Jeremy Haywood-Smith is a Winnipeg-born, Montréal-based, singer/songwriter, musician and creative mastermind behind the acclaimed, boundary pushing project JayWood. Though he was nominated for a Polaris Music Prize, the Canadian artist currently has a day job as a postal worker, which is arguably the least interesting thing about him.

Haywood-Smith’s third JayWood album Leo Negro is slated for a September 5, 2025 release through Captured Tracks. Much like previously released tracks “UNTITLED (Swirl)” and his collaboration with Tune-Yards, “BIG TINGS,” Leo Negro will further cement his reputation for refusing to be easily pigeonholed.

The Canadian artist explains that the album’s title ” . . .came from the main concept of the album which is identity. I asked myself the question of ‘What are some things that make me who I am, no matter what changes occur in life?’ and funnily enough, I was getting really into astrology at the time due to fact that 70% of my friends are queer femmes. I was trying to understand what it means to be a Leo. On the other hand, I’m moving through life as a black man in spaces that don’t always understand me or will try to categorize me.”

He adds, “I know the main identifier for Leos is that they’re super confident and massive social magnets and leaders, but in recent years, I’ve had a harder time leaning into that specific energy, so I started to just dismantle the idea of confidence and leadership by doing somewhat of the opposite. I started to get more vulnerable and share more things about myself: insecurities, fears, anxieties, my scarier truths and my experiences as a black person. Through that, I weirdly started to feel a little more confident. Which brings me to my last point about the title. I now live in Montreal and one thing I realized while trying to learn the language is that the descriptions of things are at the end. For example ‘black cat’ would be ‘chat noir,’ and if I look at my album title, it kinda translates to ‘black confidence’ in my mind.”

Leo Negro‘s latest single “ASSUMPTIONS” is a mind-melting, defiantly genre-agnostic track that sees the Montréal-based artist meshing a swaggering and braggadocio-fueled hip-hop production and neo-soul while subtly hinting at Pharrell‘s “Happy.” While seemingly recalling Tyler, the Creator, Stereolab and Men I Trust among others, “ASSUMPTIONS” showcases a mischievously forward-thinking producer and songwriter, who can pair social commentary and deep introspection within a catchy, deceptively fun bop.

“‘ASSUMPTIONS’ feels like it’s giving myself permission to step into some new sonic territory,” Haywood-Smith explains. “It’s fun and playful while still being pretty focused and lyrically consistent, which is new for me. It’s also one of the funniest songs I’ve ever written. It’s literally about my crippling imposter syndrome but at the same time, I’m staking my claim as a solid artist and a producer.”

Directed by Trent Wayne, the accompanying video is a playful, unpredictable mix of cartoons and live action footage at an equally cartoon colored party, in which he plays his new song. Much like the accompanying song, the video touches on feelings of imposter syndrome, feeling under appreciated yet knowing deep down that you’re fucking dope.

The video’s director, Trent Wayne, while speaking on the production said “JayWood set the tone for us—playful, unpredictable, and musically rich— making a great foundation for the video. Inspired by the song’s genre-blending, we built a narrative to match: starting in a comically chaotic party scene, drifting into a Yo Gabba Gabba!-inspired graveyard, and featuring a cartoon version of Jay performing created by Pete Though, which was sent through a VCR for added analog grit. Our production designer, Sophia Kotowski, built a functional CD-player gravestone that became a psychedelic centerpiece. Collaborating with Captured Tracks to spotlight innovative artists like JayWood is a real privilege for our team.”