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The Drake Hotel is Entering a New Era of Music and Culture
A cultural hub and hotspot spanning well over two decades, The Drake Hotel continues to evolve.
A historic hotel on Toronto’s Queen West, The Drake became a boutique hotel hotspot in 2004 — known not just for its chic aesthetic, but its music, art, and culture. Tucked beneath the hotel — which opened a new Modern Wing in 2021 — is The Drake Underground, an intimate music venue that has been home to some of the city’s most legendary shows for the last two decades.
In the 1980s and ‘90s, the space was a rave den and a punk bar — becoming a staple for the city’s nightlife scene. It became an official music venue in the early 2000s and has hosted major global talent, from Billie Eilish to M.I.A. Many Canadian heroes have had essential early shows there, from Broken Social Scene to BadBadNotGood, Rich Aucoin and more.
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In its two decades of programming, The Drake has continued to push boundaries, representing musicians of all genres coming to connect with an eager crowd of 150 — an element of the venue that makes it small but mighty.
“It's an opportunity to see a show in a very intimate environment, but with incredible audio, visual and talent,” shares Ana Yuristy, The Drake Hotel’s Chief People and Brand Officer. “It has a storied history of live acts and entertainment in the city, going back many years.”
The Drake’s music programmers have played an integral role in tapping about-to-break artists. Yuristy calls the role “a curator of talent.” They’re able to tap artists that are on the verge of breaking out, so you know when you're seeing a show at the Underground, the artist could be the next big thing.
BadBadNotGood, What's In The Box Music Festival (2012)Courtesy Photo
Earlier this year, Duane Bobbsemple joined the hotel team as the Music and Culture Programming Manager. Growing up, Bobbsemple, whose parents are from Jamaica and Guyana, was immersed in a musical household, playing piano and guitar. His father was a DJ with a massive record collection. With his company Banded Purple, he’s spent the last few years spotlighting up-and-coming artists reflecting the diversity of Toronto right on its streets, in subways and non-traditional galleries through the West End.
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Coming to The Drake was a perfect fit. As a resident of the Parkdale neighbourhood, Bobbsemple recalls seeing the early 2000s renovation firsthand and considered the hotel to be “a cultural landmark within the city,” jumping at the chance to elevate the venue’s music programming when the opportunity arose.
In his newly appointed role, he says he plans to continue the hotel’s nightlife legacy while focusing on integrating Gen Z talent into the space, who might not be as familiar with the long-running venue.
“We want to create that bridge as they're the trendsetters and tastemakers of what's next,” he explains.
This includes implementing more globally diverse sounds, including African and Punjabi music — both of which are on the rise within the Canadian music industry. For the spirit of acts The Drake is looking to nurture and grow in the Underground, he shouts out River Tiber, 100 gecs, Jakob Lomiel, Kadhja Bonet, Cruza, KESH, 3Li¥en and Erika de Casier for their diverse and progressive voice.
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As a music programmer, Bobbsemple works with promoters to book artists, while going out to shows and scouting the talent throughout the city and beyond. The new team has started filling out its event calendar for the following months, including an Afro-French DJ set, a “curated open mic night” and shows from emerging singers like Mikayla Geier and Baby Nova. The multi-decade-running indie music institution, Elvis Monday, will also make its return.
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“I want to reflect the city that we live in. It’s super diverse. It's vibrant, it's always evolving,” he says.
Always evolving is the name of the game for The Drake, which has recently started collaborations with multiple Canadian culture juggernauts. This past summer, it launched a partnership with independent record label Wax Records to create an interactive record wall with vintage LPs that resided on the hotel’s rooftop patio, The Sky Yard.
“It was really an engaging piece. We hope in the future we'll be able to do live performances with Wax Records — that partnership continues to evolve,” Yuristy says.
The Drake SkyYard x Wax Records (2025)Courtesy Photo
In September, as an official hospitality partner of the Toronto International Film Festival (TIFF), the hotel hosted “official–unofficial TIFF after parties,” with themed beverages, bites and a dancefloor bumping with the beats of local DJs, singers in the genres of R&B, afrobeats, amapiano, dancehall, hip-hop and house. The Drake was a party hotspot for celebrities and film industry power players.
Continuing to elevate its position as a key element of Toronto’s nightlife scene is just the beginning for Bobbsemple’s role.
“It’s important for me to start creating experiences that feel more international and globally relevant,” he says. “That put The Drake on the map as a destination for its programming.”
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