The 20 Best Canadian Rap Songs of All Time
From Drake to Kardinal Offishall to Michie Mee, here's the definitive ranking of Canada’s finest hip-hop bangers, old and new. Because someone had to do it.
Image via Complex Original/Akarts
“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, from coast to coast. 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.
20. Dream Warriors, “My Definition of a Boombastic Jazz Style”
19. Ghetto Concept f/ Maestro, Kardinal Offishall, Red1, Ironside, and Snow, “Still Too Much”
18. Classified, “The Maritimes”
17. Houdini and Burna Bandz, “Late Nights”
16. Dubmatique, “La force de comprendre”
15. Nav, "Myself"
14. Belly f/ The Weeknd, "Might Not"
13. Choclair, "Let's Ride"
12. Jelleestone, “Money Pt. 1”
11. Michie Mee and L.A. Luv, "Jamaican Funk—Canadian Style"
10. Team Rezofficial, “Lonely”
9. Haviah Mighty, “In Women Colour”
8. Rascalz f/ Barrington Levy and K-os, “Top of the World”
7. Baby Blue Soundcrew, “Money Jane”
6. Drake, "Back to Back"
5. K-os, "Crabbuckit"
4. Kardinal Offishall, "Ol' Time Killin"
3. Maestro, "Let Your Backbone Slide"
2. Rascalz f/ Checkmate, Choclair, Kardinal Offishall, and Thrust, "Northern Touch"
1. Drake, “Know Yourself”
Album: If You’re Reading This It’s Too Late
Producers: Boi-1da, Vinylz, Syk Sense
Label: OVO Sound/Young Money/Cash Money/Republic
You cannot transcend what you do not know. To go beyond yourself, the aphorism has it, you must know yourself. Well, on the standout track from Drake’s surprise 2015 mixtape If You’re Reading This It’s Too Late, Canada’s biggest rap export soared to greater heights and brought his city along with him. He did it by distilling the best sides of himself—Introspective Drake, Braggadocious Drake, Singing Drake, Paranoid Drake—into one hair-raising anthem that rechristened Toronto via a tremorous hook: “I was. Running. Through the. 6ix. With my. WOES!” That chorus, featuring Drizzy’s affectionate moniker for his hometown, was unavoidable the year “Know Yourself” dropped, with everyone from Kyle Lowry’s son to pre-slap Will Smith to fans around the globe belting it with their entire chests. It was an instant stimulus package for Toronto’s tourism economy. (But actually.)
Beyond its savvy place-branding, though, the song is a snapshot of Drake’s id during a pivotal moment in his career. In early 2015, with three No. 1 albums under his belt, he still wasn’t getting the respect he was due. Critics continued to argue he was “too soft” to claim hip-hop’s throne, while competitors tried to drain him of his energy, from Diddy fighting him in a club to then-labelmate Tyga calling him “fake” in a VIBE interview. “Niggas want my spot and don’t deserve it,” Drake croon-raps on “Know Yourself.” IYRTITL hears him finally unleash on his haters. The sheepish kid from Degrassi who lint rolls his pants at Raptors games reemerges as a suspicious king who spots signs of treachery everywhere. “Pray the real live forever, man/Pray the fakes get exposed.”
As the stakes rise, Boi-1da’s ice-cold, jittery production swells with intensity and Drizzy’s cadence quickens; a master class in tension-building. The track then halts before ascending to a higher plane of existence; Drake, as if mid-revelation, bellows the now-iconic hook over a twinkling instrumental that sounds something like an ice cream truck careening into a black hole. This will go down as one of the hardest drops to ever grace a rap record. Whenever it hits, strangers in bars, regardless of culture or creed, start mosh pits and scream about mobbing through Toronto with one’s confidantes. It’s a triumphant moment—Aubrey finds sanctuary in his pre-fame community, resisting outside pressure to become something he’s not.
“I told myself, over the duration of my career, I would definitely have a song that strictly belonged to Toronto, but that the world embraced,” Drake said in a 2015 interview with The FADER. That song was “Know Yourself,” which, despite its un-hit-like structure, cryptic patois interludes, and hyper-local references, immortalized the 6ix in hip-hop lore and ushered in an era of Cool Canadiana. Rappers and producers from the city (and the country) now get more attention than ever, and aspiring Canuck artists have a legend to idolize. With IYRTITL, Drake set a new record for most songs on the Billboard charts simultaneously, cementing his megastar status. Yes, he’d go on to have more slaps than the Beatles, but this was his turning point. It’s when he learned how to best handle his detractors: by doubling down on who he was and where he came from, even if some people didn’t get it. Soon enough, the world would catch up. —Alex Nino Gheciu