In the rapidly evolving landscape of modern hip-hop, few events have captured the raw energy of the underground quite like First Class Fest. In just four years, co-founders Leo Strang and Jake Pretorious have scaled the Toronto-based event from humble beginnings into one of North America’s most significant showcases for emerging talent. The journey, however, has been anything but conventional, defined by the high-stakes pressure of managing volatile schedules and the relentless pursuit of building a sustainable platform for the next generation of rap stars.
The Challenges of Underground Festival Production
The reality of festival management was laid bare just days before this year’s event, when headliner Nettspend withdrew from the lineup. With other artists like Che and Black Kray also canceling, the organizers were forced to pivot instantly. “You can do everything in your power from a legal and contractual standpoint, from an effort standpoint, but sometimes people just don’t want to do things,” Strang reflects. The solution was a testament to their resourcefulness: they tapped OsamaSon, the star of The FADER’s documentary Psychotic, to perform a second, unique setlist, ensuring the festival maintained its momentum.
Building a Community from the Ground Up
The partnership between Strang and Pretorious began in 2022, born out of a shared frustration with the lack of infrastructure for underground rap in Canada. After meeting at a party following a canceled Playboi Carti show, the two quickly realized their complementary skill sets—Strang’s background in digital marketing and Pretorious’s experience in studio management—could fill a void in the local scene. Their early days involved touring Ontario in an RV, performing in frat basements, and learning the ropes of the industry through trial by fire.
“We want to grow the underground scene in Canada,” Pretorious explains. “There’s so much talent in Canada, all over Canada, but there’s not a lot of spotlight on it.” This mission has led them to champion artists like Amo, Pnkrok, and Bronclair, providing a stage for voices that are often overlooked by mainstream promoters.
Looking Toward the Future
Planning for the latest iteration of First Class Fest began 14 months in advance, marking a significant leap in scale for the duo. Securing a venue capable of hosting 1,500 attendees was a daunting milestone, but it proved their readiness to operate at a higher level. Despite the chaos of backstage logistics—including a tense moment where police threatened to shut down the show during Apollo Red’s set—the organizers remain focused on the bigger picture.
For Strang and Pretorious, the reward lies in the moments of genuine connection, whether it is a supportive word from an artist like Tezzus or finally securing a photo with Lucki after a hectic performance. As they continue to refine their process, First Class Fest stands as a beacon for what is possible when passion and professional rigor meet in the underground.
