Inside Canada's Biggest Underground Rap Fest

With only three days left before the launch of Toronto’s First Class Fest, co-founders Jake Pretorious and Leo Strang found themselves in a crisis. The festival’s second-night headliner, Nettspend, had dropped out, following earlier cancellations from Che and Black Kray. Navigating the unpredictable nature of live event management, the duo immediately pivoted to damage control. “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, for whatever reason,” Strang explained. “We literally got that Netspend call 20 minutes before he made his announcement. We were immediately just at the drawing board thinking of replacement artists.”

How two 23-year-olds put together Canada’s biggest underground rap fest

The organizers ultimately secured a second performance from Day 1 headliner OsamaSon. Given his status as a defining figure in the current underground landscape, he was the only logical choice to fill the void. Following his unique set, which leaned heavily into rare leaks, the festival successfully concluded with a performance by Lucki. This high-stakes problem-solving is indicative of the resilience required to scale a niche event into one of North America's most significant rap showcases in just four years.

Pretorious and Strang, both 23, first crossed paths in 2022 after a scheduled Playboi Carti show in Toronto was canceled due to border issues. Their shared drive to fill the void in the local underground scene led them to collaborate on a series of grassroots events, including a DIY tour across Ontario. They view First Class Fest not just as a business, but as a necessary platform to elevate Canadian talent that often lacks mainstream exposure. “There’s so much talent in Canada, all over Canada, but there’s not a lot of spotlight on it,” Pretorious noted.

Tezzus and Xaviersobased.Joshua Kaufman / First Class Fest

Pradabagshawty.Joshua Kaufman / First Class Fest

Planning for this year’s iteration began 14 months in advance. The duo leveraged their three years of industry relationships to book a lineup capable of selling out a larger venue, marking a significant leap from their previous capacity of 1,500 attendees. Despite the stress, the festival provided memorable moments of connection, including a supportive exchange with Tezzus during a tense crowd control situation and finally securing a photo with Lucki as he departed the venue.