top of page

Toronto Hip Hop Icons, Rappers Who Marked The City's Scene History

The top Toronto hip-hop acts to highlight just how diverse and underappreciated Canada's hip-hop scene is. Being Canada's major metropolitan center, it's no wonder that many of the country's hip hop bigwigs come from Toronto.

While there were some evident choices, it's not easy to make a list like this in any genre of music. The criteria for inclusion here were an act's historical importance, the success of their songs and projects based on sales and critical acclaim, and their capacity to make it through into global markets.


No rapper represents Toronto better than Drake - the most current notch on that belt being his international ambassadorship for the Raptors. Aside from the great business movies, his musical skill and impact on hip-hop are indisputable. At least three of his albums have gone platinum and peaked at number 1 on Billboard and he bears the record for most number 1 hits on the Billboard Hot Rap Songs chart. He's been selected for 13 Grammys and won one, plus numerous BET awards and 6 MuchMusic Video awards.

People who doubt whether Forest Hill forms "the bottom" fail to recognize Drake's speaking about his career. He rocketed from zero and has seen everything. All signs indicate Drake sticking around for a while... so get used to it!

Maestro Fresh Wes

It would almost be easy to undervalue the significance of Maestro on this list, given the power of Toronto's hip-hop community today.

It was another story back in 1989 when he dropped "Let Your Backbone Slide," a song that made the top 40 which was exceptional for the Canadian hip hop scene at the time. Much of the 1990s were less friendly to Maestro, but he's born to being a Toronto hip hop example and an ambassador for the community since releasing the Black Tuxedo in 2012. Drake might be the international representative boy for the Toronto hip hop scene, but Maestro is, well, the backbone of the city scene.


One of Toronto's most notable hip-hop icons is rapper, singer, and producer Saukrates.

In 1994 Capitol Hill dropped his known popular Brick House EP, featuring Common, O.C., and Masta Ace. This was conducted to full length, The Underground Tapes, and cooperate with Choclair, Pharoahe Monch, Xzibit, and Heltah Skeltah. He caught his second Juno nomination for "Money Or Love", had a song on the soundtrack for Red & Meth's "How High," and produced "Heaven" on Nas' God's Son.

In '06 he performed considerably with Nelly Furtado, working with her at the 94th Grey Cup, the American Music Awards, and on her "Get Loose" tour.

He's still an associate of Redman's Gilla House group. Last year Saukrates dropped its sophomore album Season One, featuring production by Rich Kidd and appearances by Redman, Nelly Furtado, and k-os.

Kardinal Offishall

Born in Scarborough, Kardi is liable for more than just popularizing the term T-dot. His career began off on an amazing note - at age 12 he performed his first show to an audience including Nelson Mandela.

Kardinal's dancehall reggae-influenced technique was adopted globally, allowing the world to see Toronto as the multicultural center that it is.

He worked with Sean Paul, the Baby Blue Sound crew, the Rascalz, and, in 2005, Akon who he would eventually sign onto his Kon Live Distribution label.

In 2007 his track "Dangerous" took it to the top five hits on the Billboard Hot 100 chart and reached triple platinum in Canada.

Ghetto Concept

Coming from Rexdale and Lawrence Heights, this duo was most dynamic in the 1990s, winning two Juno awards for their songs "Certified" and "E-Z On Tha Motion", respectively. Although they started in 1989, the duo wouldn't drop their debut album until 1998. It was well credited, but their most widespread track didn't come until 2001, in the form of "Still Too Much" a remix featuring Maestro, Kardinal Offishall, Red-1, and Snow.


Born in Scarborough, Choclair aka Chox or Chiznock would have a major influence on Canadian hip hop. After mounting the strings in the underground he dropped his What It Takes EP in 1997. Two years after his first full-length, Ice Cold would be classified as a Canadian classic.

Off the power of the Kardinal Offishall-produced track "Let's Ride," the album would market over 50,000 copies and win a MuchMusic Video award, a Juno Award, and a SOCAN award. Choclair's place in Toronto's hip hop scene is set in stone forever.


bottom of page