Dylan Sinclair has been building this story in public for a while. He first emerged as a teenager with Red Like Crimson in 2018, and every release since has pushed things forward without breaking the thread. Proverb in 2020 brought his first JUNO nomination, No Longer in the Suburbs in 2022 landed on the Polaris longlist, and FOR THE BOY IN ME in 2024 marked another step forward, both in how the music sounds and in how clearly he seems to know himself.
What makes his run interesting is that it has never really depended on one big spike. The growth has been steady, the audience has stayed, and the work has kept sharpening. By 2025, that started showing up on a bigger scale too, from Black Music Month work with Amazon Music and Leon Thomas to a sold-out hometown show at The Danforth Music Hall and an international run across Europe.
Coming out of Toronto, he knows exactly what kind of R&B lineage he is part of. But the way he talks about his own path is less about hype and more about staying rooted, getting better, and letting the music grow with him.
You’ve grown up in Toronto, which has such a strong identity when it comes to R&B. Where do you feel like you sit in that space right now, and what do you want to do differently?
From PARTYNEXTDOOR to Daniel Caesar, Drake and The Weeknd, I’m proud of my city and everything it has to offer when it comes to R&B. Those are genuinely some of my favourite artists, period. When it comes to where I fit in, I definitely feel respected as the next one to do it. People always tell me they see a bright future for me and that definitely keeps me going, knowing that they wanna see me win.
There’s a real sense of honesty and warmth in your music. At a time when everything moves so fast, what makes you hold on to that?
Not sure. I was just raised in a genuinely loving environment where I was encouraged to be open and honest. I think that’s shaped the type of person I naturally am today.
Your newer work feels clearer and more self-assured. What changed for you between your earlier and latest records?
I’m older now. I’m more mature. More responsible and accountable. The music’s gonna reflect that.
A lot of artists today break through one big moment online, but your journey has been steadier. What has that kind of growth shown you about the people listening to your music?
Yeah, I’m very grateful for every last one of my listeners. They’re loyal and they have great taste if I do say so myself. I’m cool with being the “if you know you know” guy. That viral moment will come and it’ll hit way more because I’ve been growing a solid foundation for a minute now.
When you’re writing now, do you usually know exactly what you’re trying to say, or are you figuring it out as you go?
I used to write out all my lyrics before getting in front of the mic. Now, I produce all my demos, so while I’m finding chords and cooking up a beat, I’ll wait for that moment to catch where I find a concept that fits the feel of the music, and once I find that, I run with it.
I punch melodies in and figure out lyrics as I go, but I usually record it all myself cause it all happens very quickly. It’s thoughtless.
When you think about what’s next, what does that actually look like for you—and what would make it feel like you’ve really made it?
Bigger stages, stronger sets and expanding my sound while remaining rooted in what’s gotten me here. Especially now that I have my U.S. visa, touring is all I can think about. I’ll know I’ve made it when I don’t have to question if this is sustainable anymore.. when music fully supports my life and I’m moving with intention rather than survival.
What can you tell us about your upcoming releases?
I produced all the demos, so the music’s very me. No half songs.
What do you think about the Future of Music in Canada?
Man…Canada’s always produced the best artists and that’ll never change.
Holzman and Hughes at the Lincoln Memorial Reflecting Pool.Courtesy of Ekko Astral
Holzman and Hughes in Brooklyn, May 2026.Griffin Lotz for Rolling Stone
There’s no immediate resolution in any of this. There’s no surrender either — and a lot of great escape. White’s slide guitar in “Dollar Bill” sounds like a National Steel on steroids until the solo, when it turns into what seems like a theremin gone postal. “I Can’t Believe What I’m Hearing” has a great pop-wise chorus closer to the Pretty Things than Son House. And don’t miss White’s wry aside to the White Stripes’ old creation myth in the second verse of “G.O.D.,” on the way to the real business at hand. “Well, it’s the beginning of the world now,” he declares at the song’s end. “Let’s do it all over again.”
Jay-Z has turned the 30th anniversary of his classic debut album into a major marketing event
Jay-Z Knows the Past Still Pays
There’s a pleasant absurdity to the advertisements for JAŸ-Z30 that are currently found across New York’s subway tunnels. Their dramatic imagery — a stark black backdrop pierced through the center with a pair of hands, presumably Jay’s, fixed into the famous Roc diamond — invites a kind of religious authority that feels a touch ironic for anyone who’s old enough to remember all types of handwringing over those very hand symbols only a few years ago. And maybe that’s the point. By now, nostalgia’s grip extends layers deep. So much so that you could find yourself waiting for the train, reminiscing on the days when people still made jokes about the so-called Illuminati.
Jay-Z’s months-long campaign commemorating the 30th anniversary of Reasonable Doubt and the 25th anniversary of The Blueprint has indeed resurfaced the rapper-turned-mogul’s success story. Reasonable Doubt, released in 1996, positioned Jay as not only a resonant voice in hip-hop but also in the increasingly lucrative business around it. After major labels passed, the album was released independently through Roc-A-Fella Records and Priority Records, setting the tone for Jay’s career as a business…man.
And in the full-court press campaign around this summer’s anniversaries, culminating in this weekend’s trio of performances at Yankee Stadium, Jay’s business acumen is again at center focus. You’d be forgiven for throwing around buzzwords like “multichannel” or “cross-platform” to describe the slate of festivities. There was a Spotify-backed takeover of the J and Z trains; custom JAŸ-Z30 subway maps and a Google Maps guide; commemorative Brooklyn Public Library cards; and most recently Bowery Station and DUMBO pop-ups with archival footage and merch. (That these Yankee Stadium shows come on the heels of Taylor Swift’s wedding at MSG suggests some sort of mega-rich takeover of cultural institutions, but let’s leave that one for another day.)
The moves come as nostalgia continues to drive a considerable chunk of the music industry’s profits. In an era when old songs can circulate infinitely on streaming platforms, gaining new life in the form of everything from samples to memes, and when superfans are willing to spend on physical goods, limited merch, and live experiences, album anniversaries have become their own product launches. Jay-Z’s Reasonable Doubt campaign is only the splashiest recent example.
No wonder, then, that Beyoncé already appears to be setting the stage for her own run of commemorations for the upcoming 20th anniversary of her album B’Day in September. Over the weekend, she released her first new song in two years, titled “Morning Dew (Donk),” to tease the upcoming reissue. According to Luminate, older music still dominates attention, with only 43 percent of U.S. on-demand audio streams in 2025 coming from tracks released in the previous five years. This is also one reason why vinyl and physical formats have seen renewed value in recent years, with the RIAA reporting that vinyl sold 46.8 million units in the U.S. in 2025, compared with 29.5 million CDs. Luminate says superfans are 20 percent of U.S. music listeners and spend heavily on live events and physical merchandise; 73 percent of these fans purchase physical merch, versus 26 percent of general music listeners.
In today’s industry, having a major anniversary is like having a new product to promote, a way to participate in an already thriving marketplace for nostalgia. The demand is visible well beyond official artist stores: Vintage concert tees now trade as collectibles, with one 1967 Grateful Dead shirt selling at Sotheby’s for $19,300 and rare rap tees treated as wearable archives of hip-hop history. Anniversary campaigns give artists and labels a way to reclaim that energy, turning the secondary market’s appetite for old symbols into new, officially sanctioned products.
Jay-Z’s official anniversary store turns that logic into a menu of objects: a $1,500 collector’s crate, a $300 cassette box, $400 Yankees jerseys, and four-figure varsity jackets. Of course, Jay is far from alone when it comes to legacy acts cashing in on nostalgia. He’s more like one salient example of a much larger wave of artists and promoters marketing anniversary products that includes the Smashing Pumpkins’ Mellon Collie and the Infinite Sadness 30th anniversary super-deluxe edition, My Chemical Romance’s Black Parade stadium tour, and the returned Warped Tour, among many others.
Five years before Reasonable Doubt became the occasion for library cards, pop-ups, collector crates, and stadium spectacle, its 25th anniversary was marked by an NFT. In 2021, Sotheby’s and Roc Nation auctioned a one-of-one Derrick Adams artwork tied to the album, billed as the only official Jay-Z-authorized commemoration of the anniversary. Around the same time, Roc-A-Fella was in court over co-founder Damon Dash’s attempted sale of a Reasonable Doubt-related NFT, a dispute that ended with a judgment making clear that no shareholder could sell or dispose of an interest in the album — including through an NFT — without the company’s authorization.
That ownership question is becoming harder to avoid as music enters the AI era, where the archive is not only something to reissue, exhibit, or sell, but something that can be scraped, modeled, and trained on. Last week, SZA took to Twitter to express frustration with AI music company Suno, notably calling out Diplo by name as one of the company’s investors. “DO NOT GIVE AWAY YOUR VIBRANIUM !!! DO NOT TRAIN AI WITH YOUR GENIUS,” she wrote on Twitter. Her complaint was joined by Kenneth Blume, who said Suno’s workers were “stealing from countless struggling musicians.”
For an artist with a legacy as impactful as Jay-Z’s, the current anniversary boom feel like the latest phase of a longer project of deciding who gets to turn hip-hop history into intellectual property. Jay-Z’s legacy deserves preservation; few catalogs have made a stronger case for it. But the more that preservation arrives through limited-edition objects, auction platforms, luxury merch, and authorized experiences, the more it has to answer a harder question: When does protecting the archive become another way of extracting value from it?