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.

The 20 Best Canadian Rap Songs of All Time
Complex Original

Image via Complex Original/Akarts

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, 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”

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Album: And Now the Legacy Begins

Producer: Dream Warriors, Maximum 60

Label: Island

Released: 1991

Before there was Austin Powers, there was “My Definition.” (And even before that, there was CTV game show Definition.) “Soul Bossa Nova” by Quincy Jones isn’t necessarily the easiest sample to jump on to, but then-dynamic duo King Lou and Capital Q always marched to their own beat. At a time when Canadian hip-hop was just finding its rhythm, the Toronto pair’s debut album And Now the Legacy Begins found breakthrough success in both the UK and Europe by flipping the script and doing its own thing.

It’s no surprise “My Definition” found an audience, starting with that unmistakable Quincy sample. Jazz-inspired rap was just taking off down south and the pair cracked the code of how to effortlessly combine styles, making the perfect entry point for reticent newcomers and golden-era rap aficionados alike. The song is ostensibly an unfollowable how-to for their undefinable, cosmic approach, right down to the gold canes over gold chains.

The first Rap Recording of the Year Juno Award was given out a year prior to Maestro Fresh Wes, and Dream Warriors claimed the second. As with the former’s first hit single, it’s impossible to envision Canadian rap lore without “My Definition” serving as a gateway. —Erik Leijon

19. Ghetto Concept f/ Maestro, Kardinal Offishall, Red1, Ironside, and Snow, “Still Too Much”

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Album: N/A

Producer: Stuntman

Label: BMG

Released: 2002

Toronto’s Ghetto Concept occupies some extremely rare territory in the landscape of Canadian hip-hop: hugely influential, revered among those in the know, and yet still somehow wildly underrated and obscure. The legendary duo of Kwajo Cinqo and Dolo, hailing from the city’s Rexdale and Lawrence Heights neighbourhoods, started blowing up on the city’s underground rap scene in the very early 1990s, and you’d be hard-pressed to find a contemporary Canadian rapper who doesn’t cite them as an early influence. But it’s “Still Too Much,” the star-studded (by Canuck standards, anyway) remix of their hit single “Too Much,” that really has emerged as their biggest certified classic. An upbeat, propulsive banger that feels very much of a piece with the style of early 2000s hip-hop, “Still Too Much” brings together such celebrated countrymen as Maestro, Red1, Kardinal Offishall, and yes, even Snow, for a collaborative work with the collective power of a bona fide supergroup. It’s a hit that remains an unimpeachable Toronto anthem. —Calum Marsh

18. Classified, “The Maritimes”

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Album: Boy-Cott-In the Industry

Producer: Classified

Label: Halflife Records / Fontana North

Released: 2005

Aside from cheekily dismissing stereotypes about Canada’s criminally overlooked East Coast—be it never trying lobster or not knowing how to play the fiddle—Classified’s early hit also broke sonic ground. Its Celtic riff captured the essence of traditional Maritime music, but was lilting enough to sound winking and anything but self-serious. It was also distinctive and catchy as all get-out. As an instrument, it’s a bit tough to pin down, and when asked about it Classified told Complex Canada: “It’s funny ‘cause when I made the beat, I thought it was a bagpipe and thought it fit great with the theme of the song. Over the years, I realized it was an accordion.” Regardless, the sample suited both the song and the artist who would go on to break through nationally, though by then many Canadian rap fans already loved “Maritimes” because of its endearing animated music video’s heavy rotation on Much Vibe.

And no, Class didn’t record a stereotypical East Coast kitchen party for that one-of-a-kind sample. Instead, he found it by digging through records at the Salvation Army, where he would usually purchase any vinyl under a loonie. He adds: “Definitely was a unique record to dig for samples from. But it worked out.” —Kyle Mullin

17. Houdini and Burna Bandz, “Late Nights”

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Album: Northside Jane

Producer: HirstBeatz

Label: UpTopMovement Inc and Blue Feather Records

Released: 2018

While it would go on to rack up over 11 million YouTube views, “Late Nights” by Houdini and Burna Bandz immediately made a case for itself as a classic Toronto hip-hop track from the moment it dropped. It possessed every element we look for, and the sound we seem to want representing our city: ominous lyrics, Gothic synths, and a chorus that burrows into your cerebrum. To this day, Jane and Finch’s north side holds a mysterious allure to outsiders, and its fair to say a major part of that is owed to the way “Late Nights” put a viral face and sound to a neighborhood so infamous and referenced throughout local pop culture. Trading melodically beguiling verses, the two young rappers speak candidly about the ongoings of their evenings, referencing Hurontario’s 5 and 10 and the nocturnal routine of their lifestyles: “Cruisers, cruising/Fourteen on the strip with a rubben/These times, I was just a minor/Outta town, don’t tell my guardian.”

Houdini’s life would be cut tragically short in 2020, and this song will forever be a time capsule of his seemingly limitless potential. “I’m still making my way. Like, I never peaked yet, you know? I’m still finding my sound. I’m still trying to see how I can elevate,” he told Complex Canada in 2020. There’s a reason he continues to be one of the most streamed independent rappers in the city. Part of what made Hou so promising, beyond his prolificity, was the way he took control of his own story, and the stories of his brethren, whether it was considered respectable by societal standards or not. —Yasmine Duale

16. Dubmatique, “La force de comprendre” ​​​​​​​

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Album: La force de comprendre

Producer: DJ Choice

Label: Les Disques Tox Inc.

Released: 1997

It’s impossible to understate the importance of Dubmatique’s rise on Quebec’s cultural landscape. In 1997, the trailblazers were the first Montreal rap act to conquer their hometown, moving 100, 000 copies of their landmark debut LP. You couldn’t escape the trio, as their videos were plastered all over MusiquePlus and their shows got more and more hyped. Their breakthrough even forced the ADISQ awards to create a rap category. If anyone created the template for success in rap in Quebec, it’s Dubmatique, and the contemplative call-to-consciousness “La force de comprendre” was one of their two anthems that established Montreal’s love of hip-hop.

Inspired by MC Solaar blowing up in France and conscious rap rising on the East Coast, the well-travelled MC duo Disoul and OTMC had the perspective and know-how to break through here in their native tongue even though it hadn’t really happened for anyone else yet. It’s a coin flip as to whether the album’s title track or smoother opener “Soul Pleurer” is more iconic, but the former gets the nod thanks to Dessy De Lauro’s unforgettable hook that perfectly captured the energy of the moment created by in-house producer DJ Choice. Both singles set the bar for Quebec rap and one could make the case they’ve yet to be surpassed. —Erik Leijon

15. Nav, "Myself"

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Album: The Introduction

Producer: Nav

Label: XO Records and Republic Records

Release date: 2016

Something must’ve been added to Toronto’s water supply in 2016. I have some theories, but the city’s sudden rise of DIY SoundCloud rappers and YouTube sensations organically cultivating devoted listeners with nonexistent overhead costs tested the limits of the Internet-age artist and made what was once exclusive incredibly accessible.

At his mother’s home in Rexdale, Nav produced, wrote, sang, and recorded a confessional song about self-medication that would become a runaway hit. On paper, the lyrics to “Myself” sound downright depressing: “Drivin’ solo, I’m just swervin’ through my ends/When I’m sober I just don’t like who I am/Pour me up a four and I’ll feel like myself again/Roll me up some dope and I’ll feel like myself again.” But over a soft-hued trap beat and delivered in the Punjabi-Canadian’s sing-song flow, it sounds about as intoxicating as the narcotics he raps about. While Nav began his career as a producer, co-helming Drake’s “Back to Back” in 2015, “Myself” was when he’d first enjoy mainstream success, with Kylie Jenner even posting the song on her Snapchat. The rest is history: he’d fall in with XO and continue doing insane numbers, releasing two consecutive No. 1 albums and becoming “the first brown boy to get it popping.”

Today, Nav is one of the most successful Canadian hip-hop artists alive, carving a path for others who may not look like what some consider a ‘typical rapper’ in mainstream pop culture. “The portrayal of my people can be unfortunate,” he told Complex in a 2020 interview. “I feel like the last real representation of us in pop culture is like, Apu from The Simpsons, you know what I mean? But there are Indian people in all different walks of life.” There are even ones who make vulnerability relatable, turning it into a tried and true formula for streaming supremacy. —Yasmin Duale

14. Belly f/ The Weeknd, "Might Not"

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Album: Up For Days

Producers: Ben Billions

Label: Roc Nation and XO Records

Released: 2015

When we refer to Toronto’s signature hip-hop style, there’s more to it than R&B vocals over eerie trap beats. There’s also the oddly urgent desperation in the lyrics, and “Might Not,” about a lecherous, drug-fueled evening that’s spiraling out of control, is a prime example. “The night’s too long/I took too much and I’ve gone too far/And I might not make it,” The Weekend sings on the hook, edging particularly dark (even by his standards) over energetic rhythms we typically hear backing choruses focused on trap-specific content (i.e. money, drugs, women). Belly, by contrast, takes things decidedly less seriously, literally laughing the situation off and spitting low-key genius punchlines like, “She say she don’t believe in God but her shoes Christian.” It’s one of the pioneering songs of the gauzy hip-hop and trap fusion that’s been attributed to the city, as few other tunes met in the middle in such a way before it.

The track is also a showcase of the XO nucleus in rare form. Belly, a stalwart of the Canadian hip-hop scene since the mid-2000s, has been The Weeknd’s secret weapon for years, with co-writing credits on some of the starboy’s biggest hits (including “Blinding Lights” and “Often”). He’s played a more important role in Abel’s oeuvre—which would prove instrumental in influencing the drug-dazed sway of 2010s pop music—than many realize. On “Might Not,” his highest entry on the Billboard Hot 100, we hear the pair’s chemistry at its finest, and a blueprint for the sound of many subsequent hits to emerge since. —Yasmin Duale

13. Choclair, "Let's Ride"

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Album: Ice Cold

Producer: Kardinal Offishall

Label: Virgin

Released: 1999

Canadian ears were reinvigorated following the success of “Northern Touch,” and now the individual all-stars from our national anthem had an opportunity to unleash hits of their own. Already a Juno winner in 1997, Choclair released debut album Ice Cold in 1999, and with it came the effortlessly smooth “Let’s Ride.” It opens with a one-two punch of Saukrates ad-libs followed by a piano lick courtesy of Kardinal so sticky it’ll live in your cranium for two decades and beyond.

If you were introduced to the Scarborough native from “Northern Touch,” you got a pretty good idea of what the bespectacled Chox is about: smooth with the ladies but also down to partake in something nerdier like Monday Night Raw with his pals. Comparatively speaking, “Let’s Ride” is a triumphant victory drive down downtown Toronto, and Choclair stars as the Joe Carter hero figure who just won the World Series. Chox oozes confidence throughout: he’s not only Carter, he’s all black like the Raiders, he’s outmaneuvering MacGyver, and he’s got flow like a BMW 850 down Lake Shore Boulevard. There are some epic Etobicoke shout outs as well.

As with other tunes from the era, having a perfect Little X/Director X music video to accompany “Let’s Ride” only helped his MuchMusic ascent. Choclair got another shot after “Northern Touch,” and instead of feeling the pressure, he made it look so easy. —Erik Leijon

12. Jelleestone, “Money Pt. 1”

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Album: Jelleestone Thirteen

Producer: Jelleestone, Jon “Rabbi” Levine

Label: Warner Bros. Records/Rex Entertainment Inc.

Released: 2001

The last summer of the pre-9/11 world was as an unforgettable vibe, in Canada at least, thanks to “Money Pt. 1,” Jelleestone’s feel-good, G-funk-laden banger that had a stranglehold on the Much Countdown (RIP). The song’s melodic, Adam Smith-approved hook—“Money can’t buy me happiness/But I’m happiest when I can buy what I want, anytime that I want”—was just the right amount of cheeky and infectious, at a juncture when Canadian rap was finally starting to get its due in the pop mainstream. It garnered Jelleestone some Juno nods (Best New Solo Artist, Best Rap Recording) and stateside success, including a spot on the Billboard Hot 100 and a U.S. album deal with Warner Bros. “It thrust me into a real pop realm—a realm where Canadian rap artists have not been,” he told Now Magazine at the time.

Due to untimely circumstances—including a gun charge that prevented him from touring and a Warner restructuring that killed the promotional cycle for his debut album Thirteen—Jellee never got to realize his full potential. Still, he helped a generation of kids see the potential in themselves. The rapper gave youth in his hometown of Rexdale, and under-resourced Toronto communities like it, someone to look up to. He also served as a major inspiration to one Noah “40” Shebib—a then-unknown producer he recruited to work on his sophomore LP, who would later become Drake’s right-hand man—and even Drizzy himself. After all, The Boy interpolates the hook from “Money Pt. 1” at the end of 2016’s nostalgia-rife “Weston Road Flows.” It’s entirely possible Jellee helped turn a young Aubrey on to hip-hop with pop sensibilities. And, well, we all know the rest of that story. —Alex Nino Gheciu

11. Michie Mee and L.A. Luv, "Jamaican Funk—Canadian Style"

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Album: Jamaican Funk—Canadian Style

Producer: King Lou, L.A. Luv, Maximum 60, Capital Q, Michie Mee

Label: First Priority Music/Atlantic Records

Released: 1991

Queen Michie Mee is an unparalleled Canadian rap pioneer as the first to sign a major American record deal. The Jamaica-born, Toronto-raised MC caught the ears of Boogie Down Productions and made appearances on two formative ’80s rap compilations: 1987 Canadian showcase Break’n Out and 1988’s The First Priority Music Family: Basement Flavor.

After amassing some early attention, Mee and Luv began the next decade with the dancehall/rap hybrid “Jamaican Funk—Canadian Style,” a more memorable remix of the initial “Jamaican Funk,” and the rest was history. On the track, Mee flexes her lyrical might, subverts male braggadocio and pays homage to her birth country. As with the album of the same name, Mee jumps between dancehall—and rapping in Jamaican patois—and more conventional North American rap with ease.

The song has hardly aged a day and it’s a reflection of Michie’s talents that a female-fronted, dancehall-influenced song would break into mainstream Canadian audiences in 1991. But how could “Jamaican Funk—Canadian Style” not leave such an indelible mark on the Canadian hip-hop scene? Michie’s “I’m Jamaican, taking charge and living large” confidence is infectious, and speaks to any Canadian immigrant who takes pride in where they’re from. —Erik Leijon


10. Team Rezofficial, “Lonely”

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Album: The World (And Everything in It)

Producer: Jay Mak

Label: Arbor Records Ltd.

Released: 2008

Back in the late aughts, Team Rezofficial dropped a track so undeniably cold it would bust open the door for Indigenous hip-hop in Canada. “Lonely,” off their sophomore album The World (And Everything in It), became the first song by an Indigenous act to not only crack the top ten on MuchMusic’s seminal RapCity countdown, but make it all the way to No. 1. The collective—composed of producers Jay Mak and Stomp, and MCs HellnBack, Drezus, and Tomislav, respectively repping the First Nations of Maskwacis, Alberta, Saskatoon, and Winnipeg—were impossible to ignore, giving nation-wide visibility to communities that justifiably felt overlooked and forgotten by the rest of the country.

Over a swinging, 6/8 beat that kinda sounds like a flip of “The Imperial March,” the group brings representation to the reservation with confidence and authority. “We grind on the streets, find us on them beats,” they chant collectively on the contagious hook, coming off like they’re screaming orders amid a heist of the Canadian hip-hop scene. The rappers then take turns spitting lyrically dextrous, charismatic bars about their relentless, take-all-comers hustle and desire to “come through for the people.” It’s not hard to imagine the impact “Lonely” had on First Nations kids seeing its music video in constant rotation on TV; it’s a braggadocious, empowering anthem that defiantly thumped its chest in the face of a system that aimed to silence and erase them, and beat the drum for a generation of Indigenous hip-hop acts, from A Tribe Called Red to Snotty Nose Rez Kids, who would follow in Team Rezofficial’s wake. —Alex Nino Gheciu

9. Haviah Mighty, “In Women Colour”

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Album: 13th Floor

Producer: Obuxum & Haviah Mighty

Label: Independent

Released: 2019

On “In Women Colour,” Haviah Mighty does what she does best—spit facts over a slick beat, letting her cutthroat lyrics shake the listener. Thematically, it’s rich, emotional, and brimming with passion. It was the perfect track to kick off her acclaimed album 13th Floor, which is an ode to the Black experience and the racism faced by the community. “In Women Colour” is a glaring tale of coming of age as a Black woman. It doesn’t pull any punches when it comes to detailing Mighty’s personal journey, as she details getting beat up by a group of boys while playing basketball in seventh grade. She’d eventually get the ultimate revenge: 13th Floor would go on to win the Polaris Music Prize, making her the first hip-hop artist and the first Black woman to win the award, which celebrates the best Canadian album of the year. And just a few years later, she’d become the first woman to ever win a rap album or EP of the year award at the Junos.

Her flow is effortless but fiery, commanding yet precise. The lyrics are deeply personal, but relatable, and signify just how much passion Mighty has for storytelling in music. It’s a track that proves Mighty has always been able to hold her own in the boys’ club that is hip-hop culture, while also paving the way for more women looking to make waves. —Natalie Harmsen

8. Rascalz f/ Barrington Levy and K-os, “Top of the World”

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Album: Global Warning

Producer: DJ Kemo

Label: ViK. Recordings

Released: 1999

Rascalz mix rap and dancehall for a collab with Barrington Levy and K-os that truly gives a global feel to old-school hip-hop. Everyone has a moment to shine on the song, with Rascalz shouting out their West Coast roots and K-os unleashing a verse that’s so sharp but sounds completely effortless (who else could rap about spreading love from Kelowna to Kalamazoo?).

Levy’s chorus cleverly makes use of a sample of R. Dean Taylor’s “Indiana Wants Me” in a way that feels equal parts nostalgic and mellow. It’s playfully experimental and expansive, which is likely why it was so popular when it was released and made it to No. 1 on the Much Countdown.

The lyrics pay homage to the foundation of the group and their respect for the four elements of hip-hop, while still expressing their love for creating a worldwide vibe. The track cements Rascalz’s place as one of the groups at the helm of Canadian hip-hop, but also speaks to what has influenced them beyond the borders of the Great White North. Mixing the sample of a Canadian’ 70s rock song with a dancehall-inspired beat isn’t just creative—it’s a track that plays not only with genre but with the idea that hip-hop music can be a cultural mosaic. —Natalie Harmsen

7. Baby Blue Soundcrew, “Money Jane”

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Album: Private Party Collectors Edition

Producer: Kardinal Offishall

Label: Universal Music Canada

Released: 2000

This is the kind of song that every Canadian knows word for word, even if they think they don’t. And though we’re all very familiar with the track’s featured voices, this is widely considered a breakout for each of them. The sonic synergy between Kardinal Offishall, Jully Black, and Sean Paul worked in a way that very few things do. Their tones and cadences are so complimentary that it feels like we’re listening in on a conversation between friends, with Black on the chorus and Offishall trading verses with Paul.

This not only laid the foundation for each of their career trajectories, it also helped shape what would later morph into ‘the Toronto sound.’ At the time, there was value in mimicking American sounds—sounding distinctly Canadian wasn’t necessarily the ideal for emerging rap artists looking to crossover. But this track forges its own sound and that’s its strength and legacy. The story goes that the song was originally Kardinal’s, and Kid Kut from Baby Blue Soundcrew suggested he add Sean Paul. The rest is history. In 2000, hip-hop and dancehall weren’t necessarily considered key elements of Canadiana but this collab between the then-emerging, now-iconic trio of Paul, Black, and Offishal could easily be a Canadian Heritage Minute (if you know, you know). —Sumiko Wilson

6. Drake, "Back to Back"

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Album: N/A

Producers: Daxz, 40, Drake, Nav

Label: Cash Money, Young Money, Republic

Released: 2015

Songs born out of beefs are always momentous, but when Drake dropped “Back To Back” mid-Meek Mill scuffle, it felt seismic. This is a song that feels frozen in time: It dropped the weekend of OVO Fest, while Meek Mill was still dating Drake’s long-rumoured fling Nicki Minaj and the name ‘Quentin Miller’ was on everybody’s tongues (and feeds). The track was released after Meek accused Drake of using Miller a ghostwriter, which didn’t pan out to be the burn that he thought it was, since Miller was credited as a contributor and therefore not a ghost at all.

Drake retaliated with not one, but two diss tracks: “Charged Up” and “Back To Back.” Both are etched in rap history, but looking back, “Back To Back” is the superior track because Drake is flexing all of his most star-making qualities. It’s refreshingly confrontational, highly quotable (“Is that a world tour or your girl’s tour?” should be etched into the side of a building erected in Drake’s honour), and as he’s made a habit of throughout his career, he unabashedly owns the things that people clown him for to diffuse and dominate conflicts. When this dropped, you couldn’t scroll through your feed without seeing “You gettin’ bodied by a singing nigga” at least a dozen times. This is a song where he’s comfortable in who he is and confident in what he does best. It’s also a timely reminder that Drake came of age in the battle rap era and has spent years sharpening his pen for this very moment. When he opened OVO Fest with this days later, it was the nail in the coffin. Drake and Meek have since reconciled and collaborated (see: “Goin’ Bad”) but this is a burn that Meek probably still winces at. —Sumiko Wilson

5. K-os, "Crabbuckit"

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Album: Joyful Rebellion

Producer: K-os

Label: EMI

Released: 2004

The first rap song to win the Juno Award for Single of the Year (in 2005) wasn’t K-os’ first rumination on the cutthroat Canadian music business after spending most of the ’90s jousting with the suits, but his universal message remains in the Canadian lyrical landscape: people in all walks of life have a tendency to compete with each other, typically to their own detriment.

K-os’ then-manager, NBA player John Salley, supposedly introduced his mentee to the concept of crab mentality. It was true then, when Kevin Brereton was part of a second wave of Canadian rappers fighting for respect from a continually hostile industry that still struggled to understand hip-hop, and it’s true now. It also helps that K-os wrapped his critique in an irresistibly groovy package, led by jazzy bass, stomping percussion, rhythmic handclaps, and a reappearing sax. It’s the sound of strutting down Yonge street with no fucks given.

The song was an undeniable breakthrough. K-os was a maverick in his time, sounding slightly out of lockstep with his peers, but it’s also his unique ear that gave him a mainstream radio rap hit in the middle of the indie rock revolution.

The words of “Crabbuckit” have had a lasting effect at home. In a rare interview with Billboard, even OVO founder Oliver El-Khatib couldn’t help but reference the song when talking about wanting to shine a light on his city. Today, nobody wants to be the crab pulling down his peers. —Erik Leijon

4. Kardinal Offishall, "Ol' Time Killin"

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Album: Quest for Fire: Firestarter, Vol. 1.

Producer: Mr. Attic

Label: MCA Records

Released: 2001

When your song and its music video net you fans like rap legends Pharrell, The Clipse, Zhane, and Pete Rock, you know you’re making a proverbial killin’. Or as Canadian soul queen Jully Black sings on the outro to “Ol’ Time Killin’”: “The emcee killa, killa killa.” She’s of course referring to marquee MC Kardinal Offishall, whose reliably slick and flagrant rhymes include: “Lick a shot, wave your flag, gunfinga in the air Headstone on your 12-inch says Mr. Kardinal and the Monolith was there.” Yes, Scarborough’s Monolith crew-featured rappers Wio-K and IRS (Korry Deez and Black Cat) also sound like musical “murderers,” as a refrain on the sample attested.

That beat comes from frequent Kardi cohort Mr. Attic and boasts a slinking xylophone like riff and prowling percussion. Their partnership was cemented with this underground hit which could’ve easily not happened—while on tour Kardi overheard the absorbing beat in his hotel room, coming from Attic’s room. The producer had planned to use it as an interlude but Kardi knew it could be so much more. His fittingly Jamaican-inflected vocals meshed with the instrumental’s reggae elements, and his footwork in the Little X-helmed music video, whose slow panning camera evokes the music’s mellow yet dangerous tones, all made Kardi’s lethal charisma official.

Lil Wayne recently named Kardi his favourite Canadian artist besides Drake, and for good reason. A rare breed, Kardi made music that was embraced by both underground and commercial hip-hop circles, not to mention the dancehall community—and “Ol’ Time Killin’” got all three realms equally fired up any time it was played. It’s easy to see why Drake insisted on being the one to drop the beat for this track at his All Canadian North Stars concert. If “Money Jane” is the song that invented the Toronto sound, “Ol’ Time Killin’” is the one that mastered it. —Kyle Mullin

3. Maestro, "Let Your Backbone Slide"

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Album: Symphony in Effect

Producer: Peter & Anthony Davis

Label: Attic/LMR

Released: 1989

Canada’s first hip-hop hit to chart on Billboard’s Top 40 holds up well over three decades later. That’s in part because of the catchy whir on the iconic track’s instrumental during the chorus, and the staccato percussion clinks beyond it, all courtesy of producers Peter and Anthony Davis. But be sure to give the Maestro his due, from his stacked lyrics (“every verb you heard I play snaps a vertebrae”) to his breathless flow. Together, the rapper and producers’ work helped “Let Your Backbone Slide” live up to its name, making enough Canadian and American listeners slide across the dance floor to prompt the Junos to nominate Fresh Wes for the Best Dance Recording award in 1990, which his former manager Farley Flex said in a CBC interview prompted them to create “the rap category the following year. You know, when we talk about impact, that’s the real deal.” (Fresh Wes would go on to win the very first Juno for Best Rap Recording in 1991.) Indeed, when he rhymed on the song that “My lyrics are awesome, tunin’ from human, bloomin’ a blossom/Blowing away blockades and barricades,” Maestro seemed to also be making a self-fulfilling prophesy about the barriers he’d break in Canada’s then-nascent, but now-dominant, rap industry. —Kyle Mullin

2. Rascalz f/ Checkmate, Choclair, Kardinal Offishall, and Thrust, "Northern Touch"

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Album: N/A

Producer: DJ Kemo

Label: Figure IV/ViK./BMG

Released: 1998

Like a Canadian answer to the Wu-Tang Clan, our nation’s top MCs in the ’90s gathered for a rawly cypher-esque single that put the Great White North on the map. Not merely in Canada, but also the highly coveted (and before then elusive) U.S., Rascalz’s “Northern Touch” cracked the top ten in numerous markets. The Vancouver rap crew’s members certainly shine on the song, from Red1 and Misfit’s mind meld-like interlocking bars to DJ Kemo’s coiled python sample of “Everything Good to You (Ain’t Always Good for You)” by B.T. Express (which was also, by chance, used the same year on DMX’s early cut “Get At Me Dog”). But aside from Rascalz, fellow Vancity rapper Checkmate along with would-be Toronto heavyweights Thrust, Choclair and, of course, the ever-charismatic Kardinal Offishall on the chorus, also bring an abundance of bars to bear.

The rappers involved overcame the era’s technological limits—no email, much less cloud sharing or Zoom—by sending a two-inch thick tape of the demo to their Toronto cohorts to record on, somehow maintaining an adhesive-esque catchiness and cohesion regardless. Aside from recording a track that allowed the members to play off each other’s complimenting styles, the song also connected Canada’s fragmented and largely indie West Coast rap communities with the more established Toronto. Not that Toronto was miles ahead by any means, because Canadian hip-hop was largely dismissed until “Northern Touch” broke through and proved our underrated nation had swaths of rappers who could hold their own against just about any more publicized American counterpart. We shouldn’t take for granted Drake and his ilk’s current prominence on the global stage, because Rascalz and co. made going international possible. —Kyle Mullin

1. Drake, “Know Yourself”

View this video on YouTube

Album: If You’re Reading This It’s Too Late

Producers: Boi-1da, Vinylz, Syk Sense

Label: OVO Sound/Young Money/Cash Money/Republic

Released: 2015

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


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