The best advice Roy Woods ever received came from Drake. The then-recent OVO Sound signee and his label boss were walking down a hallway while on tour together in 2016 when The Boy decided to drop some wisdom. “He was about to go on stage, and he told me, ‘Just stay being you. It’s the best thing you can do,’” recalls Woods. “It’s very simple advice but it meant so much to me, to the point where now I thrive on being me and I can’t help it.”

To that end, Woods was unabashedly himself over the weekend when he opened up Roy’s Rum Shop with Havana Club, a one-time-only pop-up event that he insisted on doing his own way. For 48 hours, the artist transformed Toronto’s Mahjong Bar into a Caribbean bodega selling limited-edition bottles of Havana Club 7, designed by himself. Upon entering, a steady stream of devotees found themselves in a tiny front room where they could purchase the rum, beef patties, and exclusive merch. But walk past the cash register through a keyhole doorway, and Roy was there himself, rocking a golden owl chain and reclining Tony Montana-style behind a desk covered in dollar bills, waiting to hand you the bottle himself. Your typical brand activation this was not—the “Jealousy” singer took the time to chop it up with each and every listener, giving them a chance to get to know him. That’s just who he is.

And for those who already know him, Woods capped the weekend off with an invite-only party during which he previewed tracks from his highly anticipated, and highly personal, forthcoming album.

Havana Club Roy Woods meet and greet
Image via Havana Club

Not one for empty partnerships, Woods says his decision to link up with Havana Club was unforced; he’s been a fan of the rum for a minute, often sipping it for inspiration during studio sessions. “I consumed it regularly and was already familiar with the company and product, so I was like, OK, this is dope! You wanna work? Let’s get it!” Beyond that, the Caribbean connection—Roy’s family is Guyanese, Havana Club originated in Cuba—made it a natural fit.

“Who do I want to be? I’m still so young. I’m 25 right now. So I’m in that process of just trying to become more than I am, more than yesterday, better than yesterday.”

Woods’ heritage has had an indelible influence on him; you can hear tinges of it in his shadowy, confessional brand of alternative R&B. A native of Brampton, a suburb of Toronto with a robust immigrant population, he fondly recalls the bashment parties of his formative years. “Oh man, dancehall music and going to basement jams—growing up, that was the norm,” he says. “Nowadays, people go to the club, you just stand up and look cool. That’s not how I grew up partying. I remember going to basement jams and it’s lit! It’s an actual party. You got girls bubbling up everywhere! [Laughs.] I miss those days.”

Nostalgia happens to factor heavily into the Havana Club 7 bottle Woods designed. The label’s gnarled tree and full moon, as well as its blue and gold colourway, are nods to his brooding 2015 debut EP, Exis. Woods says his intention was to present fans with something familiar. “We wanted to give them a classic Roy vibe. When fans see it, they already know what it is.”

Roy Woods Havana Club bottle
Image via Havana Club

In some ways, this echoes the approach he’s taken on his as-yet-untitled second album. “I took a lot of flavours that people liked from the old me, and I try to mix it with what I’m doing right now, because I’ve been working a lot on my songwriting,” he says. “I’m trying to write songs for so many different situations, genres, and crowds, and really just open my mind and my talents to more. I believe it’s the best music that I’ve made so far in my life, so I can’t wait to show it to the world.”

“So far, it’s my most personal album. I don’t think anybody’s heard me say things that I’m going to say on this album yet.”

The project is the culmination of four years of serious soul-searching. A series of unforeseen circumstances, the pandemic being but one, left the singer in a dark cloud that found him reassessing his identity. He shares glimpses of that struggle on his vulnerable 2020 EP Dem Times. Sure, Drake had encouraged him to be himself, but Woods—who was signed by OVO at just 19, something he describes as an “out-of-body experience”—realized he still had to work on figuring out who that self truly was.

“It was just a lot of life, man. Just a lot of things I was not ready for—unexpected situations, losing a lot of close people in my life, and just trying to understand who I want to be as a young man and how I want to portray myself,” he reveals. “Who do I want to be? I’m still so young. I’m 25 right now. So I’m in that process of just trying to become more than I am, more than yesterday, better than yesterday. There’s been a lot of making mistakes, growing from them, and reflection.”

Roy Woods performing at the Havana Club bottle launch
Image via Havana Club

You can hear that process of self-discovery all over Woods’ new record, which he gave his inner circle a taste of at Saturday night’s Havana Club VIP party in Toronto. Esteemed guests—including OVO labelmate Baka, OVO Mark, producer DJ Charlie B, rapper Swagger Rite, and some of Roy’s oldest friends—were invited beyond Mahjong Bar’s variety store into the spot’s neon-lit backroom, where they enjoyed some rum cocktails and immaculate dancehall vibes harkening back to the singer’s Brampton days. They were also the first to hear the tunes Roy’s been cooking, as he hopped on stage to croon the unreleased material. There were some impassioned R&B anthems, some Caribbean-flavoured riddims (including a song he co-produced), and some of the most vulnerable lyrics the artist has ever penned.

“I talk about me, where I really came from, and just my story—the questions that people don’t really ask, you’re going to hear the answers to on the album,” says Woods of the new LP. The tracks see him open up about past relationships, friends who’ve passed away, and his come up. “It’s a whole bunch of emotions just all over the place. [Laughs.] So far, it’s my most personal album. I don’t think anybody’s heard me say things that I’m going to say on this album yet.”

Turns out getting all that off his chest was a healthy endeavour. Today, Woods is in a much “brighter place” than he was before, and feels like he’s at his most self-actualized. Knowing yourself, a wise man once said, is the beginning of all wisdom. And while the singer admits it’s still a work in progress, he’s now got a better idea of the man he aspires to be every day. All it took, really, was reconnecting with the old Roy, and the day ones who’ve been there to remind him who he’s been all along.

“I’m a small town kid from Brampton, you feel me? And then going from that to performing in arenas like Madison Square Garden, it was a lot,” says Woods. “Sometimes this gets crazy and you need somebody that you can lean on, that’s going to give you the real real—that raw raw. The people who know you, respect you, and love you ain’t there for your pocket; they look out for your well-being. Those are the people you need to keep around because they’re not going to give it to you any other way but the way you need to hear it.”