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Musician Kevin Brereton, known by his stage name k-os, is photographed in Toronto on June 25.Jennifer Roberts/The Globe and Mail

Walking down Toronto’s Queen Street West in the fall of 2004, a man shouted a name at Kevin Brereton. Black men in Canada are accustomed to such treatment, but Brereton wasn’t prepared for what he heard. “Hey Crabbuckit!” the man said with a smile. Brereton wasn’t sure if it was the best thing possible or the worst thing, but he knew his life would never be the same.

“Be careful what you wish for,” he thought to himself. He was a grumpy young man wary of fame and suspicious of the music business. No time to get down, though, ‘cause he was moving up.

Brereton is better known as the Trinidadian-Canadian alt-hip hop icon k-os. Crabbuckit is a ridiculously hummable pop hit from his breakthrough album, Joyful Rebellion, which has a birthday later this summer. “Twenty years, man,” he says now. “That’s a person’s life.”

Time flies, and so does the airplane he has to catch later in the day. The Vancouver-based Brereton, 52, spoke to The Globe and Mail in the lounge of the Fairmount Royal York Hotel, where he was staying during a stopover in Toronto. Clad in leather boots, a dark tunic-style top and white cowboy hat (perhaps for a string of DJ shows in Alberta during the Calgary Stampede), he manages to look both distinguished and funky as he sips iced tea and talks about a career-making album that was innovative for its mix of rap, roots, rock and pop.

“The whole concept of Joyful Rebellion was doing things my way and knowing there could be some pushback from it,” he says. “Everything in my life came from that decision.”

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Joyful Rebellion was his second album. In the mid-1990s he had signed a deal with BMG but nothing came out of it. By the time he finally released his first record on another label he was fed up with the industry in general and disgusted by modern rap’s rampant practice of sampling in particular. “I wasn’t going to spend $100,000 or whatever I get on a record deal on other people’s music,” he says.

He eventually released his promising debut album in 2002. It was titled Exit because he planned to quit the business – hello, I’m leaving. “The music industry was not what I thought it would be,” he says. “It was much harder work than I expected.”

In reality, succeeding in the Canadian music business had never been easier. The early 2000s were boom years – Pierre Juneau’s wildest Canadian content dreams from the 1970s had been realized in Technicolor. With grant money for artists from commercial radio and video television flowing and Cancon regulations ensuring airplay, the domestic star-making system had succeeded.

Still, artists such as Brereton and others weren’t comfortable in the machine.

“There was a vulnerability about your position in the natural order of things,” says Juno-winning rocker Sam Roberts, who signed a publishing deal with Universal Music around the same time his friend Brereton did. “It wasn’t necessarily about a mistrust of people. We just wanted to protect our right to make music the way we wanted to make it. That was the fight and struggle that existed at that time.”

When an artist signs a record deal, they know their music will be bled dry – the word “exploited” is typically in the contract. Managing that exploitation is the battle. Brereton’s tactic was to split the difference between what he wanted and what his new label boss (EMI’s late, great Deane Cameron) required.

“Deane was like a father to me,” Brereton explains. “I was going crazy, and he’d call me into his office and tell me, ‘Look, this is what you signed up for. I’m going to make it easier for you, but you have to sell records. That’s what we do, sell records.’”

Brereton made the decision that for every peppy, radio-friendly song he gave the label he’d contribute a thinking man’s song as well. “One for them, one for me,” he explains. “One happy song, one dark song.”

Joyful Rebellion is named for Brereton’s half-and-half compromise. It opens with EMCEE Murdah. Yeah, it’s one of the dark ones, about the evils of the music business (”They want to give you a record deal and then you end up dead”) and how rap music used to be better (”Olden is golden and Black.”)

But it is followed by the upbeat reggae-rock of Crucial and the Michael Jackson-y Man I Used to Be. Then comes Crabbuckit, inspired by the bass line to Ray Charles’s Hit the Road Jack. Brereton wrote it in 15 minutes. Twenty years later, it’s still played on radio and in grocery stores.

“I was blown away when I heard the demos to the album,” says Linda Noelle Bush, who signed Brereton and Sam Roberts to their first publishing deals in the early 2000s. “Kevin was coming to terms with what he had to do and what he wanted to.”

Joyful Rebellion went platinum in Canada, earned k-os three Junos and attracted attention internationally. Rolling Stone’s Christian Hoard wrote that the album “gives alt-rap humanism a good name.” And while Pitchfork’s Derek Miller found the genre-mixing tapestry to be compelling, he felt Brereton was a bit holier than thou.

“He wasn’t wrong,” says Brereton, the son of a preacher.

The Canadian music business today is much different than it was in 2004. Big domestic stars such as k-os (and the Tragically Hip, and Blue Rodeo) were products of a system that has broken down. Streaming has sapped the power of radio, MuchMusic is gone, and Cancon doesn’t mean as much in a music world gone online and international.

“Canadian labels were very focused on Canadian success back then,” Noelle Bush says. “No one was really all that worried about breaking outside of this country, and that just doesn’t work today.”

K-os will perform Joyful Rebellion in its entirety on a tour scheduled to begin next spring. Young concertgoers might be surprised to learn that the concept of a singing rapper wasn’t invented by a certain mansion-dwelling Toronto superstar.

“There’s a collective amnesia that decided that Drake was the first to do it,” says Michael Barclay, author of Hearts on Fire: Six Years That Changed Canadian Music, 2000-2005. “Which is really laughable on many levels, because it negates Lauryn Hill, it negates Queen Latifah, and it absolutely negates k-os.”

Apparently, the collective amnesia doesn’t extend to Drake, who is on board as executive producer for the forthcoming k-os album, Everyone in Your Dream Is You, set to drop late next year. In 2022, Drake organized the All Canadian North Stars, a star-studded gathering of homegrown hip-hop and R&B artists for a concert blowout at Toronto’s History club. There he introduced Brereton as “one of my biggest influences in my life.”

Makes sense. Drake’s cutting-edge rap-and-R&B pop music has antecedents, Joyful Rebellion among them.

“I think a lot of people realized that to have the longest career, you can’t be pigeonholed,” Brereton says. “The thing that I brought to the game that I’m most proud of is the thinking that you don’t have to do just one thing.”

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