sydney Opera House. Caroline tours comedy clubs throughout the world and still makes time for hosting and serving as an auctioneer for corporate events and numerous charities.

Don’t Tell Comedy is bringing their premier stand-up comedy showcase to Toronto as a part of the Departure festival to highlight and amplify some of the best comedians from all over Canada. Over the last three years Don’t Tell has cemented itself as the number one discovery platform for stand up comedy globally and has helped launch the careers of comedians like Ralph Barbosa, Malik Elassal, Michael Longfellow, Susan Rice, and more! Don’t Tell Comedy’s stand up clips garner over 1.2 billion views annually, with over 8 million followers on its social media channels. The live tapings are scheduled for May 10 at a secret and very unique location in Toronto that will be released the day of the show to ticket holders.

Jamie Kennedy is a comedian, actor, and writer known for his breakout role as Randy Meeks in Scream and Scream 2. He first gained attention in Romeo + Juliet alongside Leonardo DiCaprio before becoming a household name with The Jamie Kennedy Experiment (JKX), which became The WB’s highest-rated show. His fan-favorite character, Brad Gluckman, a wannabe rapper from Malibu, later hit the big screen in the cult comedy Malibu’s Most Wanted. Jamie has appeared in films like Kickin’ It Old Skool, Son of the Mask, Tremors, Three Kings, Enemy of the State, Harold and Kumar, and Boiler Room. He’s also lent his voice to The Cleveland Show and Legends of Chamberlain Heights. With multiple comedy specials and over 190 episodes of television under his belt, Jamie continues to tour nationwide, bringing his sharp wit and unique perspective to audiences everywhere. You can also find him hosting his podcast, Hate To Break It To Ya, where he dives into Hollywood, culture, and everything in between.

Proudly celebrating 52 years in Toronto, The Second City presents their 90th Mainstage revue! Duel Citizens is a fast-paced comedy spectacle stacked with razor-sharp satire, hilarious songs, ridiculous characters and, of course, the signature improv comedy that The Second City is world famous for. Written and performed by a completely Canadian cast and crew, this show joyfully skewers politics, pop culture, and everything in between. From full-blown national tantrums to the absurdities of daily life, come laugh with The Second City as we turn chaos into comedy.