Divine Brown reflects on reimagining pop icons at UnCovered: Madonna & Cher, tracing the soulful journey that shaped her voice, storytelling, and her place in Toronto’s creative community.
In this episode of Afropolitan Dialogues, Toronto’s own Divine Brown joins us for a deep, soulful conversation that travels from Koerner Hall to the underground studios of Toronto’s neo-soul era. Fresh off headlining UnCovered: Madonna & Cher with The Musical Stage Company, Divine shares how she approached reimagining anthems like “Like a Prayer” and “Believe” through a theatrical, soul-infused lens.
Along the way, she takes us back to 2005 and the making of her debut album Divine Brown, remembers late nights in the studio with Socrates, James Bryan, and a young Noah “40” Shebib, and speaks candidly about how D’Angelo’s Brown Sugar shaped her artistic path. The conversation also explores her celebrated docu-concert Billie, Sarah & Ella: Revolutionary Women in Jazz, the role of storytelling across music, theatre, and film, and the fierce creative energy that Toronto—and its Black and Caribbean communities—continue to pour into her work.
Conversation highlights
- Divine’s experience headlining UnCovered: Madonna & Cher and bringing a theatrical soul sensibility to pop classics.
- The collaborative process with music supervisor Kevin Wong and the freedom to shape her own interpretations.
- Memories from the 2005 Divine Brown album era, including working with Socrates, James Bryan, and Noah “40” Shebib.
- How D’Angelo’s Brown Sugar moved her to tears and inspired her commitment to authentic soul expression.
- Why storytelling sits at the centre of everything she does, from gospel choir to Soulpepper Theatre to screen work.
- A reflection on the genre-blending magic of the 1980s versus today’s more homogenized pop landscape.
- Creating and performing Billie, Sarah & Ella: Revolutionary Women in Jazz and honouring jazz icons who shaped her.
- The creative ecosystem of Toronto, mentorship from Jackie Richardson, and pride in Black Canadian and Caribbean roots.
- Navigating family expectations as a young Caribbean creative and leaving home at 17 to follow her calling.
- Practical advice for emerging artists on process, discipline, and understanding the business side of art.
Topics covered
- UnCovered: Madonna & Cher – concept, arrangements, and cast
- Reimagining pop through a soulful, theatrical lens
- The 2005 neo-soul moment and Divine Brown’s creative process
- Studio stories with Socrates, James Bryan, and Noah “40” Shebib
- D’Angelo, Brown Sugar, and the emotional power of soul music
- Storytelling across music, theatre, and film
- The evolution of pop music from the 1980s to now
- Billie, Sarah & Ella: Revolutionary Women in Jazz at Soulpepper
- Toronto’s creative community, mentorship, and Black Canadian artistry
- Growing up in a Jamaican household and choosing a creative life
- Deep-diving into the process and learning the business of creativity
Selected timestamped quotes
On reimagining Madonna & Cher at UnCovered
[00:02:16]: “They both have such really cool stories… Cher starting with Sonny and Cher, then branching out on her own, with music and acting. She’s picked some really great, memorable films, and she’s such a great interpreter of music.”
[00:03:13]: “Kevin and I sat down and talked about the songs. He’d say, ‘This is kind of the outline, do you have any input?’ I really loved that. It gives each song a unique flair and it really feels like a team effort.”
On the 2005 Divine Brown album era
[00:05:53]: “There was chaos around me… new management, my first record with a whole team of people. There were chaotic moments but beautiful moments. I really got to work with some great songwriters and producers.”
[00:07:15]: “I’d grab 40 before 40 became 40… he was just a young engineer intern at the studio. I said, ‘Come on, let’s co-produce something together,’ and that’s how we came up with ‘Twist My Hair.’”
On D’Angelo and Brown Sugar
[00:10:14]: “I remember when I heard the Brown Sugar album… from start to finish, I didn’t want anybody to interrupt me. It was creative genius, so raw, the perfect combination of funky, soulful, and sensual.”
[00:12:28]: “He was one of the biggest reasons I felt it was important to put out my own expression of soul music… to put out what my soul was speaking to me at that time.”
On storytelling across music, theatre, and film
[00:13:50]: “Storytelling has always been a part of who I am. There’s no separation for me between the different forms—on stage, on screen, in music. Any opportunity to be involved in storytelling, I wanted to be there.”
[00:16:06]: “With things like UnCovered and other theatres putting forth works that combine storytelling and concert, I get the best of all the worlds of expression that I really enjoy.”
On the evolution of pop and the magic of the 1980s
[00:17:39]: “We were talking about how special the music from the 80s was… you had this amazing cross section of music. When you look at the number one hits from 1985, it’s wild.”
[00:19:13]: “Pop music now has become a really homogenized sound. If something sticks out from what’s generally on pop radio, it’s an anomaly for a moment and then it’s gone.”
On Billie, Sarah & Ella: Revolutionary Women in Jazz
[00:24:33]: “Billie, Sarah & Ella was born out of a residency at Soulpepper… I wanted to create concerts that could tell a good story and highlight these women in a real, meaningful way.”
[00:25:28]: “Hearing Billie Holiday for the first time, I remember the pain in her voice and being fascinated by her unbelievably unique style. Then Sarah Vaughan sent me on a whole trajectory of research and inspiration.”
On Toronto’s creative ecosystem and mentorship
[00:30:38]: “Toronto is a tour de force when it comes to talent. Jackie was a mentor early on—she came to my house and talked to my dad so I could do Rainbow World. I love her for that.”
[00:32:29]: “I’m proud to be from Toronto, proud to be Canadian, and proud of my Jamaican roots. I’m part of a group of fantastically talented individuals I’ve worked with—from Kardinal to Glenn Lewis, Deborah Cox, 40, Drake, Melanie Fiona.”
On family, risk, and choosing art
[00:34:43]: “I got some licks for getting home late from gospel choir practice… but I wasn’t causing trouble. I just wanted to sing. I left home just as I was turning 17 so I could have the freedom to perform.”
[00:36:20]: “It was a tough go for sure, but I don’t regret any of it. I went to an alternative school to give me the freedom to be creative. I knew I had to do this.”
On advice for young creatives and the business of art
[00:40:13]: “I love watching younger people really dive into how creative they can be. There are so many times on stage where you have to improvise and figure it out on the spot.”
[00:41:07]: “Don’t be afraid to deep dive into whatever your creative process is. That’s how you learn. Everyone’s process is slightly different, but that’s the journey.”
[00:43:49]: “I wouldn’t call myself business savvy, but I learn as I go. People around me taught me how important it is to write your own material, because even in this digital age that’s still where a lot of the value is.”
About Divine Brown
Divine Brown is a Juno Award–winning Canadian R&B and soul artist known for her powerful five-octave vocal range, rich storytelling, and magnetic stage presence. Her self-titled debut album (2005) went Gold and produced the beloved classic “Old Skool Love,” while her sophomore album The Love Chronicles won the 2009 Juno Award for R&B/Soul Recording of the Year.
On stage, Divine has become a vital voice in Canadian theatre, performing in productions such as Father Comes Home From the Wars, A Streetcar Named Desire, Passing Strange, and her own acclaimed docu-concert Billie, Sarah & Ella: Revolutionary Women in Jazz at Soulpepper. She recently portrayed Hélène in the Canadian premiere of Natasha, Pierre & The Great Comet of 1812.
Her film and television credits include Schitt’s Creek, American Gods, BAXTER, Undercover Brother, and Amelia. Born and raised in Toronto to Jamaican parents, Divine continues to champion Black excellence, soulful storytelling, and creative risk-taking on stages across Canada and beyond.
Where to find Divine Brown
- Official site: https://www.divinebrown.com
- Instagram: https://www.instagram.com/db432hz/
- IMDb: https://www.imdb.com/name/nm1184827/
