The 20 Best Canadian Rap Songs of All Time, Ranked

“If I was somewhere else, I might be doing something completely different. But because of these individuals that performed tonight, I am where I am,” Drake told the sold-out crowd at his All Canadian North Stars show last month. He was referring to a crack team of homegrown hip-hop and R&B OGs—artists like Maestro Fresh Wes, Kardinal Offishall, and Rascalz, who, as Drizzy wrote in his Instagram announcement of the lineup, “paved the way for all of us.” As of this week, The Boy now has 100 top 20 entries on the Billboard Hot 100, more than any other artist in the chart’s 64-year history. Look where he is now.

It’s incredible to see how far Canadian rap has come. A scene that less than two decades ago couldn’t get American audiences to so much as glance its way has birthed an artist who’s bigger than The Beatles. “Back in the ’90s, people would call music ‘Canadian’ as an insult,” Rascalz rapper Red1 said in a 2018 interview. “Like, ‘Yo, I don’t know, that just sounds so… Canadian.’” Nowadays, the word’s a marker of cool. Our artists are the ones people around the world are checking for. 

But the truth is the Great White North has been banging out heaters for a minute. Canada boasts a rich hip-hop history that’s been long overlooked not just by our stateside neighbours, but even by our country’s own media outlets and music industry. While tracks like “Let Your Backbone Slide” and “Money Jane” may not have had as much exposure as “N.Y. State of Mind” and “Hypnotize,” they’re every bit as meaningful and enduring. These are songs that are ingrained in our country’s collective consciousness; songs that created an environment where an artist like Drake, or the next wave of Canadian rappers who came after him, could emerge. So, now that the world’s finally paying attention, it’s a good time to take stock.

To mark Complex’s 20th anniversary, we decided to make the definitive ranking of Canada’s finest hip-hop bangers, old and new. Because someone had to do it, and this country certainly isn’t short on classics. Based on the criteria of quality, cultural impact, popularity, timelessness, and all around slappability, here are the 20 best Canadian rap songs of all time.

“If I was somewhere else, I might be doing something completely different. But because of these individuals that performed tonight, I am where I am,” Drake told the sold-out crowd at his All Canadian North Stars show last month. He was referring to a crack team of homegrown hip-hop and R&B OGs—artists like Maestro Fresh Wes, Kardinal Offishall, and Rascalz, who, as Drizzy wrote in his Instagram announcement of the lineup, “paved the way for all of us.” As of this week, The Boy now has 100 top 20 entries on the Billboard Hot 100, more than any other artist in the chart’s 64-year history. Look where he is now.

It’s incredible to see how far Canadian rap has come. A scene that less than two decades ago couldn’t get American audiences to so much as glance its way has birthed an artist who’s bigger than The Beatles. “Back in the ’90s, people would call music ‘Canadian’ as an insult,” Rascalz rapper Red1 said in a 2018 interview. “Like, ‘Yo, I don’t know, that just sounds so… Canadian.’” Nowadays, the word’s a marker of cool. Our artists are the ones people around the world are checking for. 

But the truth is the Great White North has been banging out heaters for a minute. Canada boasts a rich hip-hop history that’s been long overlooked not just by our stateside neighbours, but even by our country’s own media outlets and music industry. While tracks like “Let Your Backbone Slide” and “Money Jane” may not have had as much exposure as “N.Y. State of Mind” and “Hypnotize,” they’re every bit as meaningful and enduring. These are songs that are ingrained in our country’s collective consciousness; songs that created an environment where an artist like Drake, or the next wave of Canadian rappers who came after him, could emerge. So, now that the world’s finally paying attention, it’s a good time to take stock.

To mark Complex’s 20th anniversary, we decided to make the definitive ranking of Canada’s finest hip-hop bangers, old and new. Because someone had to do it, and this country certainly isn’t short on classics. Based on the criteria of quality, cultural impact, popularity, timelessness, and all around slappability, here are the 20 best Canadian rap songs of all time.