The Multiple Layers of JayWood

The rising artist is giving himself permission to step into new sonic territory, crafting a concept album that captures the various dimensions of his personality.

By Adriel Smiley

Photos by Ryo Sato

Published on September 3, 2025

While most Montrealers are just starting their day, rising hip-hop personality Jeremy Haywood-Smith (otherwise known by his stage name JayWood) is already on the move. Connecting with RANGE from his car, bright and early, he’s headed to his job as a postal worker.

Originally from Winnipeg, JayWood’s recent move to Montreal marks the next step in his music-making journey. A new city comes with its own set of real-life challenges, and his latest album, Leo Negro, embraces the vulnerability of that transition in a way he hasn’t explored before.

The “Leo” in the album’s title is in an astrological sense. Much of JayWood’s early musical inspiration stems from his mother, who is also a Leo. One of the main identifiers for Leos is that they’re confident, charismatic, and natural-born leaders, descriptors that JayWood has found it challenging to embrace. This has come along with a new understanding of his relationship with attention.

“I realized that I have a love-hate relationship with the idea of getting a lot of attention,” he tells RANGE. “I’m from Winnipeg, and in my small, big city, when I was getting a lot of attention for music stuff, I was like, ‘I don’t know if I really like this.’ It was distorting my brain in a way. I’m feeling everyone’s projections.”

That discomfort gave him pause—especially when he considered what could happen if he leaned too hard into the spotlight.

“I saw that if I were to lean more into the Leo version of myself, and let that gas me up, I don’t know if I would be making the music I want to be making because I would just be thinking ‘Alright, I’ll kick my feet’ if I made it. Getting into that big-headed ideation too early is detrimental to being creative.”

This project is his attempt at a concept album—cohesive thoughts blended together. Many of his favourite artists, such as Outkast, Tyler, The Creator, and Frank Ocean, have built their careers on that kind of vision. His enthusiasm for this collection of songs is pure: a childlike sense of pride in his work.

“I’m a sucker for a concept album, a through line, intention, weaving together,” he says. “One thing I was so stoked about for my record is that I finally got, like, a seamless record, which I’ve been trying to do for such a long time.”

JayWood is an artist who’s difficult to classify, and the urge to fit into a category is something even he has struggled with. In a recent video he posted on Instagram, he talks about “finding his niche,” and in discussing that journey, he offers a lot of self-insight.

“I kind of keep going back and forth,” he says. “Maybe it’s not my job to actually find my niche. And maybe I present something and it forms an idea. I think I’m trying to be less targeted about finding a niche. And I think that maybe I had the wrong angle about that.”

It’s refreshing to hear an artist as versatile as this pull back some of the layers. In an era where mystique holds so much power, JayWood seems uninterested. The authenticity of his experience has more value here.

The track “Assumptions” stands out on Leo Negro. Among a group of interesting records, it feels like the most digestible for the casual listener, sure to attract new fans. More importantly, it’s the most hip-hop track of the bunch.There are reasons you can point to—hooks, structure—as to why it feels like a good entry point. But there’s also an intangible feeling that makes it stick.

“It’s funny, when I wrote it, I had a hook, I had a very prominent hook. This is catchy to me. Anyone I showed it to was like, ‘That’s the song.’”

Despite that, JayWood wasn’t instantly sold. He called it predictable—a structure that had been seen before, and one that worked. So, he tweaked it to make it more of a JayWood record, and had the foresight to know which songs were meant to be singles and which were not.

“Then I took some creative liberty and was like, ‘Man, let’s bring back bridges. Let’s bring back a fucking bridge.’ And I just threw a bridge in there that made me feel excited about the song again. And the outro is like, ‘Alright, let me just have fun with it,” he says. “But it felt like a single because it just did the things that I guess an audience would be able to get on board with. Whereas a song like ‘Ask for Help’ doesn’t even have a chorus.”

On “Gratitude,” he explores the idea of never being enough—a function of his relationship with ego. The song celebrates multiple sides of who he is, and he explains how that inner tension affects his music.

“I think ego is a big part of the record as well,” he says. “I imagine myself having two versions of myself, and there’s a power struggle within the record. Do I lead with ego or do I lead with vulnerability? How do we find a mix between the two? There’s a self-check-in that happens on the record. We tried the ego thing, we tried the boisterous version of yourself that’s not working, that’s not sustainable, and it’s not making you a better person, it’s not making you a better artist.”

JayWood’s music has always had a sense of playfulness, but Leo Negro introduces a different kind of depth. It’s stitched together with intention, and the confidence feels more grounded.

As he navigates the growing pains of a new city and a sharper understanding of self, JayWood is less interested than ever in fitting into a box. Leo Negro is not about finding a final answer—it’s about enjoying the process of growing and changing.