The energy was electric last Sunday as dozens of Toronto’s hip-hop pioneers gathered outside the Rogers Centre for what many are calling a historic moment in the city’s music legacy. As the photographer’s flash illuminated faces that helped build our city’s distinctive sound, I couldn’t help but feel the weight of cultural history unfolding before my eyes.
“This is about more than just a photoshoot,” explained DJ X, a fixture in Toronto’s club scene since the early 90s. “We’re documenting a movement that shaped this city’s identity when nobody was paying attention.”
The ambitious project, coordinated by local music historian Karla Thompson, brought together over 70 artists spanning four decades of Toronto hip-hop development. From early innovators who performed at the Concert Hall in the 1980s to current chart-toppers, the gathering represented a comprehensive timeline of the city’s distinctive contribution to global hip-hop culture.
“You can’t talk about Toronto’s cultural evolution without acknowledging how hip-hop transformed neighborhoods like Scarborough and Jane-Finch,” Thompson told me as she directed artists into position. “Before Drake put us on the international map, these artists were building something authentic from the ground up.”
The significance of documenting this history becomes apparent when considering recent data from the Toronto Arts Foundation, which shows that 68% of the city’s musical heritage remains undocumented compared to other cultural expressions. This photoshoot serves as both art and archive—capturing faces that might otherwise be forgotten despite their cultural contributions.
What struck me most was the intergenerational camaraderie on display. Legendary MC Maestro Fresh Wes shared laughs with newer artists like Haviah Mighty, demonstrating how Toronto’s hip-hop community has maintained its connectedness despite evolving styles and approaches.
“We didn’t have the internet when we started,” explained producer Kardinal Offishall between poses. “Everything was word of mouth, mixtapes passed hand to hand. That created a different kind of community than what exists today.”
The Toronto Public Library has expressed interest in featuring the finished photographs as part of their upcoming exhibition on local music history. This institutional recognition represents a significant shift in how the city acknowledges hip-hop’s cultural importance.
City Councillor Matlow, who attended the event, emphasized this point: “Toronto’s global reputation as a music city owes a tremendous debt to these artists who persevered when there was little infrastructure supporting them. This documentation matters for our collective understanding of who we are.”
Behind the scenes, Thompson’s team recorded oral histories from participants, creating what will become a comprehensive multimedia archive of Toronto’s hip-hop evolution. These firsthand accounts reveal the challenges of building a scene in a city that initially provided few venues and limited radio support for local artists.
“We used to perform anywhere that would have us,” recalled rapper Michie Mee. “Community centers, school gymnasiums—wherever we could connect with our people. That hustle is part of Toronto’s hip-hop DNA.”
The project also highlights the distinctive multicultural character of Toronto’s hip-hop expression. Unlike scenes dominated by a few cultural influences, our city’s hip-hop incorporated sounds reflecting our immigrant communities—Jamaican patois, Filipino samples, East African rhythms—creating something uniquely Torontonian.
University of Toronto music researcher Dr. Francesca Williams, who attended the photoshoot as an observer, noted: “What makes Toronto’s hip-hop story compelling is how it reflects our city’s immigrant narrative. These artists were code-switching between cultural identities long before that concept entered mainstream discussion.”
As the sun began setting over the Rogers Centre, I watched artists exchange contact information and plan future collaborations. This wasn’t just documentation of the past but a catalyst for new creative partnerships.
The completed photographic collection will be unveiled at a special exhibition at the
