From NYC to Croatia: How Uncle Delroy became one of Toronto’s fastest-growing Caribbean events

It has only been three years since Uncle Delroy burst onto Toronto’s Caribbean events scene, but the homegrown brand has already expanded into an international phenomenon, bringing its signature Dancehall Karaoke experience to cities including New York, Los Angeles, London and even Croatia.

Launched in 2023, Uncle Delroy reimagined traditional karaoke by centering it around Jamaican dancehall music and Caribbean culture. 

What started as a niche event has since evolved into a series of sold-out parties, block parties and cultural experiences that have become staples for Toronto’s Caribbean community, and anyone who appreciates the culture.

Now, the brand’s reach extends well beyond Canada, with organizers saying demand from international audiences has fueled its rapid expansion.

“We had tons of people from all over the globe saying, ‘Hey, we want you to come,'” Ashley Henry, one of Uncle Delroy’s planners, known affectionately as one of the brand’s “nieces” told Now Toronto. “So it’s essentially just people asking, and us giving them what they want.”

Uncle Delroy’s reaching nieces and nephews beyond Toronto’s borders 

Henry said Uncle Delroy’s first international event took place in New York City in October 2023. Since then, the team has returned to the city several times, cementing it as one of the brand’s biggest markets outside Toronto.

“We’ve been back to New York about six times now. That’s essentially our second home outside of Toronto,” she said.

For fellow planner and “niece” Ilya Mogge, watching Uncle Delroy evolve from a karaoke night into a globally recognized event series has been both exciting and surreal.

“It’s really high energy, but that feeling is still there of familiarity and community and laughter and fun,” Mogge said. “The energy has changed, but the feeling is still there.”

That sense of nostalgia, Henry says, has always been at the heart of Uncle Delroy’s success.

“We bring back the vibes and the songs that people are super familiar with, like the 2000s or early 2010s,” she said. “People are always like, ‘Yeah, this is when dancehall was at its peak.'”

Whether the event is held in Toronto or overseas, organizers say audiences have embraced the same sense of community. For Mogge, one of the most memorable stops has been Croatia, where Uncle Delroy discovered a passionate European fanbase.

“Croatia was amazing,” she said. “A lot of the attendees were European, so it was nice knowing that across the globe, the feeling and the experience is still the same. I love finding new cities where we’re like, ‘Oh, this is family too.'”

The team plans to return to Croatia in 2027, while continuing to explore new markets. Henry says Fort Lauderdale is high on her list for future events, but one destination stands out above the rest.

“My ultimate goal would definitely be Osaka or Tokyo,” she said.

Stacked weekend in store for Uncle Delroy during Toronto’s Carnival season

Before setting its sights on new cities, however, Uncle Delroy is focused on one of the busiest weekends of the year in its hometown.

The brand has several ‘Delroybana’ events planned throughout Toronto’s Caribbean Carnival weekend, including its highly-anticipated Bana Block Party, which has become so popular this year that organizers say it has a waitlist of roughly 3,000 people. The festivities will wrap up with the signature Dancehall Karaoke event on Sunday.

For Henry and Mogge, the rapid growth of Uncle Delroy has been rewarding, but they say the mission has remained unchanged: creating a space where people can reconnect with the music, culture and community they love, whether that’s in Toronto or halfway around the world.

Those looking to keep up with upcoming events and future international dates can visit Uncle Delroy’s website for the latest announcements.