Dylan Sinclair, a Toronto R&B King in the Making

The emerging singer on his new EP 'No Longer in the Suburbs,' the influence of Filipino karaoke, and a long-lost album by his and Daniel Caesar's dads.

Close-up of Toronto R&B star Dylan Sinclair's face
Complex Original

Image via Complex Original/Sid Naidu

Close-up of Toronto R&B star Dylan Sinclair's face

Dylan Sinclair has been thinking a lot about his surroundings lately.

“Environment is a big thing for me,” the 20-year-old R&B singer tells me, sitting in a bright room in Toronto’s Harbord Village area. “A sunny day like this, the outcome of a song would be totally different than on a rainy day.”

It’s not just weather, but location that informs Sinclair’s creative process. Which makes sense. Where you are influences what you do and how you feel. Anyone who’s taken a psychogeography course can tell you that. Light affects our circadian rhythms; landscapes affect our emotions. A long walk can miraculously uplift your mood; a leisurely bus ride can spawn the song of the summer.

It’s why, about a year and a half ago, Sinclair moved out of his parents’ house. After breaking out with his self-released, deeply personal album Proverb in 2020, he suddenly found himself with a Juno nod for Traditional R&B/Soul Recording of the Year, millions of streams to his name, and scalding-hot buzz as Toronto’s next R&B sensation. Most kids living at home are content just making the honour roll. He admits he was worried about not having enough experiences to draw on for the follow-up project. “All that really told me is, ‘OK then why don’t you just go and live some more life?’” Sinclair explains. “I always say, you can’t tell the story until you live it. I had to no longer be in the suburbs. I had to make adjustments to my life that would allow me to experience new things.”

Dylan Sinclair poses against Toronto skyline

So, like any good hero’s journey, Sinclair departed from the world he knew. He left the comforts of his Filipino-Guyanese family’s home in Thornhill, Ontario and set forth for Toronto. It wouldn’t take him long to find some fresh source material. His new EP, aptly titled No Longer in the Suburbs, details all the freedoms, temptations, and torments that come with being on the cusp of fame in a city full of distractions. “It’s about finding that extra stimulation and figuring out what it means to find myself,” he says.

Spanning eight confessional, meditative R&B tracks, the new EP is a sonic bildungsroman, hearing Sinclair work through the moral trials he faces as he enters manhood and gains prominence. At its heart is a tension between the familiar and the foreign. On slow-melting lead single “Suppress,” he grapples with his desire to stay in a committed relationship while ascending to stardom, lamenting about “wanting to be a much better boyfriend” in the velvety, internal temperature-raising voice that’s gotten him this far.

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“A lot of the songs are about my girlfriend, who, a couple months into me moving into the city, we got together,” he says. “I’m just trying to navigate that, especially while I’m gaining a little bit of attention with my music. Is this what I want? You don’t see it too often. People advise against what I’m doing when I say that [I’m] in a relationship. I’m trying to remain at peace with myself, but also achieve the goals I want to achieve and still have this person in my life… I still have my values amidst all of the things that are going on around me.”

"There’s Danny [Caesar] and me, but there’s also Norwill Simmonds and Kevin Sinclair. They’re, like, very good singers. That’s where all of our vocal skill comes from."

No Longer in the Suburbs is about Sinclair’s fight to remain grounded while everything in his orbit changes. One way he stays level-headed is by keeping his Day 1s close. His roommate in Toronto is his good friend and working partner Zach Simmonds (and his dog Kippa), who co-produced half the tracks on the new EP and sang backups on “Too Soon?” Fun fact: Zach also happens to be Canadian R&B star Daniel Caesar’s younger brother. Notable, considering Sinclair often gets compared to Caesar.

Even funner fact: “Our dads have an album together,” Sinclair chuckles. He’s not kidding. “There’s Danny and me, but there’s also Norwill Simmonds and Kevin Sinclair. They’re, like, very good singers. That’s where all of our vocal skill comes from, I would say.”

Dylan Sinclair and Zachary Simmonds and their dog

The Sinclair and Simmonds families grew tight years ago as members of the Seventh-Day Adventist Church. At masses, Dylan’s father Kevin and Daniel and Zach’s father Norwill would often bring the house down with their arresting vocals. Around 2001, they recorded and released a collaborative gospel album. Good luck finding this hidden CanCon gem on streaming services. “I don’t even remember the name of it. That needs a proper release, like actually,” Sinclair says of the project, which dropped the year he and Zach were born. “Those are the real Gs right there. I love when we get together for barbecues sometimes at Danny’s place, with all of the family together. It’s so cool seeing our dads interact, knowing what we’re trying to do now. That’s where we got that gospel influence for sure.”

Dylan is, in many ways, a product of his environment. Like Caesar, he honed his voice over many years of singing with his family at church, joining the choir at just four years old. Besides his dad, who’s Guyanese, being an obvious influence, he credits his Filipino grandpa, from his mom’s side, for encouraging his development. “My lolo played a lot of guitar and piano every Saturday morning. [One day] he was practicing for church and I was just singing along with him. He was like, ‘Yo, I think you should come on stage and duet with me.’” The eventual performance marked his first taste of the spotlight.

Dylan Sinclair poses against mural

Music was always a family affair for Dylan. A communal experience coming from a pure place. Like most Filipino households, the Sinclairs got a ton of mileage out of their karaoke machine. “We did a lot of karaoke growing up, actually,” he laughs. “I ended up liking a lot of very sing-along songs. Because Filipinos love to sing, a lot of the music that was played growing up were songs you can sing along to.” It’s had a lasting effect. “Even when I approach my music now, I try to write melodies you can sing back. I want the live show to be like a big karaoke session. [Laughs.]”


"I want to make classics, not just hits."

You can hear this on his 2018 debut EP Red Like Crimson, a pacifying collection of gospel-inspired R&B jams. His voice sounds seasoned and soulful, his melodies reminiscent of a time when men pleaded with their lovers by belting ballads in the rain. Sinclair admits his style early on was inspired by Caesar, who in an era of Toronto music dominated by nocturnal, Auto-Tuned R&B, showed him it was possible to find success singing stripped-back songs brimming with love and light. After being tipped to Dylan’s work by Zach, even Caesar himself was impressed with what he heard. He showed the songs to his Golden Child Records producers Jordan Evans and Matthew Burnett, who quickly became fans. The three of them would attend a “little showcase” Sinclair held for his EP—along with over 200 other people, all led there through word of mouth and social media posts.

Dylan Sinclair with his dog

The hype surrounding the event caught the attention of Jordon Manswell, who’s produced for Caesar, as well as Chris Brown and Mariah Carey. He messaged Sinclair directly, offering to work with him. “The chemistry was like [snaps fingers] instant. It just worked right away,” recalls Sinclair. “It was a couple of songs and then we had ‘Home’”—his breakthrough single. Manswell would go on to executive produce Proverb.

Sinclair’s Juno-nominated album had clear gospel influences and nods to Caesar and Frank Ocean. No Longer in the Suburbs, though,is the sound of the young artist venturing not just out of his cul-de-sac, but off the map. The inspirations here are harder to pinpoint, the atmospheres more unearthly, as Sinclair finds a voice that’s singularly his own. “Open,” produced by Manswell, has him gliding over a playful, shuffling beat and plunking guitar line as he tries to convince his girl he’s not the player type. But on “Lifetime,” anchored by stirring strings and acoustic guitar, he sounds less certain: “I hope I don’t change with the wind,” he sings in a whispered falsetto.

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How sure is anyone of themself at 20, really? Sinclair admits he’s still “figuring things out” as he enters adulthood, but he’s spent a lot of time thinking about the type of man he wants to be. He’s got a value system, and like an R&B Luke Skywalker, he’s determined to not let outside forces sway him. While Caesar wound up leaving the church in his youth, Sinclair’s faith hasn’t wavered. “I definitely have a lock with God that will probably never go away,” he says. “As I grow up, put myself out there, and embrace new experiences, I feel very grounded when I talk to God in the morning.”

On Suburbs, Sinclair displays a knack for compellingly candid storytelling reminiscent of a young Usher (whose Confessions he credits as an influence). Only, unlike Mr. Raymond—and many of his Toronto R&B cohorts—he’s resolutely an anti-lothario, doing his best to resist the Dark Side. “If there’s a version of yourself that you really love, you have to figure out, why do I like this person so much?And prioritize it. It has to do with the people around you. It has to do with the space that you’re in,” he says. “I move with the same people. I feel that’s necessary in order to really take your music to a certain level, cause that’s what a lot of the biggest superstars we have now do. At least the ones in our city—XO, OVO, they have their core friend group and they just grow up with them.”

Snaposhots of Dylan Sinclair's day in Kensington Market

Sinclair knows that to make it in this industry, he’ll need to wander far away from home. But with the right crew around him—his homies, friends from church, his girl—he can feel at home anywhere in the world. Music is still a family thing to him. Sure, time will tell if he can keep that family together—but in the interim, hearing him sing honestly about trying to make it work is nothing short of transfixing. Isn’t that the stuff R&B legends are made of, after all?

He’s thought about that too, by the way. “I’ve been thinking about my legacy since I was like 15,” Sinclair laughs. “It’s matured over the years. I want to make people’s days better with my music and do that for as long as I can. That’s not to say I need to be making albums until the day I die, but I want to make albums that last beyond that. I want to make classics, not just hits. I want to make music that feels better the next year, and just continues to grow on you. I want one of those. Or a couple of those, hopefully.”

In fact, Sinclair’s in the planning stages for one of those right now. He’s been pondering where to record his next album. Another move will likely be necessary. “I’m between Montreal, Hawaii, and Bali. All very different locations,” he snickers. “I just know I want water and a big window. A visual of unknown territory.”

Creative Director / Producer: Alex Narvaez
Photographer: Sid Naidu, Alex Narvaez
Photo Assistant: Millicent Amurao
Production Manager: Jessica Campbell
Production Coordinator: Kylie Laus
Artist Management: Jermayne Clayton, Jordan Manswell
Publicist: Michael Tomczak

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