1. Rascalz
In the early 90s, Vancouver's Rascalz gained underground attention with a debut Really Livin'. But in 1998, their studio debut proper Cash Crop brought Rascalz into the Canadian music mainstream. Winning Best Rap Recording at that year’s Juno awards, Red1, Misfit, and DJ Kemo refused it when the category wasn't aired during the televised ceremony.
The following year, Rascalz won the same category again. Their now-legendary performance of "Northern Touch" (the country’s first truly huge homegrown hip-hop hit) with guests Checkmate, Kardinal Offishall, Thrust, and Choclair in tow broke barriers for Canadian hip-hop on live TV. Their album Global Warming produced further hits like "Top of the World" featuring Barrington Levy and K-os and cemented their influence on Canadian hip-hop. Beyond their own classic contributions, Rascalz helped launch careers that would change the face of Canadian hip-hop in the new millennium.
2. Kardinal Offishall
From the late 90's, well into the next decade, Toronto's Kardinal Offishall played an unprecedented role in propelling hip-hop in Canada toward commercial success and pop culture credibility. His 2000 hit single "BaKardi Slang” introduced the world to the term “T-Dot” beyond his city and past international borders. Subsequent singles, including “Dangerous” in 2008, drove respectable album sales at home and in the US. And it can be understood that the advent of widespread music piracy earlier in the decade didn’t hurt his popularity, either.
Kardi’s blend of reggae and rap influences helped put some shine on the concept of hip-hop as a viable export to a US market that had always been just out of reach for Canadian talent. Collaborations with American artists, including Busta Rhymes, Akon and Rihanna, served as bankable proof. At home, Kardi helped set the table for breakthroughs from the likes of Sean Paul (an honourary Canadian if you watched Much Music back then), Jully Black, Saukrates, and Choclair.
3. Baby Blue Soundcrew
The Toronto DJ collective helped open the door for Canadian hip-hop talent to be taken seriously here at home, if not elsewhere. Despite early attempts to achieve the credibility of hot artists in the US, (if not the commercial success) that seemed to come easily in New York, LA and the emerging “Dirty South” movement, fame remained elusive for Canadian artists until our own sense of identity in the genre began to achieve maturity. During their prolific heyday, what Baby Blue Soundcrew did well (and why they mattered more than many really realized, beyond making slick videos) was to put hip-hop back in the hands of the DJs. At the beginning of the millennium, having one artist at a time drop a single and a video into rotation on MuchMusic and praying like hell was not a strategy that was going to help Canadian artists compete. But positioning artists like Choclair, Jully Black, and Baby Cham alongside Kardi on mixtape compilations featuring the big name US hitmakers like Dr. Dre, Nas, and Jay-Z and releasing them as albums was a masterstroke. BBS basically took the Big Shiny Tunes model and put some hip-hop savvy on it as a band that was really a brand.
4. Swollen Members
Though their roots extend to the very beginning of the 1990's, the Vancouver duo truly achieved national prominence at the dawn of the new millennium, when underground hip-hop and skate punk cultures found common ground at Hot Topic stores and at Warped Tour venues around the continent by way of mutual appreciation for Eminem. Prevail and Madchild’s 1999 debut, Balance, fed their metal cosplay vibe to an audience hungry for an alternative to the pop hip-hop heard on car stereos and in clubs. Songs like “Lady Venom” were truly of their time, and Balance featured a who’s-who of established and emerging LA hip-hop players like Evidence, the Alchemist and Del tha Funkee Homosapien. Their own label, Battleaxe Warriors, mirrored the West Coast indie rap scene north of the 49th parallel. Swollen’s 2001 sophomore Bad Dreams birthed the aptly-titled hit “Fuel Injected,” and featured on-and-off member Moka Only on its classic hook.
5. Buck 65
The raspy-voiced Halifax rapper truly entered the stage with his 2003 major label debut Talkin’ Honky Blues. A Beck-aping single, “Wicked & Weird,” caught mainstream airplay across Canada on the strength of its novelty. But Buck was no newcomer. Known in Halifax as college radio DJ Critical, later as producer/DJ Stinkin’ Rich, and then as half of weirdo rap duo Sebutones with Sixtoo, Buck 65 was an established factor on Canada’s East Coast hip-hop scene and the nationwide underground, with five albums out on various indie labels from ‘96 onward. His 2001 Anticon release Synesthesia positioned Buck 65 as Canada's bridge to the brimming indie rap scene south of the border. Today, he's widely known as CBC Radio personality Rich Terfry. But Buck 65 still gets down when he gets the itch, and he remains an example of longevity in Canadian hip-hop.
6. Cadence Weapon
There’s a parallel world where Edmonton-born MC and producer Cadence Weapon claims pole position in Canadian hip-hop before anyone’s ever heard of Drake. But in this timeline, the role he plays not only as a musical artist but as an outspoken figure for Canada’s artistic and cultural communities is meaningful. Having claimed Edmonton, Montreal, and Toronto as home at various points throughout his career, Cadence Weapon’s most important contribution to Canadian hip-hop may be the versatile, cross-scene agility he wields as a networking force within the larger national music scene. A boundary-pushing production style has been his superpower since dropping his 2004 debut, Breaking Kayfabe, at age 19. His latest, 2021’s Parallel World, won that year’s Polaris Prize. And yet somehow, it still always feels like Cadence Weapon is still just getting started.
7. K-os
Informed by the lyrical mastery of Golden Age rap gods and inspired by the constant experimental evolution of sounds and samples that hip-hop’s first wave of introduced to its growing audience, Toronto’s K-os rose to prominence early in the millennium with an advantage.
By then, the genre was much more widely accessible to a broader range of fans and styles had long since shifted from the street to the club, from mixshows to MTV of hip-hop music. K-os (an acronym for “knowledge of self” and a nod to lyrical giant KRS-One) capitalized on an era that was ripe for reinvention and an audience that was open-minded to hip-hop while at the same time frustrated by seemingly generic artists dominating the charts.
Fusing live instrumentation with studio production, each new K-os record brought more fans to the fold. His first LP, Exit and its buzzed-over single “Heaven Only Knows” set the stage. His next album, Joyful Rebellion, generated a mainstream radio hit with “Crabbuckit” alongside anthems “B-Boy Stance" and “Love Song.” His third album, Atlantis: Hymns For Disco, spawned another pop staple: “Sunday Morning." And in 2009 successor, Yes! delivered another big tune, “I Wish I Knew Natalie Portman,” and featured Saukrates and Nelly Furtado. Pound for pound Canadian rap’s most consistent hit maker prior to 2010, and his boundary-breaking impact remains game-changing at home.
8. Bad News Brown
Certainly one of the more tragic figures in Canadian hip-hop history, Montreal’s Bad News Brown (born Paul Frappier) played a pivotal role in the advancement of the music and culture of hip-hop. True to the roots of the culture, BNB married talent, ingenuity, and accessibility to first make his name as a busker. Playing harmonica in metro stations across Montreal’s public transit system, he was instantly recognizable to literally hundreds of thousands of regular commuters. On stage, News combined live elements, beats, his harp, and rap skills to forge a reputation as a true entertainer. As such, he was often invited to join headliners like De La Soul, Nas, and Ice T on stage with his harmonica. At home, he helped unify the province’s English and French language hip-hop scenes, inviting talented rappers and producers to his studio. His heavy touring schedule and collaborations helped build inroads to Toronto and LA, and his supportive nature helped many artists build their own networks outside of Quebec. Released in 2009, his only studio project, Born 2 Sin, captured Bad News Brown’s vast range. Its eponymous first single is a lowkey Canadian hip-hop classic. A second single and video, the melancholic, harp-heavy “Reign,” endures hauntingly. In early 2011 at age 33, Bad News Brown was found dead in a Montreal alley, the victim of a still unsolved suspected murder.
9. A-Trak
Younger generations of festival-goers and electronic music fans are likelier to recognize the Montreal-born DJ for his high profile in the EDM world. But take it back to when DJ skill competitions and their champions enjoyed cult status, and there was Trizzy. At age 15, in 1997, his world DMC title jumped off a career that soon found him busy in New York and LA. In ‘99, a seven- inch single, “Enter Ralph Wiggum,” was among the earliest releases on Stones Throw Records, home to Madlib and later J Dilla. Flash forward a few years, and A-Trak was on DJ duties for Kanye. His cuts featured on “Gold Digger,” among others, and his Expos cap became a fixture on tour stages. In 2007, he co-founded Fool’s Gold. The label earned near-instant credibility, and A-Trak’s status as an influencer grew. Never too far behind, his big brother Dave-1 (a Montreal hip-hop scene vet and columnist during the heyday of Vice) was making noise with 80's funk revival outfit Chromeo. The next decade saw Trizzy putting on the likes of Kid Cudi, Danny Brown, and Run The Jewels, and teaming up with rave culture legend Armand Van Helden for Duck Sauce. As his accomplishments continue to shine from afar, A-Trak is still a Montrealer at heart.
10. K'naan
He may not be the first name that comes to mind, but it would be impossible not to include the Somalia-born singer/songwriter and MC on a list of Canadian hip-hop notables. Having arrived in Toronto by way of New York at age 13, escaping violence and civil war in his native country, K’naan truly represents Canada as an international artist. His take on hip-hop as a storytelling medium and a vehicle for social awareness combined with a pop songwriting sensibility birthed the mega-hit “Wavin’ Flag.” That song in turn married commercial viability and a powerful message, boosting K’naan to global recognition when Coca-Cola adopted it as their promotional anthem during the 2010 World Cup. While K’naan’s mark on Canada’s larger hip-hop landscape may be limited in scope, “Wavin’ Flag” reached heights that only the marketing machine of American ingenuity can aim for. And so was set the tone for the coming decade, when Canadian hip-hop talent would finally wave its own flag around the world.
