As a teen, Jesse Bedard Dempster wasn’t that different from a lot of city kids harbouring hip-hop hope: he and one of his best friends would wander Scarborough, swapping rhymes and mapping out a future that seemed infinite.
The difference, however, is that Dempster’s aforementioned close friend and partner-in-rhyme was a fresh-faced Ethiopian-Canadian kid named Abel Tesfaye — the same singer who would soon ride sumptuous bad vibes straight to the top as the Weeknd.
Back then, Tesfaye (or Kin Kane) and Dempster (then JesseRay) comprised the rap duo Bulleez N Nerdz. Just starting out, they were fledgling and fumbling, yes, but they were also sort of onto something; and estranged though they are now, Dempster can only marvel at what his former partner has accomplished.
“Imagine if you were in my shoes and one of your old buddies is now seven-Grammy-nominated, and you literally know this guy didn’t have five bucks in his pocket a couple years ago,” Dempster said. “He bought his mom a house. It’s so inspiring.
“I remember talking to him about how Toronto’s almost a joke and how he wanted to change the whole Toronto scene. And it’s weird, because he actually did it.
“It’s just crazy to me,” he continued, “because I just feel like my time is there, too.”
Where Tesfaye’s obscurity-to-Oscars story is the stuff of Hollywood screen dreams, Dempster’s own circuitous path has the feel of, well, reality.
Dempster began rap-battling at 14, a couple of years before he met Tesfaye through friends and recognized a common interest in music. At the time, Tesfaye was “rolling with a rough crowd” and the two were each drifting away from school and home. “We were doing stupid things,” Dempster said.
Well, music and mischief were intertwined. Dempster recalls one aimless night downtown when the duo missed the last subway home. With less than $5 between them and no one at home to foot the taxi fare back to Scarborough, they wandered across the city to a Tim Hortons, where they spent the night writing rhymes.
Dempster fondly recalls Tesfaye’s goofy sense of humour, his ability to impersonate “any show, any character.” He remembers Tesfaye cruising up to a McDonald’s drive-through speaker and, with a perfect Hank Hill lilt, ordering propane accessories.
“He’s one of the funniest people I know,” Dempster said. “Kind heart, takes care of the people around him. He did grow up very poor. He always wanted to not be home. I left home at an early age too, so there are nights we stayed out on the street together.”
Musically, they were inspired by the genre-jumping audacity of Pharrell Williams — hence their group name, perched between swagger and self-deprecation. Dempster sometimes strummed an acoustic guitar and rapped while Tesfaye sang; they called the side pursuit Regretful Tattoos. Tesfaye was a reluctant singer but talked about making “dark R&B.”
They recorded a few songs and gingerly entertained interest from management types. Their chemistry worked onstage, too; Dempster recalls their last performance, at the former Nile Bar, when they won over what seemed like a reggae-leaning crowd with “Godzilla.”
Just as quickly as they grew close, however, they drifted apart. One of Dempster’s friends committed suicide and he went into a deep, alienating funk. “I wasn’t making music. I wasn’t talking to anyone. I was in this depressed state.”
Meantime, Tesfaye moved into a rental in Parkdale and found his voice. The first time Dempster heard Tesfaye’s first mixtape, House of Balloons, he knew instantly it was his old friend. Aside from a chance encounter, they haven’t seen each other since.
But even in absence, Tesfaye has loomed large for Dempster. Only after seeing his friend succeed did Dempster feel motivated to start making music again. Since, he’s been burned by bad luck and bad business.
His debut album, 1990, is unavailable due to a falling out with his old manager. He’s worked various jobs, as a waiter, as a water-park safety inspector and now at a marijuana dispensary downtown. He’s released several videos and assembled quite a social-media following, but he worried fans were drawn only to his association with Tesfaye, so he changed his handle to Nixxon.
And yet, distance hasn’t dimmed Dempster’s view of Tesfaye.
“I know he’s the same guy. People say money makes you change, but he doesn’t change.”
But Dempster, now 25, has; he’s more dedicated now. He’s stockpiled more material than a textile mill and soon plans to release the new album For No Good Reason alongside a re-released 1990.
Some might be bitter to see their former wingman soar solo, but Dempster looks at Tesfaye’s stardom and seems to find genuine joy — and, perhaps more importantly, inspiration.
“He showed me, almost, how easy it is. I know that sounds crazy,” Dempster said.
“But being so close to him and seeing what happened to him, and how much he doubted himself at times, opens so many doors for me. It’s there. It’s just an arm’s reach away.”