Play It Loud! star Jay Douglas tops the bill at Jaymz Bee's epic Caravan of Music fundraiser at the Old Mill on Monday night.
Jaymz Bee's Caravan of Music
Jaymz Bee has spent the past decade turning his birthday into a fundraising celebration, raising tens of thousands for various charities. For the past several years, he has raised funds for the Unison Fund, a non-profit music industry organization providing counselling, emergency financial support, and other resources to the Canadian music community.
Monday, April 13, 2026 marks his biggest event yet: 24 bands and over 140+ musicians performing in 12 unique rooms at the iconic Old Mill Toronto, all in one unforgettable night.
The Caravan of Music is a four-hour event where hundreds of people tour the historic Old Mill, catching a few songs in each room, from intimate 100-person spaces to 300-capacity venues.
Each ticket (a passport) grants you full access to enjoy over 140 musicians in one evening, spanning various genres: jazz, funk, soul, blues, country, singer-songwriters, and an 18-piece big band. From solo artists to full ensembles, there's something for every music lover. Confirmed lineup includes Jay Douglas (see below), Genevieve Marentette, George Koller, Jane Bunnett and Danae Olano, Drew Jurecka, Eliana Cuevas and Jeremy Ledbetter, Adam James, Alexis Baro, Alison Young, Ben Wittman, Blackburn Brothers, Brendee Green's Poetry Brothel, Chris Bottomley's Brainfudge, Denielle Bassels, Dizzy and Fay, Eric St-Laurent, Ewen Farncombe, Mark Kelso, Melissa Payne, Michael Shand, Robert Priest, Roger aka Roger, Ross MacIntyre, Sam Broverman, Sean Nykwist, Swing Shift Big Band, Taylor Abrahamse, The Roncy Boys, The Shuffle Demons, Tony Quarrington, Whitney Ross Barris, and more to come!
Caravan participants will have a map, along with their passport ticket, to help them find the various live music rooms: The Westminster Room, Drawing Room, Garden Room, Balmoral Room, Humber Room, Victoria Room, York Room, Mill Room, Main Dining Room, The Chapel, and more!
Get tickets right here. Watch a few performances by Jay Douglas, Jane Bunnett & Danae Olano and Genevieve Marentette below.
Jaymz Bee's Caravan of Music
Date: Monday, April 13th
Venue: Old Mill Toronto, 21 Old Mill Rd
General Admission Tickets: $55 +HST / $60 +HST at the door
VIP Gala Dinner: $250 +HST - An intimate evening before the Caravan begins, includes a three-course meal with wine courtesy of Henry of Pelham and Peninsula Ridge Estates, all-star house band with special guest performances, and full Caravan access following dinner.
The electrifying Jay Douglas – subject of the Play It Loud! documentary – hits the Old Mill with his all star band on Friday at 8 pm.
Toronto, get ready for an unforgettable evening with Jay Douglas — three-time Juno nominee, legendary bandleader, producer, and one of Canada’s most beloved and charismatic Island soul ambassadors.
From Rastafest to the 4 Seasons Reggae Cruise, Jay has lit up stages around the world. He’s collaborated with icons like Beres Hammond, Freddie McGregor, Marcia Griffiths, Luciano, Ken Boothe, Ziggy Marley, and the legendary Ernest Ranglin.
Beyond the music, Jay’s heart is in the community — including helping bring Reggae Lane to life in Toronto.
As can be seen in Graeme Mathieson's excellent documentary, Play It Loud! How Toronto Got Soul (check it out here here), Jay's music career in Toronto began as the frontman of The Cougars, who ruled the local Caribbean club scene in the 60s and showcased at Toronto's inaugural Caribana Festival in 1967.
And now he’s bringing that timeless magic to The Old Mill (21 Old Mill Rd) this Friday (November 21) from 8 pm to 10 pm. Tickets are $30, available online at www.oldmilltoronto.comor call 416-207-2020 for reservations. Don’t miss this night of soul, storytelling, and pure good vibes.
Watch a CBC interview with Jay followed by a couple of recent performances below.
Don't miss Toronto's own Jay Douglas, star of the Play It Loud! documentary and the Jamaica To Toronto comp , tearing up The Redwood Theatre on April 12.
Catch Jay Douglas & The All Stars feat. drummer Everton "Pablo" Paul live at The Redwood Theatre on Saturday, April 12th, still buzzing off the acclaimed documentary "Play It Loud: How Toronto Got Soul" celebrating Jay’s iconic career and the rise of soulful Jamaican music in Canada. This is a show you won’t want to miss! Get tickets right here. Check the clips below.
Jamaica To Toronto keyman Jay Douglas is appearing at Sonic Boom on Friday (6 pm) followed by a full show at The Drake Hotel on Saturday (February 15).
Here's the scoop...
Back from a successful west coast swing promoting the great new feature-length documentary Play It Loud! How Toronto Got Soul with director Graeme Mathieson, the film's star Jay Douglas is looking forward to returning to the stage in Toronto – despite the chilly temps – for a Valentine's Day warm-up. While some performers choose to hibernate during the winter months in the Great White North, Jay Douglas is clearly made of sterner stuff.
"We just flew in from the Yukon," say Jay, "where we had a screening of Play It Loud! at the Available Light Film Festival in Whitehorse. It was well accepted by the audience there and other than the bitterly cold weather, everything worked out great!"
Later today he'll be singing a set of lover's rock for a free in-store at Sonic Boom (215 Spadina) starting at 6 pm to coincide with Light In The Attic's timely vinyl repress of the Jamaica To Toronto 2LP anthology and follow it up with a full show at The Drake Hotel on Saturday (February 15) backed by his longtime pal, dynamite drummer Everton "Pablo" Paul and crew. The doors open at 9:30 pm and tickets are $17.31 available right here.
Check out a short clip of Jay's version of "I Wish It Would Rain," the trailer for "Play It Loud!," a video chat about the documentary with Rudy Blair along with some performance footage.
Trailblazing Toronto soul great Jay Douglas tells his story in Play It Loud! screening at Hot Docs Theatre on December 4th & 7th.
Here's the scoop...
It’s official! PLAY IT LOUD! How Toronto Got Soul is having its WORLD PREMIERE at the Hot Docs Theatre, 506 Bloor St W., on December 4th at 6:30 p.m. (now sold out), with a second screening on December 7th at 8:00 p.m.
Play it Loud! – How Toronto Got Soul is a feature documentary that tells the little known story of how Jamaican music became a critical and unlikely part of Canadian culture. The film reveals a social and cultural migration that made Canada a mecca for Jamaican music, recognized around the world, but little heralded at home. We tell This story is told through the life, music, struggles and triumphs of beloved Jamaican Canadian singer Jay Douglas. Born as Clive Pinnock, in rural Jamaica to a single mother, Douglas began performing professionally at 17 and has never stopped. Today, nearly sixty 60 years later, he’s more popular than ever.
Douglas’ life mirrors the emergence of Jamaican popular music, both in its birthplace, and his adopted country. He’s a witness and participant to the birth of ska and reggae, the Jamaican diaspora in the UK and Canada, and the emergence of a uniquely Canadian Black music culture. Through Jay’s personal story, the film will tell an important and largely unknown tale of cultural transformation.
The Wednesday, December 4 screening will be followed by a Q&A with director Graeme Mathieson, musician Jay Douglas and producer Andrew Munger. The Saturday, December 7 screening will be followed by a Q&A with director Graeme Mathieson and Everton "Pablo" Paul, featured in the film. Both sessions will be moderated by Heather Haynes, Hot Docs' Director of Programming. Watch the trailer below.
Jamaican-born, Toronto-based soul great Jay Douglas stars in Graeme Mathieson's forthcoming film Play It Loud! Check the trailer.
Here's the scoop...
Early 1960’s Toronto was a mostly white, Anglo-centric city. Beneath this veneer of Conservative respectability, an exciting underground music scene emerged, created by a Jamaican diaspora including newcomers like Jackie Mittoo, Wayne McGhie and a teenageJay Douglas. Battling racism and indifference, they made an indelible, but little appreciated mark on Canadian music and culture. Six decades later, Jay Douglas is still carrying the torch for Jamaican music, and enjoying the recognition and respect he has long craved.
Play it Loud! (set for release via TVO Docs in February, 2025) is a feature documentary that tells the little known story of how Jamaican music became a critical and unlikely part of Canadian culture. The film reveals a social and cultural migration that made Canada a mecca for Jamaican music, recognized around the world, but little heralded at home. This story is told through the life, music, struggles and triumphs of beloved Jamaican Canadian singer Jay Douglas. Born as Clive Pinnock, in rural Jamaica to a single mother, Douglas began performing professionally at 17 and has never stopped. Today, nearly 60 years later, he’s more popular than ever.
The fiery Irene Torres and soulful Jay Douglas top the cast of 24 artists performing at Jaymz Bee's fundraiser tonight starting at 8pm
JAYMZ BEE'S CARAVAN OF MUSIC
The Old Mill (21 Old Mill Rd., Toronto)
Thursday, April 11th
Time: 8:00 PM - 12 Midnight. Doors at 7:30 pm.
General Admission: $40 advance ($50 at the door). Get tickets here.
Jaymz Bee's Caravan of Music, an all-night extravaganza at Toronto's historic Old Mill featuring 24 artists performing in 12 different rooms, all in support of the Unison Fund. Over 100 musicians in total!
Jaymz Bee has spent the past decade celebrating his birthday by raising funds for various charities and for the past several years has raised funds for The Unison Fund (https://unisonfund.ca), a Canadian charity that assists those in the music industry in times of crisis. Bee was on its board of directors for years and has raised tens of thousands from his parties.
This year's event will be the biggest yet – 24 bands performing in 12 rooms at Old Mill Toronto to raise money for The Unison Fund, a non-profit music industry charity that provides counselling, emergency financial support, and other resources to the Canadian music community.
Jaymz Bee’s Caravan of Music is a four-hour event where hundreds of people tour the various rooms at Old Mill Toronto, taking in a few songs from each band. Tickets (a passport) are $40 each, with 100% of the door going to The Unison Fund, and access to all of the rooms. You can enjoy over 100 musicians in one evening, performing various styles of music. See the event map below.
Caravan participants will have a map, along with their passport ticket, to help them find the various venues: The Westminster Room, Drawing Room, Garden Room, Balmoral Room, Humber Room, Victoria Room, York Room, Mill Room, Main Dining Room and The Chapel and more! The evening will end at midnight - but will continue in the main dining room for those who don’t feel like going home just yet.
Jay Douglas highlights a salute to Toronto's Caribbean music legacy at TD Music Hall (178 Victoria) on Saturday at 8 pm.
THE SOUND OF RHYTHMS & RESISTANCE
featuring: JAY DOUGLAS, NANA McLEAN, AMMOYE & KAiRO McLEAN
house band: THE HUMAN RIGHTS
with Rayzalution & DJ Chocolate
MC Carrie Mullings
SATURDAY NOVEMBER 4
at TD MUSIC HALL
178 Victoria Street, Toronto
8pm doors
$30 (plus charges) advance. Get tickets from TD Music Hall here.
The Sound of Rhythms and Resistance builds on the Toronto Music Experience’s acclaimed exhibition at Friars Music Museum (which was produced in association with the Downtown Yonge BIA) in celebrating the rich legacy of reggae in Toronto. Audiences will hear music from the originators who came here from Jamaica in the 1960s and 70s through to today's innovators. The evening will feature much-loved veteran artists Jay Douglas and Nana McLean and contemporary stars Ammoye (7-time JUNO nominee) and 2-time JUNO winner Kairo McLean, all backed by our house band, The Human Rights. The opening set will be by all-female band Rayzalution, with DJ Chocolate and MC Carrie Mullings.
ABOUT THE ARTISTS
Jay Douglas
Jay Douglas is a 3-time JUNO award nominee, music producer and bandleader of the Jay Douglas All-Star Band and performed in the first Caribana parade in 1967 as a member of The Cougars. He has performed at various festivals worldwide, including Rastafest in Toronto and the 4 Seasons Reggae Cruise in Atlanta, Georgia. He has worked with international reggae stars such as Beres Hammond, Freddie McGregor, Marcia Griffiths, Luciano, Ken Boothe, Leroy Sibbles, Sly Dunbar, General Trees, Ziggy Marley, Lynn Taitt and guitar great Ernest Ranglin. Jay played a crucial role in Light In The Attic's important Jamaica To Toronto anthology and their 2004 reissue of the classic Wayne McGhie & The Sounds Of Joy album. Jay has been involved in a great deal of community work including working with Councillor Josh Colle to establish Reggae Lane in Toronto. Listen to Jay's new Sly Dunbar-produced single, "The World Is Troubled" featuring Tasha T (below).
Nana McLean
Nana McLean recorded her debut single in 1977 at Studio One for legendary producer Clement Coxsone Dodd, with a rendition of the Everly Brothers' classic ‘Till I Kissed You’ (listen below). After four decades, she is still one of reggae music’s premier artists and proudly wears the crown as the Queen of Reggae in Canada. On any given day, you can find Nana still busy in the studio recording songs as she has been doing for many years. She still receives calls from many notable producers who want to capture her unique and sweet vocals and potent lyrics on their latest riddims. Popular music selectors still reach out for dubplates of some of her biggest hits.
Ammoye
Singing songs of love, life and justice, 7-time JUNO nomine Ammoye delivers a wholly unique future forward reggae sound that incorporates old-school rocksteady dancehall and dubstep, with gospel, soul and R&B. With her infectious voice and messages of empowerment, Jamaican-born Ammoye is a lightworker and self declared soul rebel. Ammoye’s newest 13-track album Water features a who’s who of the contemporary international reggae scene with production from Jamaica’s Tandra Lytes Jhagroo and Natural High, Toronto’s own DJ Agile and Danny Maestro, The Senior Allstars from Germany, Thomas Blondet from Brooklyn, Adian Hanson Donsome of NYC’s Donsome Records and the legendary Lord SassaFras.
Kairo McLean
Winner of two consecutive JUNO Awards at the age of 14, Kairo McLean was two years old he began to show an interest in music and by the time he was 3 he was already playing drums. At 5 he picked up the acoustic guitar and by 6 he was already singing and performing at festivals. To call this child a natural would be an understatement. Kairo is a true scholar of reggae music. He is deeply familiar with all the artists in the genre, past records, musicians, producers and sound systems, details that only the most studied connoisseur of reggae would know. When it comes to his own compositions, Kairo is as “old school” as it gets, drawing influence from Peter Tosh, Dennis Brown and Gregory Isaacs.
The Human Rights
Since they came together in 2007 around one of the Toronto reggae scene’s true lions, Friendlyness (Big Sugar, Culture Shock, Truth And Rights), The Human Rights have become one of the most beloved and respected Canadian independent reggae bands. In 2014, our longtime bredren Tréson joined the band to give them a uniquely powerful two-man vocal front line that delivers roots reggae, soul, R&B and dancehall vibes. They have played over 200 club and festival shows across Canada, and earlier this year toured the United States for the first time; and will be playing at the New Orleans Reggae Festival this October.
Rayzalution
This all-female reggae band draws influences from greats such as Bob Marley, Marcia Griffiths, Third World, Morgan Heritage, Chronixx & Zinc Fence Band, Beres Hammond, Buju Banton, Destiny’s Child, and En Vouge. With powerful vocals they combine heavenly harmonies with exceptional musicianship and dynamic performances, the band promotes positivity and spreads a conscious message while still having a good time entertaining the audience. The band has shared the stage with international reggae acts such as: Maxi Priest, Freddie McGregor, Baby Cham, Shanchez, Romain Virgo, Dexta Daps, Mikey Spice, Beenie-Man, I-Wayne, Razor B, Marcia Griffiths, Lady G, Sister Nancy and the Mighty Diamonds to name a few.
DJ Chocolate
Whether it’s playing music, working as a lawyer, furthering this business of music with her two
companies or at the controls and decks of her radio show, DJ Chocolate never sleeps! Chocolate has been sharing the vibes on stage and on radio and at parties and concerts across North America for over thirty years alongside greats from the reggae and jungle world, including Burning Spear, Luciano, the second-generation Marleys, Sly & Robbie, Meta and the Cornerstones, Exco Levi and countless others. Most recently, she joined a well-known sound crew based in the US. Jamaica and Barbados called Hardcore International Music.
MC Carrie Mullings
Born into a musical family, Carrie Mullings was surrounded by the sounds of reggae music from an early age. Her father, the late Karl Winston Mullings, was a pioneer of the Jamaica to Toronto musical explosion and shared his gift with Carrie and her younger sister, Tanya. For over two decades, Carrie Mullings has been a force to be reckoned with in the Canadian music and media industries. She has contributed immensely to the growth and development of the Canadian reggae music infrastructure, bringing the genre into the forefront of worldwide recognition and reception. Celebrating her 20th year in radio broadcasting, Carrie continues to empower the community by sharing and uplifting through the airwaves.
The soulful Jay Douglas will be singing blues and R&B songs from his Confession album tonight at Lula Lounge. Doors at 7 pm.
Here's the scoop...
Drawing inspiration from his roots in Jamaica and Canada, Jay Douglas has developed a wide-ranging repertoire of American blues, West Indian rhythms, and jazz standards. Over the past 10 years, Jay Douglas has performed around the world and at annual Toronto events such as the Beaches Jazz Festival, Jerk Fest, Yonge and Dundas Square, and a Taste of Lawrence. Some of his major hits include tracks like “Messengers”, “Man to Man”, “What Will My Mary Say”, “I Don't Wanna Cry”, and “Lovers Paradise.”
In 2006, Jay Douglas was proclaimed the winner of NOW Magazine's Toronto's "Best R&B Act" and in 2007, he won the "Male Reggae Vocalist of the Year" at the Annual Toronto Reggae Awards. Recently, his album “Lover’s Paradise” won "Reggae Recording of the Year" at the 2012 JUNO Awards and was the recipient of the "G98.7 FM Entertainment Award" at the Harry Jarome Awards as well!
SPECIAL GUEST ROBIN BANKS
Just a country girl with big city ways", is how Robin Banks describes herself. An electrifying performer, a sultry and powerful vocalist best known for her blues and jazz depth and authenticity. Banks is an artist, a songwriter, a music producer and band leader who dug up her Canadian roots and transplanted them into a spicy music life in Texas but also in Jamaica performing in tourism entertainment. She writes catchy, clever songs of life and love and records them with some of America's most prominent musicians and producers. Don't miss this opportunity to catch her live -- she is the real deal!
The Lula Reggae & Blues Revue
with Jay Douglas & His All-Star Band and guest Robin Banks
Soulful Toronto reggae great Jay Douglas proves he's equally adept at singing the blues with "I'm In Love With You"
Here's the scoop...
Following the release of a string of reggae singles, including “Stone In Love With You,” “Muschange,” and “Pattidemic,” Jay Douglas slows things down and takes a stroll down the bass line to deliver a smashing blues single – “I’m In Love With You.”
Jay Douglas has always had a strong connection with blues and jazz, which shows throughout this icon’s catalog. What makes “I’m In Love With You” special is its ability to transport the listener to a time when big bands were the norm and warmly embraced. Warm brass swells and slick guitar riffs draw the listener in, reminiscent of the appeal of jazz bars back in the 60s.
“I’m In Love With You” is brimming with rich layers of instrumentation – even on multiple listens it’s hard to narrow a definitive list. That’s always been the appeal of Jay Douglas, and he doubles down on this musical prowess here in his newest single.
“Many years ago, a promoter allowed me to put a band together for a famous blues singer from the USA whose name is Rosco Gordon. His music is one of the main reasons we're enjoying reggae music today. Working with Rosco gave me so much inspiration for my blues recordings. “I'm in Love With You” was produced by the maestro Eddie Bullen – lending to that blues style.”
Jay Douglas’ ability to connect with listeners and paint a picture with his lyrics is truly something special and always humbling. Growing up in Jamaica, Douglas was drawn to blues, jazz, gospel, country, mento, and calypso styles of music early on. He draws much of his inspiration from this love affair he has with these genres and writes music he loves that he believes will love him back.
“Writing my music gives me a platform to share the truth and experience of my musical journey with others. The idea behind my music is all about the truth, and good vibrations for our souls. Just moving and grooving. The connections between me, my instruments, bandmasters, and collaborators - it's a love affair under one foundation to share with the younger generations who are the gems of the future.”
Jay Douglas found his introduction to the limelight in Montego Bay, Jamaica. From there, his natural charisma and irresistible charm have led to a successful and continuing 45+ year career in entertainment, through which he has developed a passion for American Blues, West Indian Rhythms, and Jazz Standards.
Douglas’ tactile and impactful performances are the reason he was announced the winner of NOW Magazine’s “Toronto’s Best R&B Act” in 2006 and Toronto Reggae Awards “Male Reggae Vocalist Of The Year” in 2007. These accolades drew the attention of Seattle-based Light In The Attic, choosing Douglas as the Headliner of the “From Jamaica to Toronto” tour.
More recently, Douglas was nominated for “Reggae Recording of the Year” at the 2012 JUNO Awards and was the recipient of “G98.7 FM Entertainment Award” at the Harry Jarome Awards. His most recent nomination was for his collaboration with General Trees on “Jah Children,” receiving his second JUNO nomination during 2020.
Jay Douglas’ connection to his homeland has been the foundation of his career, which has led Douglas’ to form lifelong friendships and musical collaborations with many of the founding musicians of ska, rock steady, and reggae. His upcoming single teasing his new album is set to feature a collaboration with one of his old friends, the legendary guitarist Ernest Ranglin who just celebrated his 90th birthday.
Listen to “I’m In Love With You” below. Stream it on Spotify right here.
