10 Canadian Rappers Not to Miss at Rolling Loud Toronto

It wouldn't be a first-ever Rolling Loud in Canada without a few prominent Canadians in the lineup, and the inaugural Rolling Loud Toronto is not lacking.

Toronto Haviah Mighty will be performing at Rolling Loud
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Toronto Haviah Mighty will be performing at Rolling Loud

Toronto Haviah Mighty will be performing at Rolling Loud

It wouldn’t be a first-ever Rolling Loud in Canada without a few prominent Canadians in the lineup, and the inaugural Rolling Loud Toronto is not lacking in rappers representing the red and white.

The three-day festival has some of the biggest names in the country set to perform, including Nav, who’s dropping an album today, Roy Woods and more. It’s also going to be a platform for up-and-coming acts to prove they can stand alongside a number of big-name imports from the United States and England.

Beyond Canadians, it’s also going to be one of the deepest rap lineups ever assembled in Canada, including headliners Dave, Future and Wizkid, plus Lil Uzi Vert, Roddy Ricch, Skepta, and Lil Yachty. And that’s not including the likelihood of special guests and other unannounced surprises.

For those heading to the site, it’s looking like Migos and Belly are no longer scheduled to perform. You can check out the 3-day lineup here:

If you happen to be checking the first Rolling Loud to hit Canada this Sept 9-11 at Ontario Place, here are 10 Canadian artists to check out.

Roy Woods

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Performance: Friday, 6:20 p.m., Uber Stage

Brampton-born OVO Sound signee Roy Woods was supposed to drop his latest album Mixed Emotions on Aug. 5, but it didn’t happen. The artist said on Twitter he’s adding something special to it, hence the delay, but one can imagine the new release will figure prominently during his Rolling Loud set. While we wait for the new album, his latest single is the DJ Charlie B-produced “Bad Bad,” which takes Woods back to his Guyanese roots. He also dropped “Insecure” earlier this year.

Night Lovell

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Performance: Friday, 8 p.m., Moose Knuckles Stage

The Dark Knight of Canadian rap. The Ottawa artist isn’t afraid to dabble in murky and brooding sounds, and in the past has collaborated with likeminded acts like $uicideboy$ and YouTuber Corpse. He’s got an uncanny ability to bring a dark atmosphere to party rap, and has the millions of streams to back it up. In July, Night Lovell teamed up with American rapper $not on the single “Ms. Porter.”

Smiley

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Performance: Saturday, 4:50 p.m., Uber Stage

Sporting a unique flow and hailing from Toronto’s Pelham Park, Smiley has been a highly touted young gun for OVO since his break out 2021 single “Over The Top” with label boss Drake. He quickly followed up the successful single with album Buy or Bye 2, and then he dropped a deluxe version of the release a few months later. His unmistakable style got the attention of Drake back in 2017, and since then he’s relocated to Los Angeles and dedicated himself to his craft. His “Rush Hour Freestyle” from June has crossed 500,000 streams on Spotify and he dropped “Gangsta Gentleman Remix” with fellow Toronto rapper TVGucci in August.

Burna Bandz

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Performance: Saturday with Why G, Talluptwin, 8:05 p.m., Moose Knuckles Stage

Jane and Finch’s Burna Bandz took part in one of the great independent success stories in modern Canadian rap with “Late Nights” with the late Houdini, and as the 2018 continues to gain in lore, he’s ever ready to respond to his naysayers, as he does on new single “Shade,” where he says: “What’s with all the hate, what’s with all the shade?” He’ll probably get even more attention when his next mixtape drops, due imminently according to a recent interview with MuchMusic.

Pressa

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Performance: Saturday, 5:50 p.m., Uber Stage

It took moving to Los Angeles to have his mainstream breakthrough in his home country, where we received four Juno nominations in 2022, but no matter where he ends up, Pressa is never far from the Driftwood neighbourhood of Toronto where he was raised. After dropping Gardiner Expressway in 2020 (with a deluxe version with Swae Lee and Coi Leray in 2021), Pressa came back in a big way the release of confrontational new single “Blame Me” in August.

Frvrfriday

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Performance: Saturday, 5:55 p.m., Moose Knuckles Stage

The Edmonton-born rapper is rising fast with every new single since his 2020 collaboration “Window Shopping” with Lil Baby. After two R&B/rap hybrid-style tracks in “Priceless” and “Time for You” a year ago, Frvrfriday came back swinging at the end of 2021 with the punchier “Time & Its Order.” And he hasn’t really stopped since then, as he turned up the vocal effects on “How Would You Feel” before coming back with hook-laden “Flylikedis.” Whether he’s more in the R&B side or the rap one, he’s got an undeniable ear for sticky melodies.

Haviah Mighty

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Performance: Saturday, 4:50 p.m., Bet 99 Stage

In 2019, the Brampton native became the first rapper to win the Polaris Music Prize for Best Canadian Album for the 13th Floor, and more recently in 2021 dropped acclaimed mixtape Stock Exchange. The accolades don’t stop there, as she also took home Best Rap Album honours at the 2022 Juno Awards. She’s not resting on her laurels, as she said she’s got “another one” coming on Sept. 23. 

Nav

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Performance: Sunday, 8:20 p.m., Uber Stage

What more can be said about Nav at this point? He just dropped the star-studded Demons Protected by Angels this morning with Lil Baby, Travis Scott, Lil Durk, Gunna, Lil Uzi Vert, Bryson Tiller and more. Back in July, he sat down with Complex for an extensive interview that detailed the process of the new album and how’s grown in and out of the studio. Can we expect guest stars and surprises during his triumphant Toronto return?

Skiifall

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Performance: Sunday, 7:25 p.m., Moose Knuckles Stage

The fast-rising Montrealer just turned 21, but he’s already accomplished quite a bit before hitting legal drinking age in the States. It all started with fiery first single “Ting Tun Up,” which found success in England, where Knucks eventually jumped on the track for a remix. Skiifall has since signed to XL Recordings, where he dropped “Break of Dawn” with BadBadNotGood and the solo track “Bloodcarrt Business.” He’s also had the opportunity to cut his teeth live touring with BadBadNotGood and Denzel Curry. Back in March, he posted that he’s working with Charlotte Cardin on a follow-up to Woiiyoie Tapes Vol. 1

SLM

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Performance: Sunday, 3:50 p.m., Bet 99 Stage

Montreal rapper SLM (pronounced “Slim”) burst onto the local scene in 2020 with debut album SLM: The Complete Flex Season, which showed that even though she was a fresh face in Montreal rap, she was someone to watch going forward. Her live shows in her hometown have been electric, with backing dancers to go along with her fast-paced style. She dropped slower, smoother 4-song EP Real Talk Radio in 2021 to show she’s got different facets to her music. She also appeared on Montreality’s first English Montreal rap cypher in late 2021.

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