JayWood lay the groundwork for his upcoming EP in 2015, when the idea of recording for an influential New York label seemed like a pipe dream

Jeremy Haywood-Smith’s newest songs are actually some of his oldest.

They were first recorded six years ago, a mission undertaken in his living room, where Haywood-Smith fiddled with his guitar, a borrowed Macbook and the concerns clanging around his brain.

"I honestly didn’t know what I was doing," says Haywood-Smith, who performs and records under the portmanteau JayWood. But that was kind of the point of the DIY project: making do with what he had, figuring out what he didn’t and, over the course of two months, making something — anything — that he could call his.

At the time, the Winnipeg multi-instrumentalist was deep into the musical output of Captured Tracks, an influential Brooklyn label that helped make indie stars out of artists such as Mac DeMarco, Beach Fossils and Wild Nothing. Their sounds were scuzzy, fuzzy, buzzy and a little bit messy, "like it was coming through a Styrofoam cup," he says. JayWood’s early recordings were rushed and "sounded horrendous," but the musical ideas were solid, and he hoped that just maybe, one day, they’d be good enough to earn a Captured Tracks release.

That day, it turns out, is today: JayWood’s single Some Days is being put out by Royal Mountain Records and Captured Tracks, with a digital EP of the same title — containing four songs first conceived in Haywood-Smith’s living room in 2015, plus an acoustic version of the single — due on April 23.

"For me, it’s a full-circle moment," says Haywood-Smith, 27, who’s still shocked and humbled by his own good fortune, especially as it coincides with the pandemic’s destruction and reinvention of the independent music world. "If my former self knew that this would happen, I’d be in disbelief. If my current self brought back some proof, I’d be extremely excited. There were so many times I wasn’t sure I should even be playing."

He kept at it, though. In recent years, JayWood blossomed into one of the city’s best-kept secrets, backed by a bouncy live band that took Haywood-Smith’s music to new heights in concert. The band’s U.S. tour was upended last March when the coronavirus was declared a pandemic: the group had just reached New York City ("It felt apocalyptic there") and had to double back to Winnipeg, where a two-week quarantine at the Roslyn Court Apartments offered Haywood-Smith a chance to plan what was next.

He put together a package of newer material and sent it to Jane Abernethy, the managing editor of Captured Tracks, whom he’d met on the rooftop of the Rialto Theatre at the Pop Montreal festival in 2019 and stayed in touch with since. She really liked his recent album, Time, to Haywood-Smith’s delight, so he mentioned the Some Days work. He’d been playing with the idea of re-recording those songs as a way to reconnect with his old ideas — "going back to go forward" — and before the pandemic, had started some preliminary work on the project at House of Wonders, a local label and recording space.

As it turned out, that preliminary work took months, with the pandemic interrupting the schedule; the EP was finished in the summer. Several months later, it’s finally about to be released into the world, with the label that spurred its creation behind it 100 per cent.

"I like it when a new artist doesn’t comfortably fit into one genre, and Jeremy is not afraid to experiment with style in a way that I find really refreshing," says Abernethy. "I played the unreleased music to our team and to (label founder) Mike (Sniper), and everyone thought he would make a great addition to the Captured Tracks roster."

"Not only is he incredibly talented, but he’s a super-funny and sweet guy," Abernethy adds. "I know he’s going to make the Winnipeg music scene so proud."

The five-song EP is a strong sampling of JayWood’s work: the title track wraps itself around an earworm riff and earnest lyrics ("What do you do when you’re half passed done, when you’re not really sure when your life’s begun"); Creeps shows off JayWood’s unique blend of jazz, funk, psych and indie style; Dreams is built on a foundation of strings ("Getting real strings was special," Haywood-Smith says) and forms the album’s emotional core. The last minute-and-a-half of What You Do To Me is the most fun part of the EP, breaking down into a jam session that will someday make an ideal concert closer.

"Not only is he incredibly talented, but he’s a super–funny and sweet guy." – Managing editor of Captured Tracks Jane Abernethy

And the music video for Some Days — produced and shot by Dog Days Film Company — is a truly wild ride, featuring the live band in supporting roles and Haywood-Smith wearing Spandex as a fitness instructor, lying on the operating table while a surgeon eats spaghetti with Parmesan off his stomach, riding a boat across Falcon Lake, dancing atop a cliff at Birds Hill Ranch, and triumphantly riding a white horse named Shadow through the forest while wearing a shearling jacket and a silver bolo tie.

"Maybe sometimes, you are the cowboy," Haywood-Smith says. "An urban-hipster, Black cowboy, showing out in the middle of nowhere."

Haywood-Smith hopes people enjoy the music, but his hopes extend beyond the reception.

"Being a Black person in the indie scene is obviously an isolating thing," he says. "I hope more people of colour can enter these spaces and challenge preconceived notions of this being white music or a white music scene. I hope people of colour join and rally through this and enter the indie scene, and succeed. Fingers crossed."

As a complete package, JayWood’s latest makes a strong argument for trusting your gut: the songs themselves haven’t changed too much from their bare-bones roots, but with lots of added precision, time and expertise, they’ve become clear indications of an artist from Winnipeg poised to be heard and seen well beyond the Perimeter and beyond the border, a concept a 21-year-old Haywood-Smith would have dismissed as improbable, if not completely impossible, when toying with that borrowed laptop six years ago.

"The coolest response I’ve gotten so far is that these songs sound good by today’s standards," he says. "I knew these were good ideas, but back then I couldn’t get them where I wanted them to be. So it feels really good and incredibly affirming.

"I hope hearing that, maybe folks take time, trust their craft and (are) less harsh on themselves," he adds.

It pays off to believe in yourself.

ben.waldman@freepress.mb.ca