Uproxx Music 20: Dylan Sinclair’s ‘For The Boy In Me’ Champions The Beauty Behind Love And Intimacy

Dylan Sinclair 'Uproxx Music 20' interview
Mary Chen/Merle Cooper

At just 23 years old, Toronto singer Dylan Sinclair has plenty of experience in the music industry and the success to match it. His debut project Proverb, released in 2020, received a nomination for Traditional R&B/Soul Recording of the Year at the Juno Awards Of 2021. Two years later, his second project No Longer In The Suburbs was longlisted for the 2023 Polaris Music Prize. These two moments, along with others, helped to stamp Sinclair’s talents, which come alive more than ever on his official debut For The Boy In Me.

The 12-track project, complete without guest features, is an ode to being in love and in a stable relationship. “In a world where men are not encouraged to be vulnerable, this album For The Boy In Me disregards that, choosing to tell it like it is,” Sinclair said about the album in a press release. The feel-good spirit Sinclair exudes lives on records like “Lemon Trees,” a song made for driving with the windows down and soaking in a warm breeze. “Slo Mo” wades into intimate waters as Sinclair sings about passionate moments in the bedroom while “IMY” lands as a moving ballad about longing for a partner’s physical presence. Altogether, Sinclair uses For The Boy In Me to detail the beauty of the love and intimacy and the many ways it shows up in a solidified relationship.

Together with the release of For The Boy In Me, Uproxx spotlighted Sinclair for this week’s Uproxx Music 20 column. Scroll down to learn more about the Toronto native’s influences, inspirations, and aspirations.

See Previous UPROXX MUSIC 20 Interviews:

What is your earliest memory of music?

Worship music.

Who or what inspired you to take music seriously?

A lot of moments and a lot of people but primarily, Daniel Caesar.

Do you know how to play an instrument? If so, which one? If not, which instrument do you want to learn how to play?

I’m always down to learn new instruments cause I pick them up fairly quickly but I put most of my time into the piano.

What was your first job?

Customer service rep at an RESP call center called Heritage RESP.

What is your most prized possession?

Probably my Acura ILX because right now I live outside the city and I don’t like transit.

What is your biggest fear?

Being broke and lame.

Who is on your R&B/rap/afrobeats Mt. Rushmore?

Right now I’ll say Stevie Wonder, D’Angelo, Beyoncé & Alicia Keys, but that’s hard.

You get 24 hours to yourself to do anything you want, with unlimited resources: What are you doing? And spare no details!

Wake up. Have a smoothie. Work out. Eat some Filipino food for breakfast. Go to the beach with some friends. Get drunk. Have fresh fish tacos for lunch. Go home to shower. Go on a dinner date and see where the rest of my night leads.

What are your three most used emojis?

🥲, 🤌🏾, and ❤.

What’s a feature you need to secure before you die?

I love Laila!

If you could appear in a future season of a current TV show, which one would it be and why?

Noluvmar’s 20v1 series. Maybe I’ll find my wife there.

Which celebrity do you admire or respect for their personality and why?

Pharrell. His creativity is contagious and he’s always evolving.

Share your opinion on something no one could ever change your mind about.

Filipinos are the sweetest people in the world.

What is the best song you’ve ever heard in your life and what do you love about it?

Playboi Carti’s “Flex” featuring Leven Kali. It’s just one of those. If you know, you know.

What’s your favorite city in the world to perform, and what’s a city you’re excited to perform in for the first time?

I love London’s energy. I’m looking forward to performing in the Philippines and Australia.

You are throwing a music festival. Give us the dream lineup of 5 artists that will perform with you and the location where it would be held.

Ask me this in a few months. My favorite artists are my friends and they haven’t released music yet.

What would you be doing now if it weren’t for music?

I have no idea. Around the time that I was getting into music more consistently, I was also getting into skateboarding so maybe I would’ve stuck with that.

If you could see five years into the future or go five years into the past, which one would you pick and why?

The past of course. Then I can do what I’ve done but better because of what I know now. The future belongs as a mystery.

What’s one piece of advice you’d go back in time to give to your 18-year-old self?

Carve out your own lane.

It’s 2050. The world hasn’t ended, and people are still listening to your music. How would you like it to be remembered?

For it to be remembered in itself is lit enough to me. The “how” is up to the listeners.

For The Boy In Me is out now Five Stone Records Inc. Find out more information here.

TheBasement LA Returned With Baby Tate, Maeta, And More

TheBasement returned to LA on Wednesday (February 22) with a stacked lineup including a surprise appearance by Atlanta rap standout Baby Tate and the return of burgeoning R&B star Maeta, who last performed at TheBasement in 2018.

The live showcase has been a premiere destination for some of hip-hop and R&B’s breakout artists; in November, Brooklyn native Lola Brooke brought her viral hit “Don’t Play With It” to the West Coast ahead of her ongoing world takeover, while a prior show featured GoGo Morrow and KenTheMan, both breakout stars in their own rights.

Get to know the show’s most recent performers, including Dylan Sinclar, Lil Vada, and Shady Blu, below.

Some artists covered here are Warner Music artists. Uproxx is an independent subsidiary of Warner Music Group.

Baby Tate

Baby Tate has been an Uproxx cover artist and a fixture on soundtracks from some of your favorite shows including Insecure. She recently teamed up with Kenneth “Babyface” Edmonds on his 2022 album Girls’ Night Out, joining him on The Tonight Show to perform their collaboration, “Don’t Even Think About It.” Tate’s latest mixtape, Mani/Pedi, dropped in September featuring records like “Slut Him Out” and “Ain’t No Love.”

Dylan Sinclair

Canadian singer-songwriter Dylan Sinclair was nominated for a Juno Award for his debut album Proverb in 2021. He’s a soulful presence in the vein of countryman Daniel Caesar, with a smooth vocal delivery and emotive, plainspoken lyrics that clearly evoke the wealth of feelings that pervade modern relationships. His most recent EP, No Longer In The Suburbs, is out now. “I’ve just started performing live shows and I’m enjoying this stage in my career,” he says. “Hope you do too.”

Lil Vada

Pronounced “Vay-dah,” this LA native has a gift for producing some of his hometown’s finest ratchet anthems. He’s been picking up steam over the past month or so as his high-energy reimaginings of 2000s club favorites have gained traction in the streets. He’s got a deceptively straightforward delivery that slots easily into the well-worn swing pocket favored by LA’s current crop of post-gangsta rappers and a sense of playfulness about his menacing boasts. “I want people to understand that my energy is different and my passion for music comes from hunger and the need to make my dad proud,” he says.

Maeta

Returning to TheBasement for the first time since 2018, Maeta wants listeners “to feel unapologetic about their sexuality, mistakes, and feel comforted through the uncertainty of life and love.” Since her last appearance at TheBasement when she was 17 (her first performance ever), she says she’s a “whole new girl” — and her resume since then can back that up. In just the past month, she’s appeared on Vic Mensa’s new single “Strawberry Louis Vuitton” after collaborating with the likes of Ambré, Beam, Buddy, Kaytranada, and more.

Shady Blu

Shady Blu is a walking testament to the power of shooting your shot. A cold email to famed TDE engineer MixedByAli led to a deal with his label getting advice from LA’s rap uncle Snoop Dogg, and a steadily rising presence in the rap game. Her unconventional style will certainly be a draw for fans of TDE’s woozy backpack rap influenced style but she’s also doing her own thing. She wants listeners “to really give the music a chance and listen openly” because “I may say something you feel too.”

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Via Dennis Larance
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Via Dennis Larance
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Via Dennis Larance
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Via Dennis Larance
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Dennis Larance

The Best Canadian Albums of 2022

Image via Complex Original/Samuel Iannicelli
  • Image via Publicist

    20. Dylan Sinclair, ‘No Longer In The Suburbs’

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    19. Chung, ‘See You When I C U’

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    18. Raccoon, ‘C00N: la prophétie’

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    17. Thelonious, ‘Albion Road Demos.’

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    16. Pierre Kwenders, ‘José Louis and The Paradox of Love’

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    15. Mike Shabb, ‘Sewaside II’

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    14. Nate Husser, ‘All Time High’

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    13. DJ Charlie B, ‘Across the Board’

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    12. Dvsn, ‘Working On My Karma’

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    11. Tanika Charles, ‘Papillon de Nuit: The Night Butterfly’

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    10. Savannah Ré, ‘No Weapons’

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    9. Nav, ‘Demons Protected By Angels’

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    8. Snotty Nose Rez Kids, ‘I’m Good, HBU?’

  • via OVO

    7. Drake & 21 Savage, ‘Her Loss’

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    6. Adria Kain, ‘When Flowers Bloom’

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    5. Nicholas Craven & Boldy James, ‘Fair Exchange No Robbery’

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    4. Backxwash, ‘His Happiness Shall Come First Even Though We Are Suffering’

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    3. Jessie Reyez, ‘Yessie’

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    2. Drake, ‘Honestly, Nevermind’

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    1. The Weeknd, ‘Dawn FM’

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

Image via Complex Original/Sid Naidu
Image via Complex Original/Sid Naidu

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 making your own way while being on the cusp of fame and fortune. “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.

“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, 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.”

Image via Complex Original/Sid Naidu

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. “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.

Image via Complex Original/Sid Naidu

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.

Image via Complex Original/Sid Naidu

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.

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, 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.”

Image via Complex Original/Sid Naidu

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

Best New Canadian Songs: The Weeknd, Daniel Caesar, Houdini

Image via Complex Original/Alex Milani

  • YSN Fab, “Wanna Know”


  • Dylan Sinclair, “Lifetime”


  • Sidhu Moose Wala f/ AR Paisley, “Love Sick”


  • Justin Bieber f/ Don Toliver, “Honest”


  • The Weeknd f/ Kaytranada, “Out of Time (Remix)”


  • Houdini and NorthSideBenji, “Repeat”


  • Daniel Caesar f/ BADBADNOTGOOD, “Please Do Not Lean”


  • Magi Merlin, “Pissed Black Girl”


  • Sarahmée f/ FouKi, “Quand la route est longue”


  • Aquakultre, “Don’t Trip”


  • Ardn, “Jupiter & Mars”


  • Portion, “Eastside”