Taking Flight: How First Class Fest is Forcing Toronto's Establishment to Listen
AI-generated image · Bay Street Wire
From DIY roots at Parkdale Hall to a 15,000-capacity stadium, Jake Pretorius and Leo Strang are proving that underground rap is no longer a niche interest—it's a cultural powerhouse.
For too long, Toronto's underground rap scene has existed in the periphery, operating in the shadows of the city's formal entertainment industry. But this weekend, that dynamic shifts. First Class Fest is moving into The Bowl at Sobeys Stadium on Aug. 28 and 29, signaling a pivotal moment where the raw energy of youth culture demands a stadium-scale stage.
As blogTO first reported, the festival was founded by 23-year-olds Jake Pretorius and Leo Strang. The duo launched the venture in 2022 with "DIY" beginnings at Parkdale Hall. Their motivation was born from a systemic gap in the industry: underground rappers from Europe and the U.S. frequently bypassed Canada on their tour circuits. Rather than waiting for the establishment to invite them in, Pretorius and Strang decided to throw the shows themselves.
Scaling an underground rap event to a venue capable of holding 15,000 people is an ambitious gamble. Strang told blogTO that a festival of this scale focusing exclusively on underground acts is virtually unheard of. The path to Sobeys Stadium wasn't without friction; the founders cited challenges ranging from a weak Canadian dollar to the inherent difficulty of selling thousands of tickets for artists who typically play in venues with capacities of 1,000 to 2,000.
However, the festival's success is rooted in a broader vision of inclusivity. Rather than targeting a narrow demographic, the founders have curated the event to appeal to various segments of Toronto's youth culture, including the fashion, arts, goth, and underground music communities. This strategy has paid off, with Pretorius noting to blogTO that the event is now "very close to sold out."
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**Aisha's Analysis: The Shift in Power**
In my view, First Class Fest is more than just a concert; it is a declaration. By securing a venue like Sobeys Stadium—an achievement aided by The Feldman Agency—Pretorius and Strang are forcing the city's cultural gatekeepers to acknowledge a movement that has already matured. When you move from a community hall to a stadium, you are no longer asking for permission to exist; you are claiming space.
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The festival's aviation-themed branding—where tickets are "boarding passes" and the countdown is "takeoff"—mirrors the trajectory of the artists on the bill. The lineup features international rapper Sayso, songwriter and singer Lucki, and rapper and producer OsamaSon, with British rapper and singer Lancey Foux scheduled for Day 1.
Crucially, the organizers are resisting the "headliner culture" that often dominates mainstream festivals. By withholding set times, Strang and Pretorius are encouraging attendees to discover new artists rather than "nitpicking" the lineup. As Strang told blogTO, the goal is for fans to "embrace the unknown."
While the festival has already expanded to hubs like Vancouver and Montreal, the founders are focused on sustainable growth. Having built the company "brick by brick," they intend to make First Class Fest a Toronto summer staple, with future eyes on winter editions and eventual expansion into the U.S.