Of course I’d find myself at a Hip-Hop block party to ring in the new year. In 2024 I moved to a new home in Mississauga, and it felt right closing out the year with a Hip-Hop concert right here in my new stomping grounds. The free outdoor event would take place in Celebration Square and featured artists representing multiple generations of Canadian Hip-Hop. The lineup included the OG himself, Maestro Fresh Wes, the 2000s veteran Shad, and relatively newer artists with Toronto’s DijahSB and Mississauga’s own AR Paisley. This may have been the biggest Hip-Hop concert in the GTA for Hip-Hop heads to get their fix for live music on New Year’s Eve.

Despite the cold weather and rain coming down for most of the night, plenty of groups congregated in Celebration Square for the family-friendly event. The Square had an ice rink for skating, plenty of food trucks, and of course there would be fireworks at midnight to ring in the new year. Hosts Mariah Amber and Rebecca Tandon would set the stage, along with DJ Andre 905 spinning party tracks, and they’d announce that the City of Mississauga was celebrating its 50th anniversary, which happened to coincide just one year off from the 50th anniversary of Hip-Hop culture, making the inclusion of Hip-Hop music that much more tasteful.

Starting off the concert portion of the event would be none other than Maestro Fresh Wes, who was celebrating recently becoming the first Hip-Hop artist to ever be inducted into the Canadian Music Hall of Fame. Most know him for being among the first emcees to put Canada on the map within Hip-Hop circles in the late ’80s, but some may not know that he started releasing a series of children’s albums called Young Maestro in recent years, using Hip-Hop music as an educational tool. His setlist early in the evening would be focused around that, as he started by performing a few songs off of his latest album in the series, Rhyme Travellers, and got the kids engaged with songs about time travel and dinosaurs.

Although it was a family-friendly event, Maestro wouldn’t stick to the kiddy songs for long, as he’d also acknowledge the parents in the crowd who know him for his ’80s and ’90s throwbacks, and took it back to 1989 with the classic “Let Your Backbone Slide.” You could tell there were real fans in the crowd, as he took a fan request to perform “Drop The Needle” and also did the ’98 classic “Stick To Your Vision.” While Maestro typically rocks the throwbacks when he performs live, he’d use this early-card timeslot to also perform some of his more recent releases, including a 2015 collab with Mississauga’s own JD Era, “Underestimated,” and another high-energy banger from his Young Maestro series that any Toronto Raptors fan could appreciate, “Jurassic Park.”

After bringing a ton of energy to the stage, Maestro would close out with his celebratory 2023 single, “Still Winning,” getting one last wave of energy from the crowd. The party would continue with a “NYE Jr.” celebration for the kids, with confetti shooting out at 9pm for an early celebration before bedtime. There would be a bit of a break until the next artist came out to perform, Toronto’s own DijahSB.

DijahSB is a relatively new artist from Toronto who started making music in the 2010s and released their debut album in 2020, called 2020 The Album. I was unfamiliar with the music going into this show, but the songs had some dope production to them, with a lot of synths and bass that got the crowd moving. DijahSB had some smooth flows as well, although the bass would sometimes drown out the vocals and make it tough to pick up on the bars. Still, songs like “Throw That Back” and “Frontin’ Like Pharrell” had the crowd grooving early on in the setlist.

While we were toughing it out in the cold rain, DijahSB at least kept the good vibes going and had us dancing throughout their set. They kept the crowd engaged with more positive dance vibes on “Exceptional,” and even performed another one of their tracks twice as they saw the fans get familiar with the beat mid-song. It was a quick half-hour setlist, but DijahSB made the most of it and definitely gained new fans with their performance.

After another short break between performers, the next artist to hit the stage would be the Juno, Emmy and Peabody award-winning emcee hailing from London, Ontario, Shad.

Joined by DJ T.Lo, Shad would get right into the positive vibes with songs off of his latest albums, starting with track one off of 2021’s TAO, “Out of Touch,” and the upbeat single “The Fool Pt. 1 (Get It Got It Good)” from 2018’s A Short Story About A War. Having not toured as often since these latest albums came out, much of his setlist would be focused around them, although he did pull out some throwbacks. He’d acknowledge the diversity of the people in the Mississauga crowd before doing the fan favourite “Fam Jam (Fe Sum Immigrins),” and also performed the classic “Stylin'” with an alternate second verse from “TAO Pt. 1,” eventually going acapella for part of the verse.

For anyone who hasn’t seen Shad perform live before, he’s an emcee who puts the focus on lyricism, always rapping every verse without any backing vocals and often going acapella for listeners to pick up on the bars. The next few songs would be bar-heavy with a ton of wordplay, as he performed another TAO favourite “Slot Machines,” complete with the beat-change midway, and also pulled out a new track off of his 2024 EP Reel Speakers, “Keep Going (And Don’t Forget).” Even though 2025 will mark 20 years since Shad’s debut, the new joint showed that he’s still sharp as ever on the mic, with ill rhyme patterns and wordplay for days.

Continuing on with the relatively newer joints in his catalogue, Shad would get the dance vibes going with the first half of “Peace/War,” and had the crowd vibing along to the steady-paced “The Fool Pt. 3 (Frame of Mind).” He’d pull out a mic stand and dedicated the song “GOD” to his parents, who were already in the new year celebrating in Rwanda, and barred-out for another 2024 joint “That’s All, That’s It.” These songs may have been lesser known, being deep album cuts or standalone singles, but Shad would soon bring back the familiar with the 2010 throwback “Rose Garden,” which felt especially fitting with the rain still pouring down. “Along with the sunshine, there’s gonna be some rain, rain, rain sometimes.”

Nearing the end of his set, Shad would return to his TAO album with the single “Black Averageness,” the message of self-acceptance resonating with the crowd, and would spit one more acapella freestyle before closing out with the outro from A Short Story About A War, “All I Need.” By now a huge crowd had filled up the square and the fans were energized off of Shad’s set, ready to continue the celebrations.

Although the hometown artist AR Paisley was set to headline, and all 4 performers were going to unite on stage for a special finale just before midnight, the temperature was dropping and our toes were starting to freeze from being outside in the rain for so long. We opted to head home at this point and watch the fireworks from our condo balcony. While we missed the final part of the concert, we could see there was a massive crowd ready to celebrate the new year and support their hometown artist, with some fans still only now entering Celebration Square.

Overall, this was a great way to close out the year and celebrate local Canadian music. Between Maestro Fresh Wes, Shad, DijahSB and AR Paisley, the crowd who stayed for the whole event got to experience a journey through several generations of Canadian Hip-Hop, from Maestro’s pioneering work in the ’80s and ’90s to Shad’s deep discography covering the 2000s onwards, to the newer artists who are just getting started in the late 2010s/early 2020s. Even though the rain made it tough to stay outdoors, it was still a fun event that any Hip-Hop lover could appreciate. Cheers to 2025!

Check out this playlist of concert videos from all the times I’ve seen Shad perform over the years!

Check out the SYpherSights Youtube channel for more concert videos.

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