20 songs that tell the story of Canadian hip-hop

How does one define Canadian hip-hop? The genre has evolved so much over the decades that we decided to tell its story through song. 

From the very first hip-hop record made in Canada to emerging artists pushing the modern boundaries of the genre, there's a lot to contend with. This list of 20 songs represents pivotal shifts and crucial moments in hip-hop across the country. 

CBC Music consulted 10 hip-hop experts — including radio hosts and rappers, DJs and A&Rs — who shared the songs they think define the story of Canadian hip-hop. Some tracks are instantly recognizable hits, while others highlight artists who may not have the ubiquity of a Drake or a Michie Mee but who have still left an indelible mark on the genre. 

You'll notice a lot of men on this list, which reflects the lack of support for women MCs in the earlier days of Canadian hip-hop, when they weren't getting platformed or promoted in the same ways as their male counterparts. Things are much better now, thanks to the groundwork laid by trailblazing women in the genre. 

It's impossible to tell the full story of hip-hop in just 20 songs, and we received many more suggestions than this list could accommodate — so we created a playlist including all the experts' picks (and some extra gems) for deeper listening. You can find it below.

Let us know which songs you think are the definitive Canadian hip-hop records on Instagram @cbc_music or on Twitter @cbcmusic. 

'Ladies Delight,' Mr. Q (1979)

The first rap song created in Canada came out of a basement studio in Toronto's Little Jamaica neighbourhood. "Ladies Delight" was Mr. Q's rollicking answer to Sugar Hill and the Gang's "Rapper's Delight." But for decades, it wasn't included in early Canadian hip-hop history until its story resurfaced in 2021, thanks in part to an in-depth profile on Mr. Q published by Hazlitt. For many rap fans who weren't around in 1979, their first introduction to "Ladies Delight" was on a 2006 compilation record called Big Apple Rappin': The Early Days Of Hip-Hop Culture in New York City 1979-1982, which led many people to assume it was an American-made track. But Mr. Q, also known as Jay McGee, cut the record at Monica's Productions, a recording studio under a cosmetics store in Little Jamaica. 

"Jay was that guy, he could rap, sing, he could kill anything you asked him to do," said David "Clik" Cox, a music manager, former A&R and member of Juno-nominated rap group the Maximum Definitive. "'Ladies Delight' was really birthed out of the Jamaican culture in Toronto, in the sense that Monica's would do real reggae style dubplates and they would take records that were already popular and remix them in the dubplate style. The reason it never really came to be known as a Canadian record is because they just took the records and drove to Buffalo and sold them into the American market." 

'Let Your Backbone Slide,' Maestro Fresh Wes (1989)

"Let Your Backbone Slide" was the debut single from an artist who would become known as the godfather of Canadian hip-hop. Maestro Fresh Wes paired slick rhymes with funky rhythms, record scratches and inspired sampling (James Brown, Public Enemy, Doug E. Fresh) to create a ubiquitous hit. It held the title as best-selling Canadian hip-hop single for 19 years. The album it appeared on won the first ever Juno Award for rap recording of the year in 1991. 

"Wes is my older brother, so I had a front seat to the whole making of what he did," said award-winning DJ and radio host Mel Boogie. "My kids don't believe it, but there was a time when Maestro went to sign autographs at HMV and they had to shut down the mall, because there were that many people there. This was the first rap song many people heard on mainstream Canadian radio. For Wes to have the success he did at that time astounds me because he had nothing. College radio was the only support, he actually had to go to clubs and physically give out a record to the DJ to play, stuff that we kind of take for granted nowadays. Lyrically, it could go toe to toe with a Big Daddy Kane, or Kool G Rap or Rakim, like those lyrical kinds of MCs. I think that's what made it stand out, his flow, and the catchiness."

"There was no rap category before Wes came along," she added. "They had to create that to recognize the fact that rap as a genre was growing in Canada and we had talent here that deserved the same recognition and accolades that Bryan Adams and the Tragically Hip and Rush had been getting."

'So Listen,' MCJ and Cool G (1990)

Both MCJ and Cool G are originally from Halifax, but the duo formed in Montreal after they both had moved there separately. They knew each other from when they used to cipher back in Halifax, and were early adopters of the R&B and hip-hop fusion that groups like Bell Biv Devoe popularized. "'So Listen' was their hit single," said Duke Eatmon, a musician, CBC Montreal radio columnist and promoter. "They became local celebrities overnight after the video went up on MuchMusic and Musique Plus. This moment happened like 10 years after hip-hop had already arrived in Montreal, but they marked Montreal's commercial entry into the Canadian hip-hop industry at large. It also marked the beginning of that new fusion thing, preceding Bell Biv Devoe by about a year. MCJ and Cool G also toured the world with MC Hammer, Public Enemy and Vanilla Ice." 

'My Definition of a Boombastic Jazz Style,' Dream Warriors (1990)

"My Definition" was an early single off the Toronto duo Dream Warriors' 1991 debut album, And Now, the Legacy Begins. A prophetic title, considering Dream Warriors' singularity and devotion to their sound would go on to shape the future of hip-hop in Canada. King Lou and Capital Q heard Quincy Jones's "Soul Bossa Nova" while in a bar and knew immediately they wanted to try rapping over the flute. Nothing like it had been done before, and their inspired sample experimentation paid off. The song was a hit in Canada and especially in the U.K., where it reached the Top 20 and got featured in BBC's Top of the Pops. With the release of their debut album, Dream Warriors situated themselves as players in the jazz-rap movement of the '90s.

'Jamaican Funk—Canadian Style,' Michie Mee (1991)

In 1988, off the strength of "Elements of Style," Michie Mee became the first Canadian MC to sign a deal with an American major label, Atlantic Records. She is a pioneer of Canadian hip-hop, and one of few women in the game who has risen to legend status. "Jamaican Funk" is a rambunctious ode to her culture and the roots of the genre. 

"When I saw the 'Jamaican Funk' video for the first time, I remember my eyes were just glued to the screen, I didn't blink, I didn't want to miss a thing," said Mel Boogie. "It was like the movie Dancehall Queen, but a hip-hop video. Michie did a lot and I still don't think that she's gotten a lot of the recognition that she deserves. There weren't any blueprints. Artists coming up now have way more resources, technology has made that easier. It kind of makes me feel happy and proud that she was able to do as much as she did with as little as she had."

'Father Time,' Saukrates (1995)

Saukrates is part of the '90s wave of Toronto rappers that proved MCs north of the border could go toe to toe with their contemporaries down south. He's a lyrical beast, expert rapper, producer and singer, completely devoted to his craft. He's worked with everyone from Method Man to Common, Kardinal to Drake. 

"This is one of the craziest beats," said Junia-T. "Saukrates is in rare form as a producer-MC, and for me, also being a producer-MC this track was a huge inspiration to see that it was possible to have a pen that was that crazy and also make beats that crazy at the same time. This was also a song that made Toronto heard outside of the city, early in the game. He's being braggadocious but saying some real poignant things about being a confident person in the face of people expecting you not to have confidence for so many reasons, whether it's being a Black man, where we're from, or even just being a Canadian artist in the industry, there's definitely undertones of that." 

'Autonomy,' Tara Chase (1997)

Tara Chase fell in love with hip-hop growing up in Montreal, listening to her dad's rap records. She ultimately moved to Toronto for work, where she released "Autonomy": a track produced by Saukrates that appeared on Rap Essentials Volume 2 and became Chase's first commercial success. 

"Tara Chase is a god MC from that time," said Junia-T. "I remember this song stopping me in my tracks. The piano is so crazy and her flow is so buttery. She just floats on the whole song. She's an ill MC, period. It wasn't about her being a girl, she just bodied the joint." 

'La Force De Comprendre,' Dubmatique feat. Dessy Di Lauro (1997)

When DJ Choice, a pioneer of the Quebec hip-hop scene, got together with OTMC and Disoul, two Montreal transplants from Senegal, a new wave of French rap hit the country. Dubmatique's debut album, La force de comprendre, went platinum, selling 125,000 copies, and garnered them wide acclaim, including Juno and ADISQ award nominations. 

"This was the first really big explosion of French hip-hop in Montreal," said Duke Eatmon. "They released their debut album, and it sold over 100,000 copies in Quebec alone, and did well in other French-speaking countries and they ended up touring France and Morocco. They brought in a whole new style, because they weren't rapping in Québécois, but more so a Parisian/African style of French. And of course, with the great vocals of Dessy Di Lauro, they were just on that whole Fugees thing."

'Northern Touch,' Rascalz feat. Checkmate, Choclair, Kardinal Offishall and Thrust (1998)

"Northern Touch" was a historic collaboration between the hip-hop scenes in both Vancouver and Toronto. Rascalz (Red 1, Misfit and DJ Kemo) and Checkmate repped Vancouver while Choclair, Kardinal and Thrust repped Toronto on the electric banger that put Canadian hip-hop back on the mainstream industry radar. Things had waned a bit since Maestro Fresh Wes's "Let Your Backbone Slide" swept the nation, and "Northern Touch" provided an anthem about the resilient nature of the artists who grinded so hip-hop could maintain its foothold in the Canadian music landscape. 

"When you think of Canadian hip-hop, this song is on everyone's list," said Mel Boogie. "I don't care who you are, whether you're old or young. It was one of the first big collabo tracks, we hadn't had any that were this successful before. It was like a joining of Canada on one track." 

'Let's Ride,' Choclair (1999)

"Let's Ride" was Choclair's debut single, produced by Kardinal Offishall and featuring ad-libs by Saukrates (the trio came up together in the Toronto scene and were all frequent collaborators). The track was an explosive introduction to Choclair, where he laid insightful bars and gave you something to groove to at the same time.

"I have a really personal memory associated with this song, because earlier this year, I was a part of the 50th anniversary of hip-hop performance at the Juno Awards," said Haviah Mighty. "Choclair performed 'Let's Ride' with Kardinal, who produced the record. I was onstage, [and] having the opportunity to kind of just vibe with them is still an unfathomable moment of my life. And that's where I really realized the intricacy of the flow, in the live rendition. One thing that I love about Choclair, he really has bars and just a really dope cadence. Throughout his verses he switches things up, you don't really know where he's going. It's very unpredictable." 

'Ol' Time Killin',' Kardinal Offishall (2001)

The immediate iconography you see in the "Ol' Time Killin'" video is a DJ sound system like one you'd find in Kingston, Jamaica, with the colours of the Rastafarian flag. The high-energy and boastful track, featuring IRS and Jully Black singing the hook, pays direct homage to the sound-clash culture that birthed hip-hop. Kardinal Offishall is known for repping the T Dot, but he also wears his Jamaican pride just as boldly. 

"When we talk about the roots of rap music, the story goes, Jamaican DJ Kool Herc moved to the Bronx, and imported the toasting and MCing over records they were doing in dancehall culture," said award-winning author and hip-hop journalist Dalton Higgins. "He and his sister, Cindy Campbell, threw what became the first rap gathering in 1973 and that laid the foundation for this new genre to emerge.

"The video for 'Ol' Time Killin'' was shot by Director X, who was still going by Little X at the time. And the imagery recalls the reggae dance halls of yesteryear. Lyrically, it really captures the essence of rap music and hip-hop culture, the hypothetical desire to 'kill the other person on the mic' and to prove that you're the baddest rapper in town. Kardinal does that in spades." 

'Fuel Injected,' Swollen Members, Moka Only, Mad Child (2001)

This multi-award-winning Vancouver group has released nine albums since its first, Balance, in 1999. As of that debut, Swollen Members have gone gold, then platinum, taken home four Junos for rap recording of the year and remained a mainstay in the Canadian hip-hop conversation. MadChild and Prevail make up the core of the group, joined occasionally by Moka Only and a rotating cast of characters over the years. 

"This is just one of those recognizable joints, for me," said Haviah Mighty. "I listened to it a lot growing up and I love the chord progression and the simple melody. Swollen Members were a large part of West Coast hip-hop and even growing up in Toronto and Brampton, I was exposed to a lot of their music. I discovered so much, including them, just by listening to deep cuts on my cousin's Walkman, or watching MuchMusic when I was young. The seeds of all that definitely influenced me, even unknowingly, when I started rapping myself, at age 12." 

'Crabbuckit,' k-os (2004)

The first single off k-os's 2004 album, Joyful Rebellion, "Crabbuckit" tells a story as old as time. It is said that crabs stuck in a bucket will pull down any crab that tries to escape, and in "Crabbuckit" k-os applied that to human beings and the way they tear down others who rise beyond their circumstances. As heavy as the subject matter is, the drums, handclaps, jazzy saxophone and k-os's inimitable delivery make this an enduringly catchy hit. 

"This is one of the best songs ever made: from the production, to the theme, to the music video, to the messaging, to how long that messaging has been relevant, and how long it will continue to be relevant, everything," said Haviah Mighty. "'Crabbuckit' solidifies k-os as one of the most talented and one of the most impactful artists in the Canadian landscape ever. And another thing I love about this song is it's hip-hop, but it's like it doesn't have to be, it can live outside of the hip-hop world." 

'Best I Ever Had,' Drake (2009)

Drake is a bonafide superstar, and his rise over the past 14 years has been formidable. The roots of that incoming superstardom were already visible in the rapper's early days, and his 2009 So Far Gone EP, as a recent Young Money signee, put him on the map — and he hasn't fallen off for a second since. "Best I Ever Had" hit No. 2 on the Billboard Top 100 at a time when rap wasn't charting as universally as it does now. 

"This single showcases Drake at his finest, where he's equal parts vocalizing and rapping," said Dalton Higgins. "It's not an easy thing to do and he does quite well. The first time I heard this track, I knew that he was going to be a thing, that he had a certain je ne sais quoi. I was in New York and it was playing all the time on their commercial radio stations, this was at a time when no Canadian rap acts, other than Kardinal, were getting regular rotation like this. It was a game-changer. Everywhere you went, from Brooklyn to Harlem, any borough, you were hearing this song 24/7. It's the track that broke him out to the world, and the rest is history." 

'R.E.D.,' Halluci Nation feat. Yasiin Bey, Narcy and Black Bear (2016)

Halluci Nation's electric powwow lends itself so well to hip-hop, and the group has collaborated with many hip-hop artists over the years: Boogie the Beat, Saul Williams and Shad, to name a few. On "R.E.D." Halluci Nation is joined by Yasiin Bey (f.k.a. Mos Def), from Brooklyn, and Narcy, a stalwart of Montreal's rap scene, originally from Iraq. Both their verses are teeming with energy, and the song feels like a shot of adrenaline. 

"When I think of that song, I think of Indigenous resistance, but also of global solidarity," said Shad. "You've got Narcy, you got Yasiin Bey, you got Halluci Nation. I don't know if I'd ever heard that kind of global resistance music, so it stands out to me as a contribution to hip-hop, for that reason."

'Gang,' Tre Mission (2016)

Tre Mission makes grime music, an offshoot of jungle and U.K. garage that takes rapping to astronomically faster speeds. Mission is known as one of the first North American grime artists, as the genre has its roots in early 2000s East London. His 2014 album, Stigmata, includes some of the heavyweights of the genre — Wiley, JME and Skepta — as well as fellow Canadians k-os, Andreena and Saukrates. 

"He's the first one to do it," said Junia-T. "He's top-ranking over there [in the U.K.]. I've been a fan of Tre Mission for a long time. When he got signed to Big Dada Sound, I was like, 'Who's this Canadian guy on Roots Manuva's label? He must be crazy ill.' He's a highly skilled lyricist because he's got that grime timing. That's not regular rapping, that's like, almost triple-time. To be able to rap that fast, but also write an idea with syllables and words, to fill up all that and still say something really brilliant, is like a next-level skill." 

'Super Nova Scotian,' Classified feat. Pat Stay, Skratch Bastid, JRDN, Quake Matthews, Knuckles, Bubbles (2019)

Classified released his first album, Time's Up, Kid, in 1995 when he was 18. The Enfield, N.S. native has shared stages with Ludacris, Busta Rhymes, Nas and the Black Eyed peas, but he's always stayed true to home. On "Super Nova Scotian," he enlists fellow East Coasters Pat Stay, DJ Scratch Bastid, JRDN, Quake Matthews, Knuckles and Bubbles for an ode to their home province that highlights all their different styles. 

"Classified is a very significant figure in Canadian hip-hop, he's prolific. He's got 16 albums out and he's developed so much as a producer and a songwriter, it's something pretty unique," said Shad. "You got Pat Stay on this record, too. Rest in peace, Pat Stay, one of the greatest battle rappers ever. I also wanted to pick a song with a DJ on it because DJing is one of the elements of hip-hop. It's actually the foundation of hip-hop and Canada actually has a great history when it comes to scratch DJing and party-rocking DJing, like we have some of the best in the world." 

'No Shade,' Myst Milano (2021)

Myst Milano defies the rigid conventions of genre by rapping over ballroom and house beats. Their 2021 album, Shapeshyfter, is full of eclectic, left-field production, but there's no denying Milano is a killer MC. Electronic music genres like house and techno are rooted in Black culture, just as hip-hop is, and there's been a concerted push recently to reclaim that history. Milano is at the forefront of a groundbreaking new sound in Canadian hip-hop. 

"This came out a couple of years ago, but it feels like it's still building momentum," said Cadence Weapon. "It's a new classic to me. Myst is such a unique artist, the kind of artist that I always hoped would come after me. This was always my vision of like, 'I hope that some people start rapping over electronic music and coming with different perspectives and different vibes.' I always was so lonely when I first started out because even within my underground rap world, I was the only person who was really rapping over electronic beats. Then I see an artist like Myst Milano or Cartel Madras, I get really excited. And I'm like, yes, the freaky shit's coming." 

'Elle est partie,' Sarahmée (2021)

With Sarahmée's tight lyrical delivery and no-nonsense demeanour, the Senegal-born, Montreal-raised artist has carved a nice space for herself in the rap Québécois world. She's not afraid to stand behind her politics, rapping about police brutality and systemic racism, and spotlights the plights and tenacity of marginalized women. Sarahmée has developed a definitive voice over her 15-year career, and "Elle est partie," with its themes of women reclaiming their place, agency and autonomy, encapsulates it flawlessly. 

"Most female rappers here are underground," said Nantali Indongo, CBC Montreal radio producer, host and member of Nomadic Massive. "Sarahmée is one of the very, very few who are super mainstream, and she's been at it for a while. She's also probably the first Black woman, after J-Kyll of Muzion, to get this level of visibility, attention and as a solo artist. When I saw the video for 'Elle est partie,' I was like, 'OK, girlfriend, you have arrived.' She's a Quebec celeb and therefore she should be a Canadian celeb. And it's dope because aside from Jully Black, I don't know many other dark-skinned Black women, at that level, you know, in music in Canada."

'Atlantic,' Haviah Mighty (2021)

Along with Phoenix Pagliacci, Lex Leosis and Keysha Freshh, Haviah Mighty was part of the feminist hip-hop group the Sorority, a groundbreaking act that came together in 2016 after an all-women cipher on International Women's Day. However shortlived the moment, it was a catalyst. After the group disbanded in 2019, Mighty continued to make major leaps and bounds for women in Canadian hip-hop: in 2022, she became the first woman to win a Juno Award in the rap category since 1991, when the genre was first recognized by the awards show. She won rap album/EP of the year for Stock Exchange, a record that showcases her lyrical prowess, adaptability and versatility. On "Atlantic," one of the standout tracks, she dives into the aftereffects of the transatlantic slave trade on our modern world. 

The Block is counting down to hip-hop's anniversary by airing 50 stories over 50 days that focus on significant artists, events and moments in hip-hop history. The 50 stories will air nationwide each night on The Block on CBC Music until Aug. 11 to coincide with The Block Party.