| A soul-stirring performance by Jay Douglas will be the highlight of Blues Mondays at Union Station today at 5:30 pm. |
Monday, July 20, 2026
Play It Loud! star Jay Douglas plays Blues Mondays @ Union Station, July 20
Monday, April 13, 2026
Jaymz Bee's Caravan of Music feat. Jay Douglas and many more @ The Old Mill, Monday
| 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 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.
Doors: 7:30 PM
VIP Gala Dinner: 6PM-8PM
Caravan of Music: 8 PM-12 midnight
Friday, November 21, 2025
"Play It Loud!" star Jay Douglas lights up the Old Mill, Friday
| 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.com or 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.
Sunday, November 16, 2025
Jamaica Relief Benefit w/ Jay Douglas, Carl Harvey and others @ El Mocambo, Sunday
| Jay Douglas, who maintains a close connection to his Montego Bay roots, joins Maytals guitarist Carl Harvey for Jamaica Relief Benefit at 4 pm. |
| Get tickets for the "One Love, One Heart" Jamaica Relief Benefit in support of the Helping Hands Jamaica Foundation right here. |
Thursday, August 21, 2025
T.O. soul legend Jay Douglas & reggae great Luciano @ CNE Bandshell, Aug 21
| Don't miss this stellar double bill of Jay Douglas (7:30pm) and Luciano (8:30pm) at the CNE Bandshell tonight. Check the clips. |
CNE Bandshell line-up
Thursday, August 21 – Luciano & Jay Douglas
Friday, August 22 – July Talk w/ The Darcys
Saturday, August 23 – 98 Degrees w/ Alyssa Reid
Sunday, August 24 – The Commodores with Jully Black
Monday, August 25 – Cold War Kids
Tuesday, August 26 – Bishop Briggs
Wednesday, August 27 – The Dirty Nil w/ Ben Quad
Thursday, August 28 – The Rural Alberta Advantage w/ Special Guest Yukon Blonde
Friday, August 29 – Marianas Trench w/ Nicolina
Saturday, August 30 – Dean Brody
Sunday, August 31 – Soca Night ft. GBM Nutron, Mical Teja, Coutain, with DJ Ana, Ultra Simmo and Dr. Jay
Monday, September 1 – No concert on Labour Day
Saturday, April 12, 2025
Jay Douglas All Stars hit The Redwood Theatre, April 12
| 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. |
The Redwood Theatre (1300 Gerrard St. East)
Saturday, April 12
Doors 7pm | Show 8pm–11pm
Tickets: $40–$60 and selling fast!
Grab yours now at https://www.theredwoodtheatre.com/
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.
Tuesday, April 8, 2025
Jaymz Bee's Caravan of Music fundraiser @ The Old Mill, Wednesday
| Irene Torres, Jay Douglas, Tia Brazda, Jessica Stuart and other T.O. performers join Jaymz Bee at The Old Mill on Wednesday. |
Friday, February 14, 2025
Jay Douglas sings lovers rock for Valentine's Day at Sonic Boom, Friday
| 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...
Tuesday, December 3, 2024
Play It Loud! How Toronto Got Soul premieres at Hot Docs Theatre Dec. 4th
| 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.
Tickets for the December 7th show are available right here: https://hotdocs.ca/whats-on/films/ds-play-it-loud
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.
Find out more about the film and upcoming screenings at: https://www.playitlouddoc.com/
Wednesday, November 20, 2024
Toronto soul great Jay Douglas @ Old Mill Jazz Lounge, Friday
| Jay Douglas – featured in the new Play It Loud! documentary – performs two sets at the Old Mill on Friday at 8 pm sharp. |
| The new documentary Play It Loud! screens at the Hot Docs Cinema on Dec 4th and 7th. Get tickets here. |
Monday, October 28, 2024
Jay Douglas featured in Play It Loud! doc on Toronto's Jamaican connection
| 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.
For more info, clips and theatre screening dates, check the site: https://www.playitlouddoc.com/
Watch the Play It Loud! trailer below.
Sunday, August 4, 2024
From Jamaica To Toronto with Jay Douglas & doc preview at Harbourfront, Sunday
| Jay Douglas tears up at Harbourfront Centre at 9:30pm following a preview of the Sounds & Pressure T.O. reggae doc at 6:30pm. |
| The new doc series Sounds & Pressure: Reggae In A Foreign Land has a preview screening at 6:30pm. Get tickets here. |
Thursday, April 11, 2024
Irene Torres & Jay Douglas light up Jaymz Bee's Caravan Of Music @ Old Mill, tonight
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| 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.
Thursday, November 2, 2023
The Sound of Rhythms & Resistance w/ Jay Douglas, Nana McLean @ TD Music Hall, Nov 4
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| Jay Douglas highlights a salute to Toronto's Caribbean music legacy at TD Music Hall (178 Victoria) on Saturday at 8 pm. |
Friday, October 20, 2023
Jay Douglas at the Old Mill's Jazz Lounge, Friday
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| Check out the soulful Jay Douglas at the Old Mill's Jazz Lounge tonight. Doors open at 6 pm and showtime is at 8 pm. |
Saturday, August 19, 2023
T.O.'s Jay Douglas joins reggae great Marcia Griffiths @ CNE Bandshell, August 24
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| Toronto's own Jay Douglas shares the stage with Marcia Griffiths at the CNE Bandshell on Thursday at 7:30 pm. |
![]() |
| The always entertaining Jay Douglas opens the show at 7:30pm followed by Jamaican reggae legend Marcia Griffiths at 8:30pm. |
Saturday, July 22, 2023
Jay Douglas and the All Stars light up Woodbine Park, Saturday
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| Jay Douglas and the All Stars top the Beaches Jazz Fest line-up at Woodbine Park (1695 Queen St. East) tonight at 9 pm. |
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| For more Beaches International Jazz Festival 2023 info, check the site right here. |
Wednesday, November 16, 2022
Jay Douglas & Robin Banks @ Lula Lounge, Wednesday
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| 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...
Friday, June 24, 2022
Versatile Jay Douglas sings the blues with "I'm In Love With You"
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| 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.
Sunday, July 5, 2020
Watch the Jay Douglas video for "Jah Children" feat. General Trees
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| Soulful Toronto singer Jay Douglas is joined by dancehall don General Trees for "Jah Children" which should've won a Juno. |
Tone Rangers' Tuesday Bluegrass Club @ Bell & Beacon, August 4
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