With many music festivals making their return to Canada in 2022, after the COVID-19 pandemic shut them down for two years, it’s no surprise that Drake is bringing back his OVO Festival to Toronto. Now in its tenth iteration, Drake put a twist on his annual homecoming party to celebrate the milestone and instead made it a tour he’s planning to take on the road, replacing his usual Caribana weekend event with what he’s called October World Weekend. In a similar format to what OVO Fest was in the past, October World Weekend consists of several concerts taking place during Toronto’s Caribana festival. The event includes Chris Brown & Lil Baby performing at Budweiser Stage on July 29th, and the main attraction being a Young Money Reunion show featuring Drake, Lil Wayne and Nicki Minaj on August 1st. To kick things off though, there would be an all-star lineup of Canadian artists performing at Drake’s newly built nightclub, History, effectively being a tribute to classic Canadian Hip-Hop and RnB.

Initially dubbed the All Canadian NorthStars, the lineup of artists was just announced earlier this week, and the exceptionally priced $20 tickets were sold out within a few hours. The lineup consisted of iconic artists who pushed through mainstream media’s discrimination against the culture and artform in the ’80s, ’90s and ’00s to pave the way for artists like Drake, including Toronto emcees Maestro Fresh Wes, Kardinal Offishall, k-os, Choclair and Saukrates, plus Vancouver’s own Rascalz, and Detroit natives with a close Canada connection, Frank-n-Dank. It also included RnB stars Jully Black, Glenn Lewis, In Essence, Keshia Chanté and Shawn Desman, plus other surprise guests. This show would be an incredible, rare opportunity to see all these Canadian icons in the same place, at the same time, celebrating the legacy and impact they’ve collectively made on Canadian music.

With this being my first time going to History, I decided to show up a little early to check the place out. Everything about this venue speaks classiness, as all the fixtures, lighting and equipment are brand new, the club has its own metal detectors at the doors, security and hosts greeting you at the doors wear suits, and the urinals have dividers between them. Everything has a fresh, sleek design to it, and even though it’s located far out east from the downtown core, it’s bound to quickly become a favourite for Toronto concert venues.

The show was scheduled to start at 10pm, and it began with DJ Agile continuing to spin early 2000s Hip-Hop as he had been doing all night. About half an hour in, Drake himself came out to open the night up with a speech about how he grew up being a fan of all the artists we were about to see perform, and how these were all major influences on his career as he came up in the Toronto music scene. He would shoutout several key pieces of Toronto’s Hip-Hop history, from record stores to promoters to radio stations, and would introduce the first artist of the night, Maestro Fresh Wes.

Seeming to start this journey chronologically, Maestro was one of the first emcees to put Toronto Hip-Hop on the map back in the ’80s, and he kicked things off with his 1989 hit “Drop The Needle.” The crowd was hyped from the beginning, as they sang along to “Stick To Your Vision,” and Maestro proudly proclaimed how he was still able to jump around on stage in his mid-50s, getting the crowd to jump with him to “Conductin’ Thangs.” With a B-boy getting down on stage next to him as he performed, Maestro would close out his time on stage with the all-time classic, “Let Your Backbone Slide.” To simplify what Maestro means to us: this is as close as we can get to a Canadian equivalent to Big Daddy Kane (my opinion).

Things would move along quickly, as next to hit the stage were Frank-n-Dank, performing the J Dilla track “Pause.” Although the duo is from Detroit, they do have a close connection to the early Canadian Hip-Hop scene, as they’d next perform a track produced by Saukrates, “Nice 2 Meet U,” followed by a J Dilla rarity by request, “Take Dem Clothes Off,” which was an absolute banger I admittedly hadn’t heard before. The hosts took some time to acknowledge those in the crowd hearing these songs and/or artists for the first time, as that was part of Drake’s intention with this show, to put his fans on to those who came before him but may not have been as well known.

Being sure to blend in the RnB with the rap, Glenn Lewis would be next up on stage. A master crooner, Glenn Lewis absolutely crushed his live vocals while adapting to surprise song selections by the DJ. I may not have been familiar with all his songs, but he definitely got the crowd in a groove as he closed out his 3-song set with the Juno award-winning classic “Don’t You Forget It,” nailing the high notes. The host had introduced Glenn Lewis to the stage by saying he gets calls to open for Stevie Wonder whenever he’s in town, and we all learned why tonight if we didn’t already know.

Following Glenn Lewis would be the first surprise guest of the evening, Infinite. A former member of the rap group Ghetto Concept, Infinite would celebrate his 25th year in the game by quickly performing a couple songs off his 1998 solo EP 360, “Take A Look” and “Gotta Get Mine.” This brought us back to the days when all Toronto Hip-Hop was considered underground, bringing that raw feel to the stage.

Quickly flipping the script back to RnB, next up would be the lead singer from In Essence, Dru. Joined by two female dancers, Dru would sing his way through some of his solo songs and would bring the sex appeal to the stage with the choreography he had with his dancers. While I wasn’t at all familiar with the songs, Dru put on an incredible show, and he would cap it off by bringing out the rest of In Essence to perform their 2003 hit together “You Will Never Find (Another Love Like Mine),” the 5-man group nailing their choreography.

Continuing on with the RnB vocalists, Shawn Desman would bring more of a Pop flavour to the stage. I personally hadn’t listened to his music since I was twelve years old, during the Much Music era, but the level of talent that he brought to the stage was much greater than the preteen version of me remembers, as he got the energy levels in the building cranked with his performance. Rocking hits like “Get Ready,” “Shook” and “Spread My Wings,” Shawn got the ladies grooving as he nailed his high notes and still had fly dance moves. He shouted out with confidence that he was going to blow the roof off as the beat for “Let’s Go” dropped, the thumping bass bringing that dance energy, and he’d eventually close out his medley of hits with “Electric,” bringing his daughter out to dance with him during the song as the crowd turned up.

Another surprise guest would bless the crowd, as Melanie Durrant came out and killed the stage with her Kill Bill-inspired rendition, “Bang Bang.” While Kardinal Offishall didn’t come out to rock his guest verse on the song, Melanie gave a wicked vocal performance that captivated the crowd. She would however be followed by the Queen of Canadian RnB, Jully Black. Jully would run through a medley of her hits, pulling out a surprise by singing her feature on Nas’ “Heaven” and letting Nas’ first verse play out (bringing back memories of seeing Nas perform at Beer Fest the week prior). With a time slot that may have been too short for her stature, Jully could only perform snippets of fan favourites like “Sweat Of Your Brow” and “Seven Day Fool,” cutting the songs off abruptly after one verse each. She did talk about the challenge of choosing which hits to perform, mentioning her collaborations with Choclair and Kardinal Offishall, but then decided to end her set with a cover of Bob Marley’s “Don’t Worry About A Thing,” getting the crowd to tap into their inner child and sing along.

While DJ Kemo of the Rascalz could be seen setting up his gear, next to hit the stage would instead be another Toronto legend, k-os, bringing back that early 2000s Hip-Hop. He’d start off with an off-the-top freestyle, dropping names of some of the other artists in the building, before getting down to his classic “Superstar Pt. Zero.” Telling the crowd he has hits for days like Drizzy, k-os would tease some of his Juno award-winning, platinum-certified classics like “Crabbuckit” and “B-Boy Stance,” but would go on to actually fully perform “Man I Used To Be” instead, with a B-boy dancing on stage next to him. Slowing it down, k-os would pull out a throwback routine showing a genius musical mash-up, singing his song “Heaven Only Knows” over the guitar riff from Led Zeppelin’s “Stairway to Heaven,” although this time it was a recording rather than live guitar. Drake could be seen getting hype at the side of the stage as k-os rocked the classic.

k-os would turn it up again by performing CatDiesel, getting deep into his performance and even falling to the floor while singing. He’d then notice Drake turning up on the sidelines and decided to pull him onto stage, letting Drake perform what would be his only song for the evening with 2011’s “Headlines.” Not expecting to perform, Drake mostly let the crowd sing along with him and took some time to talk about how k-os’ 2002 album Exit was one of his biggest influences. He’d then ask k-os finish on a high note, which of course led to the upbeat “Sunday Morning,” the crowd turning all the way up. k-os would pull out an electric guitar midway through the song and attempt to play along while singing, although it wasn’t hooked up properly and no sound was coming as he strummed the strings. Having missed the opportunity to play the guitar, k-os tossed it down on the stage like a true rock star and continued to slay the vocal performance regardless, ending his set by tossing out roses into the crowd from a bouquet that was tossed on stage.

The showcase of Toronto Hip-Hop excellence would continue, as Choclair took the stage next and performed a few songs from his Juno award-winning 1999 album, Ice Cold. All hard-hitting, raw raps, Choclair rocked the songs “Flagrant,” “Rubbin’,” and got the crowd to wave their arms to the classic “Let’s Ride,” bringing back memories of when we saw him perform in Mississauga the night the Raptors won the Eastern Conference Championship in 2019. It would have been dope to see Saukrates come out to perform his features on these songs with Choc, but instead Big Soxx waited to come out for his own set list next.

Saukrates’ set would be filled with some dope moments, as he ran through a medley of his own classics like “Father Time,” “Hate Runs Deep,” and “Money Or Love.” He’d bring his wife on stage and dedicate a song to her, explaining to the crowd how he came straight from his father’s funeral (R.I.P.) to perform at this show and how she kept him together through it. To close out the set, he’d bring a bathrobe-wearing k-os back out to perform their song together “On The Run (I Wish I Knew Nathalie Portman),” although it seemed like they didn’t rehearse and had to restart the song midway to get it right.

Taking it out west, next up would be Vancouver’s own Rascalz, the group responsible for one of Canadian Hip-Hop’s most groundbreaking hits, and influencing the cultural shift of having Hip-Hop accepted in Canadian mainstream media. DJ Kemo was ready to go, and he brought out emcees Red1 and Misfit to rock their 2002 hit “Crazy World.” The Rascalz’ set would take them through the years, going back to 1997 with “Soul Obligation,” DJ Kemo flipping the beat to Nas’ “Made You Look” during Red1’s verse for some added energy. They’d then go back to their very first single and music video from 1993, “Really Livin’,” really bringing the history to History. Their set would also include special guests, as Shawn Desman returned for the remix of “Movie Star,” and k-os came back in yet another new outfit for 1999’s “Top Of The World,” with Drake joining them on stage playing hypeman. Rascalz had a short set, but it wouldn’t be the last we saw of them for the evening.

With Hip-Hop getting plenty of representation between the last four acts to hit the stage, Drake would return to say a few words before shifting the night back to RnB. He’d shoutout DJ Starting From Scratch, who inspired Drake to put this show together by having a mix show with all these artists’ songs. Drake would also then introduce the next artist to the stage, who he described as his first girlfriend and one of Toronto’s daughters, Keshia Chanté.

Another artist I hadn’t listened to since high school, Keshia Chanté had a similar effect as Shawn Desman, showing that she still has incredible vocal chords as she got the crowd grooving. Her set would mostly revolve around her Juno award-winning debut album, 2004’s Keshia Chanté, as she performed the singles “Does He Love Me,” and “Bad Boy.” Between these two songs were a couple joints even the hardcore Hip-Hop heads could appreciate, as she performed “Unpredictable,” which uses the same sample from 2Pac’s “I Ain’t Mad At Cha” to give it a smooth RnB twist, and “Shook,” which samples Mobb Deep’s “Shook Ones,” the bass making the building shake. Pardon my being unfamiliar, but hearing these songs for the first time and how the samples were flipped was mind-blowing.

Keshia would close out her set with a performance of her 2006 single “Been Gone,” and Drake would return to take over the emceeing duties. With it now being well past 1am, Drake had to coordinate the last few artists to make room for everyone to bless the stage, as he had a few more surprises in store for the Toronto crowd. He’d next bring up the first notable female emcee to come out of Canada, Michie Mee, who he flew in from Jamaica specially for this show. Representing for that late ’80s/early ’90s era, Michie Mee would rock the house with a handful of songs, including the classic “Jamaican Funk – Canadian Style,” and was ready to keep going in if it weren’t for Drake needing to give everyone a fair time on stage. With a few more shells to unload, as he’d describe it, Drake would bring out Jelleestone to perform his single “Money,” as he tossed out bills into the crowd. After Jelleestone rocked just one song, Drake would next introduce an artist who had a full clip to unload, arguably the artist with the biggest impact on Canadian Hip-Hop besides Drake himself, Kardinal Offishall.

At the start of the evening Drake had told a story about how a pivotal moment that influenced his early career was when Jay-Z was hosting a Caribana concert in 2005 and brought out Kardinal Offishall to rock the crowd. On a night when Jay-Z was trying to promote his newly signed artists at the time, Tierra Marie and Rihanna, he may have underestimated Kardi’s ability to own a stage, especially in his hometown, but this crowd tonight knew exactly who and what they were about to see. Joined on stage by Solitaire as his hypeman, Kardinal immediately got the crowd hyped again by rocking his verse from Clipse’s “Grindin’ Remix,” and with incredible crowd control and showmanship getting damn near everyone in the building to jump during his single “Clear!.” Seeing Kardinal and Solitaire work together on stage felt similar to seeing Busta Rhymes and Spliff Star.

Kardinal would perform another throwback with “BaKardi Slang” before getting his DJ to play the 1970s version of “Tide Is High,” with the crowd singing along. This usually leads into a performance of his 2008 interpolation with Rihanna on the hook, but with time running out he decided to skip this song in favour of some live collaborations. While Rihanna wasn’t in the building, Kardi did have an entire roster of Canadian legends standing off to the side and back of the stage, and he’d choose Jully Black to rock the classic “Money Jane” with him, a rare collaboration to see live on stage. You could tell that this show was truly curated by Drake, as the beat for “Ol’ Time Killin'” nearly dropped before Drizzy had the DJ cut it off, saying it was too early for such a live chune. Kardinal took the opportunity to big up Drake with a speech about his work ethic and drive to become the greatest, and eventually got the entire room singing along as he performed the ’08 classic, “Dangerous” instead.

Drake would later explain that when he planned this event, he wanted to be the one to drop the biggest joints of the evening, and he made it epic by getting the stage lights and house lights turned off, phones in the crowd lit up before dropping the beat to “Ol’ Time Killin’.” Kardinal, Solitaire and Jully Black rocked the joint in the dark, and the energy was as hyped as it had been all night as they killed that classic. There was at least one more iconic song we were expecting from Kardi, but before we got to that, Drake would have yet another surprise in store for the crowd, one last clip to unload as he put it. Drake took the time to reiterate how much of an influence each artist on stage was for both himself and the city’s culture as a whole, and would bring out one last superstar to shock the crowd with: Nelly Furtado.

Rarely ever making public appearances on stage, Nelly Furtado made an exception for this special event and came out to “Promiscuous,” although the crowd did most of the singing for her. Drake told her to treat the crowd like a choir, and so we all sang along with her as she filled in a bar or an adlib here and there to “I’m Like A Bird,” Drizzy even helping her out with the chorus. It was a quick but special appearance, as the crowd deservingly treated Nelly Furtado like Canadian royalty.

Now after 2am with the clip fully unloaded, Drake would ask the crowd if they knew the only song they could possibly do to top what just happened on stage. That of course had to be what he called the Canadian Hip-Hop National Anthem, which was of course the Rascalz’ 1998 single “Northern Touch,” featuring Choclair, Checkmate, Thrust, and Kardinal Offishall. In 1998 these were some of the biggest emcees to represent Canada, connecting the east to the west, Toronto to Vancouver, and uniting the culture across provinces to make one of the most epic posse cuts in Canadian music history. This is Canada’s equivalent to Marley Marl’s “The Symphony.” Every single artist on the song minus Thrust was in the building to perform their verses, and they all rocked it with the most energy, the crowd recognizing the significance of the moment and snapping footage while turning up. This moment alone was worth well beyond the $20 ticket, never mind the near four hours of live music that came before it.

Drake would take some time to again thank all the artists on stage, who had now all gathered in the back of the stage while Kardi and crew killed that last song, and would talk about what this moment meant to him before saying goodbye to the crowd. This moment fit the name of the venue, as it was absolutely historical having all these iconic artists celebrated in the same space together. Having long been called the “screwface capital,” it was refreshing to see Toronto’s Hip-Hop scene united and supporting each other without letting the competition pull them apart, something Kardinal preached during his performance. It was also incredible to see the world’s biggest music star in Drake pay it forward to the artists who came before him, who built the bridges and fought the battles so that he could have a platform to stand on. Drake was visibly humbled to have all his Canadian idols united together for this event, and you could tell he selflessly did this for the city and for the culture as he respectably gave them all their flowers.

Taking time to reflect on the influence each of these artists has had on Toronto culture, this event brought it all together and put it in your face. With Caribana festival in full effect this weekend, you could see on stage how the vast majority of Canada’s major Hip-Hop and RnB artists over its history are mostly Caribbean, with roots going back to Jamaica, Trinidad, or Guyana. Drake was absolutely right in his speech when he said that the way we talk, the food we eat, and the way the city so openly celebrates Caribbean culture is largely influenced by our music. This was an epic celebration of our culture’s history that will unlikely get repeated with all the rarities that took place.

Happy Caribana!

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