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2. Saukrates
Years active: 1994 - present
Hometown: Toronto, Ontario
Saukrates may be one of the most influential hip-hop figures in Canadian hip-hop. Since making his debut in '94 with "Still Caught Up" (which was nominated for Best Rap Recording at the '96 Junos), Saukrates also found success as the leader of Big Black Lincoln, as well as working closely with Redman and Method Man. Having released multiple LPs and mixtapes, the MC is also the co-founder of Capitol Hill Music, an independent record label that Saukrates created with his manager, Chase Parsons. The label, in fact, is in a way responsible for Kardinal Offishall's eventual fame, as it released Kardinal's debut album, creating a sturdy foundation for the rapper.
3. D-Sisive
Years active: 1990s - present
Hometown: Toronto, Ontario
Like many of the rappers featured on this list, D-Sisive began his rise to prominence during the '90s in the Toronto hip-hop scene. But what inspires him is slightly darker than that of his peers. Between 2001 and 2007, Derek Christoff took a six-year long hiatus due to his battle with depression, following the death of his mother in '01, and his father in '07. When he finally decided to make his return, D-Sisive came back triumphantly with The Book EP, which really gives listeners some insight as to how he was dealing with the death of his parents. It's this type of incredibly honest and personal narrative expressed through his rhymes, not to mention consistently stellar beats and poetic lyrics, that sets D-Sisive apart as one of the greats.
4. Mcenroe
Years active: 1991 - present
Hometown: Brandon, Manitoba
mcenroe isn't a household name, but he's somewhat of a legend for what he's done for the Canadian independent hip-hop community. In 1994 he founded Peanuts & Corn Records and has promoted and produced for artists like Pip Skid, John Smith, fermented reptile, and his own groups Farm Fresh and Park-Like Setting. Instead of going for mainstream success, mcenroe stuck to his principles and built a solid following based on a unique set of aesthetics.
5. Choclair
Years active: 1995 - present
Hometown: Scarborough, Ontario
Rapping runs in Choclair's family. Kareem Blake began his career at the age of 11, following in the footsteps of his older brother. After years of honing his skills, and releasing 11 records, Choclair received acclaim for his work with The Rascalz on "Northern Touch," often dubbed as Canada's hip-hop anthem, and received numerous awards. In the early 2000s, he went to start his own label, Greenhouse Music, in partnership with Sextant Records and EMI Music Canada, providing other Canadian hip-hop artists the opportunity to share their craft. Evidently, Choclair has made a mark, not only through providing Canada with hip-hop during a time when it was scarce, but also through giving back to the hip-hop community through his label.
6. Sixtoo
Years active: 1990 - present
Hometown: Halifax, Nova Scotia
Vaughn Robert Squire has taken on many guises over the years (Speakerbruiser Rob, Prison Garde, etc.), but much of his musical career has been dedicated to his hip-hop alter-ego, Sixtoo. He was heavily involved in the underground hip-hop scene in Halifax, Nova Scotia in the mid '90s, performing as one half of Sebutones alongside Buck 65, and he also worked closely with Sage Francis and other members of Anticon.
When he decided to leave Halifax in 2000, it was then when he would start experimenting with the sampler. This machine would ultimately influence his style thereafter as he shifted from rapping on the mic, to solely sampling live musicians (and other sources), as evidenced by his 2004 LP, Chewing On Glass & Other Miracle Cures. Eventually, Squire retired Sixtoo in 2007, but he's still actively experimenting with electronic music, and considered as one of the pioneers of incorporating the sampler in the Canadian hip-hop world.
7. Moka Only
Years active: 1989 - present
Hometown: Vancouver, British Columbia
To say that Daniel Denton, better known as Moka Only, has had a fruitful musical career would be a huge understatement. From being a part of Swollen Members to working with Souls of Mischief, Moka Only has made the most out of his 23 years in the game as one of the first Canadian hip-hop artists. This isn't surprising when you consider his signature laidback aesthetic, smooth-as-butter flow, and lyrical mastery. It may also explain the 66—yes, 66—albums that he's released as a solo artist, as well as collaboratively.
8. Madchild (of Swollen Members)
Years active: 1992 - present
Hometown: Vancouver, British Columbia
As a duo, Swollen Members (Madchild and Prevail) earned themselves a spot as underground heroes in the early 2000s. While Prevail provided a more grounded, straightforward delivery, Madchild's battle rap background gives every verse he spits some sharp teeth and a strong bite. Steering clear of the typical hip-hop image, Mad Child seems more like Canada's resident rockstar rapper, steadily pumping out the kind of high intensity flows fit to soundtrack extreme sports events sponsored by Monster energy drinks.
9. Buck 65
Years active: 1993 - present
Hometown: Mt. Uniacke, Nova Scotia
Buck 65 (born Richard Tefry) is a restlessly creative rapper, producer, and DJ who has honed and perfected his alt hip-hop sound during a career of nearly 20 years, during the course of which he has released music with some of forward thinking rap music's most interesting names, including the Anticon collective and Sage Francis. As well as underground acclaim, Buck 65 has experienced some measure of mainstream success, with his older music being re-released by Warner in Canada, not to mention his hosting of the weekday Drive show on CBC Radio 2 since 2008.
As his career has progressed, Tefry has incorporated more and more non hip-hop elements into his music, especially on 2005's Secret House Against The World, but whether he's rapping over classic boom bap beats or the hazy electronic soundscapes of Belgian producer Greetings from Tuskan (who he collaborated with as Bike For Three!), Buck 65 always brings razor sharp lyricism and a heavy helping of self-awareness to his music.
10. Maestro
Years active: 1987 - present
Hometown: Toronto, Ontario
When it comes to Canadian rappers, no list goes without mentioning Maestro. Often referred to as the Godfather of Canadian hip-hop, he was the first Canadian rapper to attain a Top 40 single with "Let Your Backbone Slide." Despite the fact that he had difficulty achieving the same level of success in the U.S., his debut record, Symphony in Effect, is still one of the best selling hip-hop albums of all time in Canada. In many ways, he paved the way and laid down the foundation for future Canadian hip-hop artists, as when he started out in '83, Canadian hip-hop was essentially non-existent. You can thank Drake later, but Drake can thank Maestro now.
11. Classified
Years active: 1995 - present
Hometown: Enfield, Nova Scotia
Classified released his first album in 1995, and for almost two decades he's been steadily releasing music, building a resume that boasts 15 mostly self-produced studio albums and plenty of appearances on the Canadian charts. Most recently, he was certified Platinum for "Inner Ninja," and even if he never goes completely mainstream in the U.S., he's already secured a spot as one of Canada's most successful and prolific rappers ever.
12. Cadence Weapon
Years active: 2005 - present
Hometown: Edmonton, Alberta
Cadence Weapon has been releasing music since 1995, but he's come into the spotlight recently thanks to co-signs from fellow Canadian musicians like Grimes. Cadence Weapon's father was a DJ, and he's stated that electronic music has always been a big influence on him. He was also the poet laureate of Edmonton and used to contribute to Pitchfork, and while these things may not be apparent in his music, they offer some insight into what separates Cadence Weapon from the flocks of hip-hop heads turned rappers. One of the most intelligent and creative to come from Canada, Cadence Weapon seems to be gaining momentum with every release and establishing himself not just as a rapper's rapper, but as a true artist.
13. K'naan
Years active: 2001 - present
Hometown: Toronto, Ontario
K'naan was born in Somalia but moved to Canada as a teenager. His roots play a powerful role in shaping his message and his perspective, and even though he saw massive international success with tracks like "Wavin' Flag"—which became the official theme song to the 2010 FIFA World Cup—he's voiced his desire to stay true to himself as an artist in this convincing open letter. Also a musician capable of crafting songs that stretch beyond rap, K'naan is one of the most engaging, talented, and versatile hip-hop artists to come out of Canada in the past decade.
14. Shad
Years active: 2005 - present
Hometown: London, Ontario
Shad's humble beginnings may explain his signature self-deprecating lyrics. While he was completing his undergraduate degree at Wilfrid Laurier University in Waterloo, Ontario, Sharach Kabango entered a local radio station's talent competition and won $17,500. With that money, he made and released his debut album, When This Is Over, and promptly hit the road to share his music. He quickly achieved fame across Canada, eventually winning the Juno Award for Rap Recording of the Year in 2011 and he's still going strong and continuing to build his strong a loyal fan base.
15. k-os
Years active: 1993 - present
Hometown: Toronto, Ontario
k-os released his first single in 1993, and shortly after he dropped out of college and started getting attention within the music industry. Within a few years, he stepped out of the spotlight and later explained that he wasn't happy with the direction of his music. It wasn't until 2002 that he ended up dropping his debut album. Always employing sounds and styles from pop, rock, and electronic genres, k-os found his place in hip-hop as not only one of the most eclectic and creatively forward-thinking rappers, but one that could balance his artistic integrity with mass appeal. Several of his albums have gone platinum in Canada.
16. Kardinal Offishall
Years active: 1996 - present
Hometown: Toronto, Ontario
Depending on which Kardinal Offishall song you're listening to, you would be forgiven for thinking that the rapper and producer is a dancehall artist from Jamaica or a Flo Rida-esque pop rapper from America. This potential for confusion is testament not just to Jason Harrow's Jamaican descent, but to his extreme versatility in the studio, which explains how he has managed to have a pretty corny Billboard 100 top 5 hit ("Dangerous," featuring Akon) but also remained critically respected.
Having released music with MCA and Geffen, and worked with hip-hop stalwarts like The Clipse and Boi-1da, Kardinal is one of Canada's most successful exports, and, prior to Drake, somewhat of an ambassador for glossy Canadian hip-hop.
