#FIRSTLOOK: “HOW DID THIS GET MADE” LIVE AT DEPARTURE FESTIVAL + CONFERENCE 2025

By Justin Waldman

Last night, I had the distinct pleasure of attending the How Did This Get Made? live Podcast recording at Massey Hall, as part of Departure Festival + Conference 2025. The Podcast celebrates bad films and on this episode, they took a look at the absolutely indescribable farce that is Sylvester Stallone’s 1991 film, Oscar. This one of the most bizarre, hellish, insane things I’ve ever seen. The exact opposite of what I’d describe a HDTGM live show though, actually. And for someone who attended their first HDTGM show, I would absolutely return time and again at another opportunity, no matter how unlikely as though one audience member had to call out to June Diane Raphael “Why do you hate Toronto?”.

While Paul Scheer told us a story (we swore not to repeat the story and he made a note to get it edited out of the taping!) about 2017 film Governor Gabbi, the Podcast recording itself was insightful and engaging. They talked for about 45 minutes about the sheer madness of disastrous film Oscar, and a movie Stallone (according to an audience member who researched it) said is the second worst thing he’s done in his career behind 1992’S Stop! Or My Mom Will Shoot.

Rounding-out this Podcast trio is Jason Mantzoukas who is as unhinged as he is on all things he’s done and is most likely recognized from. This Fan Q&A and taping truly was a night that never to be forgotten!

Without wanting to ruin the Podcast episode before it airs, we won’t divulge into other information that Paul, June and Jason reveal during the taping. If you have never listened to How Did This Get Made? before, you easily will become a fan. This was truly magical witnessing this live!

#FIRSTLOOK: DEPARTURE FESTIVAL + CONFERENCE 2025 HIGHLIGHTS – MATTY MATHESON, TEGAN AND SARA, DALLAS GREEN, GRACE VANDERWAAL, “HOW DID THIS GET MADE?” AND MORE

The Departure Festival + Conference has officially taken flight in Toronto, running now through May 11, 2025. Having grown alongside Canadian Music Week, this reimagining of that 44-year Festival focuses on not only Music, by Comedy, Entertainment and Technology forming a hub for the likeminded. Based primarily out of Hotel X and venues surrounding the area, this inaugural edition of the Festival is lifted by some major starpower.

The Departure Honours Gala served to celebrate and honour Canadian creatives and Artists who have made significant impact through their work and coming to receive their flowers this year included chef and actor Matty Matheson, Dallas Green (also known as City and Color), along with presenters and performers Tegan and Sara, Jessie Reyez, Jully Black and so much more. Above this, names like Dave Chappelle, Grace VanderWaal, Paul Scheer, Jason Mantzoukas, June Diane Raphael, and more have shows around town.

Some highlights from the Red Carpet, evening hosted by eTalk‘s Tyrone Edwards and Traci Melchor:

 

 

 

 

 

View this post on Instagram

 

 

 

 

 

 

 

 

 

 

 

A post shared by William Wong (@mrwillwong)

Day One of the Festival kicked things off on a high note. Our Justin Waldman and Genevieve Walker sat-in on some fascinating talks with Music icons Bryan Adams and Shaggy as they reflected upon their careers and where they are today. Adams mentioned he’s recording a radio show for IHeart Radio which will be airing soon, setting-up a studio in his hotel suite while he was here. Shaggy who knows Toronto very well, talks about evolution of that Jamaican swag, and being an honourary Canadian having won a JUNO Award for his album HOT SHOT.

 

 

 

 

 

View this post on Instagram

 

 

 

 

 

 

 

 

 

 

 

A post shared by William Wong (@mrwillwong)

Day Two was highlighted not only by the first ever DEPARTURE HONOURS Gala, but guests of the Festival got to attend in-conversations with Matty Matheson (treated to free Matty’s Patty‘s burgers, nonetheless), Dallas Green, and also duo Tegan and Sara focused their conversation on their Tegan and Sara Foundation. Later in the evening we were so lucky to catch Grace VanderWaal on her Childstar Tour at Great Hall where she delivered a spellbinding hour-long set, both stylized and polished.

 

 

 

 

 

View this post on Instagram

 

 

 

 

 

 

 

 

 

 

 

A post shared by William Wong (@mrwillwong)

Justin Waldman will be checking-out HOW DID THIS GET MADE? Podcast at Massey Hall tomorrow night and we’ll be sure to deliver the highlights from this eagerly-awaited show! Be sure to check back!

(Photo/video credit: Justin Waldman/Genevieve Walker/Mr. Will Wong)

#FIRSTLOOK: DEPARTURE FESTIVAL + CONFERENCE 2025 PREVIEW

By Justin Waldman

The Departure Festival + Conference is kicking off its first year this year and it is starting with a bang! Formerly known as Canadian Music Week, Departure Festival is combining Music, Comedy, Tech, and the Arts, to bring forth an incredible first year with talks, performances, and must see events and awards. We are going to highlight five events we cannot wait for. In no particular order here are our top events to look forward to at the Departure Festival to look forward to.

DAVE CHAPPELLE
Does this man need any introduction. Despite his outspoken comments that certainly make him a polarizing figure, there is no denying how influential and massive of a name Dave Chapelle is, he is arguably on the “Mount Rushmore” for most people when it comes to Comedy, so having him be part of the inaugural Departure Festival is a huge feet.

MATTY MATHESON
If you don’t know the name Matty Matheson, where have you been? He is a multifaceted Entrepreneur who does everything from launch restaurants or be partners in them (Bar Clams, Prime Seafood Palace, Maker Pizza, Ca Phe Rang, Rizzo’s House of Parm) and is going to be sitting back and talking at the conference, he is also an Actor whose been part of principal Cast in F/X‘s The Bear.

BRYAN ADAMS/DALLAS GREEN/MAX KERMAN/SHAGGY CONVERSATIONS
I don’t think any of these men need an introduction at all, Green who is the co-lead singer of Alexisonfire and the lead of City and Colour, as well as Max Kerman whose on a book tour of his newest book and the frontman of The Arkells, and then Shaggy and legendary Canadian Bryan Adams do not need an introduction, they’re iconic in their own right and have multiple acclaims and having the privilege to hear them talk about their careers would be a highlight.

HOW DID THIS GET MADE?
If you’ve never heard of this podcast then you’ve been missing out, it’s a dynamic trio of Paul Scheer, Jason Mantzoukas and June Diane Raphael and they discuss how some of the most baffling and questionable movies ever got made. It’s a hilarious insightful podcast that simply cannot be missed.

DEATH FROM ABOVE 1979/QUAVO SHOWS
Two of the premium music events happening as part of Departure Festival this year, with Death From Above 1979 playing two incredibly intimate shows at Lee’s Palace and Quavo playing History. These two shows are must see and a great inclusion and the incredible line up of talent that is part of Departure Festival.

The 2025 Departure Festival + Conference runs from May 6th to May 11th and all information can be found here: https://www.departureto.com, so get ready to take flight!

#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).

---

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.

#NEWMUSIC: TIA WOOD, DALLAS GREEN, AND TEGAN AND SARA TO APPEAR AT DEPARTURE HONOURS 2025

In advance of Canadian music’s biggest weekend, Loft Entertainment and Oak View Group (OVG) announced Departure Honours, an intimate reception showcasing and celebrating notable changemakers, emerging voices, and milestones within the music industry. Dallas Green (City and Colour), and Tia Wood to perform at the event, alongside a special presentation by Tegan and Sara, highlighting their foundation’s mission to invest in the potential of 2SLGBTQ+ communities.

Bringing the community together to honour the past and celebrate the future, Departure Honours includes the Lifetime Achievement Award presented to Neill Dixon, former President & CEO of Canadian Music Week (CMW) for his longstanding contribution to the industry; the Independent Achievement Award presented to Dallas Green which recognizes his groundbreaking success as an independent artist, marking the 20th anniversary of his debut album Sometimes (released on Dine Alone Records); and an Industry Achievement Award presented to SOCAN in celebration of the organization’s 100th anniversary. Other honours to be handed out on May 7 include the Trailblazer Award, that goes to a woman in broadcasting who has had a great impact on the industry. More honourees and awards to be announced in the coming weeks. Departure Honours takes place on Wednesday, May 7 at Hotel X Toronto, in its New Fort Hall kicking off at 6:00 p.m. ET.

“In building Departure, we wanted to ensure there was a moment for us to come together to toast some of our industry’s most impactful artists and changemakers,” said Kevin Barton, Executive Producer, Loft Entertainment. “These individuals are instrumental in helping to create the vibrancy of Canada’s arts and music culture and we are proud to host them at our event in May.”

Additionally, Loft Entertainment and Oak View Group (OVG) announce key partners and sponsors for Departure Festival + Conference’s inaugural event. Major players included are Amazon Music, Anthem Entertainment, Beatdapp, Canadian Independent Music Association (CIMA), Exclaim!, Hotel X Toronto, Live Nation Canada, Music Canada, Paquin, Pattison Outdoor, Plugz, Seeing Red, Slaight Music, SOCAN, Sony Music Canada, Ticketmaster, Toronto Star, and Warner Music Canada. The support of these industry leaders is integral to this year’s Festival and Conference, and provides the framework for Departure to connect artists, fans, and innovators across music, art, comedy, and tech. Taking place from May 6-11, Departure will span 40+ venues across Toronto and showcase 100+ emerging and established artists.

“We are very fortunate to have the support of some of the most respected organizations in the music, entertainment, hospitality and business sectors,” said Tom Pistore, President of Oak View Group Canada. “This level of collaboration and partnership is a true testament to what we are building with Departure and the footprint it will have in the calendar in the years to come.”

Departure also acknowledges support from Ontario Creates, and Canadian broadcasters including Bell Media, Central Ontario Broadcasting, CHIN Radio, Corus, Durham Broadcasting, Evanov Communications, iHeartRadio, Pattison Media, Rogers, SiriusXM Canada, Stingray, and Whiteoaks Communications Group.

Departure Honours ticket pre-sale begins today at 12:00 PM EST at departureto.com with general on-sale beginning on April 8, 2025.

#FIRSTLOOK: FEFE DOBSON, MAX KERMAN, TEGAN AND SARA AND MORE ADDED TO DEPARTURE FESTIVAL + CONFERENCE LINEUP

Loft Entertainment and Oak View Group (OVG) today announced world-renowned artists and speakers joining this year’s Departure Festival + Conference. Decorated music artists Tegan and Sara, Max Kerman, Fefe Dobson as well as comedy icons Elvira Kurt and Jamie Kennedy join previously announced guests including Bryan Adams, Dallas Green, Matty Matheson, Tia Wood, Shaggy, Jully Black, Mustafa, Harland Williams, Leslie Liao, Caroline Rhea, the hosts of How Did This Get Made? – Live and more. Departure Festival + Conference takes place May 6-11 in Toronto.

Priority and Conference. Passes are on sale now at departureto.com.

“With each new addition, Departure continues to establish itself as a must-attend event for artists, industry leaders and fans alike,” said Kevin Barton, Executive Producer at Loft Entertainment. “From industry leaders to world-renowned performers, this year’s event will be essential for anyone passionate about the future of music, culture, and creativity.”

CONFERENCE PROGRAMMING:
Departure continues to grow its already impressive slate of speakers for this year’s conference, showcasing leaders and innovators from the music industry including Grammy-nominated, Juno-winning indie pop duo Tegan and Sara, Arkells frontman Max Kerman, who presents his debut book, Try Hard and multi-platinum award-winning pop-punk artist Fefe Dobson.

Offering key insights into the vigorous music market from talent management to industry insights, Departure’s Conference will welcome record producer Murda Beatz—known for his work with Travis Scott, Drake, and more; award-winning, multidisciplinary artist Vivek Shraya; Toronto journalist, author and publicist; Dalton Higgins; Indigenous Rights & Water activist, Autumn Peltier; Toronto-based realism and pop artist Julia Brevetti; co-host of TVO’s The Agenda, Nam Kiwanuka; vegan chef and creator Lauren Toyota, and Catherine Harrison, Founder and President of Revelios – Mental Health Works

Click here for a full list of Conference guests to date.

FESTIVAL MUSIC PROGRAMMING:
Departure will welcome additional musical talents to join the Festival including Canadian Folk Music’s Emerging Artist of the Year Noah Derksen, popular UK tech house DJ Chapter & Verse, rising star rapper DijahSB, emerging country artist Sully Burrows, electronic dance DJ Felix Cartal, who will headline an energetic DJ set outside Hotel X; and former frontman of the hip hop group Migos, rapper/singer Quavo and Murda Beatz will close the festival on May 11th, to cap off the week.

Click here for a full list of artists, venues and schedule of events to date.

FESTIVAL COMEDY PROGRAMMING:
Departure continues its celebration of Canadian comedy with the addition of Elvira Kurt, beloved host of the hit game show Spin Off, performing at Comedy Bar, a cornerstone of Canada’s comedy scene and a key Departure Festival venue. Additionally, actor and comedian Jamie Kennedy—known for his roles in the Scream movies, and The Jamie Kennedy Experiment—will join Harland Williams as a special guest for his two shows at The Royal Theatre on May 8th, adding even more star power to Departure’s comedy lineup.

Click here for a full list of comics, venues and schedule of events to date.

Hotel X Toronto serves as the central hub for Departure’s Conference activities and film screenings, while the Festival will span 40+ venues across the city and showcase 100+ emerging and established artists — with the complete lineup to be announced in the coming weeks.

#FIRSTLOOK: ADDITIONAL SPEAKERS, CREATIVES AND ARTISTS ANNOUNCES FOR DEPARTURE FESTIVAL

Loft Entertainment and Oak View Group (OVG) today announced its second wave of artists and speakers joining the inaugural Departure Festival + Conference. Participants announced include artists Dallas Green (City and Colour), Shad, Shaggy, Jully Black, top music industry commentator Bob Lefsetz and CEO of Hipgnosis Songs Fund Merck Mercuriadis will come together for a special fireside chat, among others who will be part of the Conference portion of the event. Joining this year’s Festival lineup are How Did This Get Made? – Live and comedy stars Trevor Wallace, Pete Holmes and Harland Williams. Departure will run May 6-11, 2025 in Toronto.

“The Departure lineup reflects the depth and diversity of creatives and industry leaders shaping today’s cultural landscape,” said Kevin Barton, Executive Producer at Loft Entertainment. “With top industry decision-makers in the room, our event is where careers will be launched and the next generation of talent gets discovered. We’re excited to roll out a showcase lineup featuring over 100 incredible artists, making Departure a true launch pad for emerging talent and a hub for meaningful connections. These collaborations will define the future of music while delivering world-class entertainment to the city.”

Hotel X Toronto will serve as the central hub for Departure’s Conference activities, while the Festival will span 40+ venues across the city and showcase 100+ emerging and established artists — with more to be announced.

Priority and Conference Passes are on sale now at departureto.com.

CONFERENCE PROGRAMMING
The latest wave of speakers and artists joining Departure’s Conference brings together an extraordinary lineup of musical creatives including Dallas Green (City and Colour / Alexisonfire / You+Me) and Shad. In a candid conversation, they’ll reflect on the 20-year journey of Sometimes, the album that launched Dallas’ solo career, and its impact as an independent success story through Dine Alone Records. Award-winning reggae legend Shaggy; Canada’s Queen of R&B Jully Black; multi-award-winning reggae DJ SPEXDABOSS; and visionary artist Justin Bua, best known for his paintings of musicians and DJs, also join the Conference lineup.

Offering invaluable insights into the evolving music market Departure’s Conference will also bring top music industry commentator Bob Lefsetz and CEO of Hipgnosis Songs Fund Merck Mercuriadis will come together for a special fireside chat; Wasserman Music Executive Tom Windish in conversation with Co-founder & CEO of ROSTR, Mark Williamson; renowned music executive and former SVP of Island Def Jam Music Group Johnnie Walker; EVP of Urban Catalogue at Universal Enterprises Katina Bynum; and Live Nation’s Head of Industry Relations Joey Vendetta.

Continuing to expand its footprint in the creative sector, Departure’s Conference will welcome renowned futurist and WAYE founder Sinead Bovell; the entertainment podcast Click and Tell hosts Sangita Patel and Carlos Bustamante; and social media powerhouse and Indigenous rights advocate Notorious Cree. Also, Rhiannon Rosalind, visionary Founder & CEO of Conscious Economics, and Aseel El-Baba, in-house Financial Therapist, will bring their bold approach to wealth and the new economy by leading an empowering interactive session featuring various artists.

Also joining the impressive lineup of speakers is NPR’s Tiny Desk Concert host Bobby Carter as part of the Radiodays North America programming previously announced here.

Click here for a full list of Conference guests to date.

FESTIVAL MUSIC PROGRAMMING:
Departure is proud to announce 100+ showcase artists across 40+ venues for this year’s Festival and debuts an exciting lineup of emerging artists. All Departure pass holders will have access to these showcases. The Music Pass is currently available at an early bird rate of $60 until April 1.

As part of the Artist Showcase, Departure will present the Canada’s Walk Of Fame RBC Emerging Musician Program Winner Showcase on May 7 at Rivoli, spotlighting rising talents Gabriel Fredette, Dallas, Mint Simon, Jackie Art, and Tiger Balme.

In addition, Departure has announced several premium events to join their roster including Noeline Hoffman, Sadboi, Planet Giza, Bobby Bazini, Koven Wei, PACKS, and Adam Melchor.

The SiriusXM Spotlight Series at Lee’s Palace, celebrating its 40th anniversary, brings prominent Canadian artists including Death from Above 1979, Noeline Hofmann, Planet Giza, Rural Alberta Advantage, and Papooz to the iconic venue.

Click here for a full list of artists, venues and schedule of events to date.

FESTIVAL COMEDY PROGRAMMING:
Departure’s laugh-out-loud comedy lineup will feature an impressive slate including How Did This Get Made? – Live, the award-winning podcast that celebrates bad movies with co-host comedians and actors Paul Scheer (The League), Jason Mantzoukas (Big Mouth), and June Diane Raphael (Grace & Frankie); viral stand-up comedian Trevor Wallace; stand-up comedian and actor Pete Holmes (Crashing); and beloved Canadian actor Harland Williams (Dumb and Dumber, RocketMan).

The Festival will place a specific focus on exceptional homegrown talents with two Canadian Comedy Industry Showcases, hosted by Ali Hassan and Rebecca Reeds that highlight some of the best Canadian comics, as well as the Canadian Headliner Series at Comedy Bar, which will welcome some of Canada’s most celebrated comics including acclaimed actress and comedian Caroline Rhea, stand-up powerhouse Mark Forward performing The New Show (where every performance is completely new), Juno Award-winning comedian Ivan Decker, and Indian-immigrant-turned-stand-up comedian Ashwyn Singh, among others, plus American comedian, actress, and writer Leslie Liao.

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.

Continuing to spotlight Canadian comedians, Departure will present 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.

In addition, Canadian comedy veterans Jean-Paul & Jay Martin will host the Trinidad vs. Jamaica Comedy Clash, where top Jamaican and Trinidadian comedians, including Team Jamaica: Julie Mango, Kathy Grant, and Fancy Cat, and Team Trinidad: Jr. Lee, Ro ‘Dey, and a surprise special guest go head-to-head in a clean comedy showdown.

Click here for a list of Comedy Programming to date.

#FIRSTLOOK: DEPARTURE FESTIVAL + CONFERENCE 2025 LINEUP ANNOUNCEMENT

Loft Entertainment and Oak View Group (OVG) today unveiled its first announcement of artists and speakers stemming from music, art, comedy and tech who are confirmed to attend the inaugural Departure Festival + Conference from May 6-11, 2025 in Toronto. These creatives include music luminaries Bryan Adams, Mustafa, Tia Wood, and Death From Above 1979; renowned restaurateur Matty Matheson; platinum record producer T-Minus in conversation with Brian “B.Dot” Miller; influential figure and innovator in the sports and entertainment industry Tim Leiweke, Chairman & CEO of Oak View Group (OVG); tech thought leader Matt McGowan, GM of Snap Inc. in Canada; and reputable crisis communications expert Molly McPherson. Together, these creatives exemplify the very best of their respective crafts, achieving massive success domestically and abroad. A groundbreaking new partnership with Elevate, Canada’s most influential tech and innovation event, adds to the conference’s dynamic programming.

A reimagined and expanded vision of Canadian Music Week (CMW), Departure is a dynamic and innovative launchpad bursting with diverse talent, audience favourites, and modern creative industry thinkers. While Hotel X Toronto, the urban resort on the Lake Ontario Waterfront, will serve as Departure’s host hotel, the global event will reach audiences across Toronto with concert venues in every corner of the city. A stream of notable speakers, artists and must-attend events will continue to be revealed over the coming months. Priority and Conference passes are on sale now at departureto.com.

“Our first edition of Departure is about honouring our roots in music and growing into other creative spaces while fostering the relationship between artist and industry,” said Kevin Barton, Executive Producer at Loft Entertainment. “This year’s lineup showcases a wealth of established and emerging talent from across the country and beyond, creating opportunities for meaningful dialogue, sharing innovative ideas and building deeper connections within Canada’s dynamic arts community. We look forward to sharing more programming announcements in the weeks to come.”

“With its vibrant cultural scene, Toronto is the perfect home for the Departure Festival + Conference,” said Tom Pistore, President of Oak View Group Canada. “We look forward to bringing together the most diverse and talented group of artists, innovators, and industry leaders to create a launchpad for the next wave of music, art, tech, and comedy.”

The Conference portion is where industry professionals from Canada and abroad will come together as a community to share ideas, inspire one another and connect to build a vibrant creative future. The Festival portion of the weeklong event is where audiences can enjoy musical performances by their favourite artists, comedy sets from some of North America’s funniest people and culinary experiences from top chefs.

CONFERENCE PROGRAMMING TO DATE:

Industry Experts:
Departure’s robust lineup of powerhouse speakers highlights individual streams within the creative space, welcoming Canadian chef, restaurateur and actor/executive producer of the Emmy Award-winning hit show The Bear, Matty Matheson; legendary music superstar Bryan Adams in collaboration with Radiodays North America; leader and veteran in the sports and entertainment industry Tim Leiweke, Chairman & CEO of Oak View Group (OVG); Grammy-nominated record producer T-Minus; one of music journalism’s most revered voices and viral Rap Radar Podcast co-host, Brian “B.Dot” Miller; Emmy award-winning music supervisor Matt Biffa who has worked on Sex Education, Hacks, and Harry Potter; and renowned photographer and creative director Danny Hastings, who has worked alongside some of the biggest names in the music industry.

Incorporating a wider spectrum of artistic expressions, the Conference will also include trailblazer and advocate for Indigenous voices Shayla Stonechild and internationally recognized crisis communications expert Molly McPherson.

“Toronto has helped me build a beautiful community I can always come back to and has deepened my love for food,” said Matty Matheson. “Toronto is a perfect place to discover something new and really dive in head first. Departure reminds me of those feelings for Toronto; where we thrive on creativity and culture and all the people who make this city special.”

Radiodays North America:
Taking place May 6 – 8 at Hotel X, ​Radiodays North America is the premier conference for radio, podcasting, and digital audio professionals, Radiodays will feature inspiring speakers about the latest trends and strategies shaping the future of audio. More programming details to be announced in the coming weeks.

Tech:
Diving into the future of technology, Departure will feature leaders in the tech space including General Manager of Snap Inc. in Canada, Matt McGowan, President of Visibility Media and former Global Head of Riot Games Music Toa Dunn, and the Co-Founder and CEO of Elevate, Lisa Zarzeczny.

Bridging the gap between tech and entertainment, Departure will also be joining forces with Elevate, Canada’s most influential tech and innovation event. Elevate is a non-profit that unites world-class innovators to catalyze transformation in the Canadian tech ecosystem. Elevate has hosted global icons such as First Lady & Author Michelle Obama, Businesswoman & TV personality Martha Stewart, and Former Google CEO Eric Schmidt.

Film:
Continuing to celebrate the power of music, Departure will host special film presentations including Alex Ross Perry’s (Golden Exits, Her Smell) latest film Pavements (MUBI) about the iconic ’90s indie band Pavement starring Jason Schwartzman​ and Joe Keery. More film programming will be announced in the coming weeks.

FESTIVAL PROGRAMMING TO DATE:

Departure will present Music and Comedy Showcases available to all pass holders, along with Premium events that require the purchase of separate tickets. The Comedy Showcase lineup will be announced in February and the Music Showcase following in March.

Music:
With lively performances across the city from Meridian Hall to History, The Drake Hotel and more, Departure will feature some of the most sought-after artists making waves today. The Premium events include multi-award winning powerhouse Mustafa; groundbreaking soulful performer Tia Wood; punk rock duo Death From Above 1979 performing for two nights at Lee’s Palace celebrating the 10th Anniversary of their album The Physical World; R&B visionary Avenoir; French pop duo Papooz ; indie rockers Rural Alberta Advantage; genre-defying duo Freak Heat Waves; celebrated singer-songwriter Bria Salmena; and burgeoning Brooklyn-based punk band YHWH Nailgun; with more to be announced.

Ensuring audiences experience the full breadth of Toronto’s bustling cultural scene, Departure will extend across the city with special events at Stackt Market, The Well and a 40th anniversary celebration of Lee’s Palace. More information on those events to be shared in the coming weeks.

Highlighted Premium events include:
Mustafa – May 6 @ Meridian Hall
Avenoir – May 6 @ Axis Club
Rural Alberta Advantage – May 7 @ Lee’s Palace
Freak Heat Waves – May 7 @ Dance Cave
Death From Above 1979 – May 8 & 9 @ Lee’s Palace
Bria Salmena – May 9 @ The Great Hall
Tia Wood – May 9 @ The Drake Hotel
YHWH Nailgun – May 9 @ Bovine Sex Club
Papooz – May 11 @ Lee’s Palace

Comedy:
With more than 40 years of shaping the comedy landscape, Bruce Hills, the former president of Just For Laughs, has joined as the Executive Producer of Departure Comedy. Renowned for uncovering and fostering the talent behind some of the biggest names in comedy today, Hills’ focus will be on curating an impressive comedy slate, conference and spearheading the Canadian industry showcases for the festival.

From intimate spaces to large theatres, the festival’s comedy programming will be in iconic venues around the city including Meridian Hall, Comedy Bar, The Second City Toronto, and Queen Elizabeth Theatre – all of which will come alive with laughter as they host acclaimed stand-up comedians.

In the coming weeks, Departure will unveil its 2025 comedy and conference lineup and a number of Canadian industry showcases which will include Don’t Tell Comedy, the # 1 global discovery platform for stand-up comedy, who will bring their premier stand-up showcase to Toronto at a secret and unique location, while spotlighting incredible Canadian talent. Don’t Tell Comedy’s Tapings are a global phenomenon, the clips garner over an astonishing 1.2 billion views annually.

More details on the Departure comedy programming to be announced.

Additional guests and events will be announced in the coming weeks. For more programming and ticketing info, visit departureto.com.