The OVO dancehall connection is not a passing phase or a genre-tourist experiment. It is a documented, decade-and-a-half relationship between Toronto rapper Drake, his October’s Very Own empire, and the Jamaican sound that helped reshape global pop music.
From early Jamaica video shoots to record-label signings to sold-out Scotiabank Arena nights with Vybz Kartel, the evidence is everywhere. This article maps the full timeline, track by track and year by year.
What Is OVO Sound, and Why Does Dancehall Fit?
OVO Sound is a Canadian independent record label founded in 2009 by rapper Drake, producer 40, and manager Oliver El-Khatib. Its genre fingerprint has always been wider than hip-hop alone.
The label’s listed genres include hip-hop, the Toronto sound, trap, R&B, and dancehall, that last entry is not incidental. Toronto’s Caribbean diaspora is one of the largest outside the islands themselves, and dancehall has been embedded in the city’s cultural fabric for generations.
Very few artists outside of Canada hold as deep a cultural grip on Toronto as Vybz Kartel, whose music has been the pulse of Caribbean diasporic life across the city for over two decades, from basement jams in Scarborough to Caribana. Drake grew up inside that cultural reality.
2011: The Foundation Is Laid in Jamaica
Drake had been flirting publicly with the idea of doing dancehall or a dancehall project at least since the top of 2011, a moment that started with a video shoot in Jamaica and proceeded through closer and closer ties between OVO and dancehall artists like Mavado and Popcaan.
That Jamaican trip planted a seed that would take several years to fully bloom commercially, but the directional intent was clear from the outset.
The title of Drake’s 2017 playlist project, More Life, itself carries a trace of dancehall lineage. More Life” is a Jamaican slang phrase used to wish someone well, popularized by dancehall artist Vybz Kartel, whom Drake has called one of his “biggest inspirations” for his own dancehall-inflected sound.
2013: Popcaan Shoots a Video in Toronto
Before any formal business arrangement existed, the geography began to collapse. While in Canada, Popcaan connected with Canadian rapper Drake, who expressed his admiration.
In 2013, Popcaan released the video for “Unruly Rave,” which was shot in Toronto, Ontario, and directed by October’s Very Own label head Niko.
That video shoot, produced under OVO’s creative umbrella, was an early organizational signal that the relationship between Unruly Entertainment and OVO was more than a casual fan connection.
2015 to 2016: “Know Yourself,” “Controlla,” and the Rihanna Moment
The OVO dancehall connection gained its first formal credits during the Views era. Over a three-year stretch, Popcaan had an outsized influence on Drake’s music, he featured on the outro of 2015’s “Know Yourself,” appeared on the leaked version of 2016’s “Controlla,” was interpolated on “Too Good,” and various parts of his slang and vocal delivery made it onto More Life.
The story of “Controlla” is particularly instructive. Prior to the album’s release, “Controlla” was one of two tracks from Views leaked online; the leaked version featured dancehall artist Popcaan.
The song was still included on the album without Popcaan’s contributions and with an additional Drake verse plus a Beenie Man sample. The final single was released on June 7, 2016, and is genre-classified simply as dancehall.
But the song that made the OVO dancehall connection impossible to ignore was “One Dance.” Released on April 5, 2016 and credited to Drake featuring Wizkid and Kyla, the track is classified as pop dancehall and afrobeats. “One Dance” was the first of three dancehall singles to be released from Views, along with “Controlla” and “Too Good.”
Released on April 5, 2016, “One Dance” sold over 10 million units and holds the record for being Drake’s first song to reach number one in over 15 countries, including the United States, Australia, Germany, Ireland, France, Canada, the Netherlands, New Zealand, and Switzerland.
Despite the song’s wild success, its release was a cautious experiment by the Canadian rapper, who considered the dancehall track, his first as a lead artist in the genre, a daring deviation from his known works.
That caution proved unfounded. With 3.3 billion streams and counting, “One Dance” remains Drake’s biggest track on Spotify. The single went diamond in 2022, and has gone platinum additional times since.
The chart-topping single is from Drake’s six-times platinum album Views, which sold over seven million units worldwide, making it one of his most commercially successful projects.
Rihanna’s “Work” contributed to the same cultural moment in 2016. There is no three-song combo stronger in Drake’s collaborative catalog than “Controlla,” “One Dance,” and “Work.”
The collaboration with Rihanna feels natural: Caribbean culture has heavy roots in Drake’s native Canada, but working with a Barbadian like Rihanna also gave Drake the confidence to go all-in with a dancehall-influenced style.
2017: More Life and the Dancehall Playlist Project
If Views mainstreamed the OVO dancehall connection, More Life deepened its texture. The 2017 playlist project leaned heavily into patois phrasing, riddim-adjacent production, and the London-to-Kingston sonic corridor Drake had been cultivating.
The more consistent critical observation about Drake during this period was that he was overly calculating about forming strategic alliances in the scenes he moved in and out of, as if he was playing a world-spanning chess game with Black Atlantic culture.
Whether one reads that as critique or as evidence of serious cultural investment, the More Life credits made the OVO-dancehall axis impossible to dismiss as superficial.
2018 to 2019: The Popcaan Signing
The relationship formalized on December 23, 2018, at Unruly Fest in St. Thomas, Jamaica. Drake, the Toronto rap superstar, shared the news on stage during a cameo at the Unruly Fest in Jamaica where Popcaan was performing. “I just want to let everybody know, finally, officially, 2019, Popcaan is signed to OVO,” Drake told the crowd.
Popcaan had long framed the relationship in familial terms. “OVO is straight up family because Drake was the one that said OVO Unruly,” Popcaan said.
Drake has me as Drizzy Drake in Jamaica. So when I view Drake as a young youth that is doing well in the game it’s the same way I view myself also.”
From the Grammy’s side, Popcaan saw the Drake link as instrumental for the rapid growth of his own career as well as the international expansion of dancehall itself. “By being around Drake and the whole connection, it gave me a lot of exposure,” Popcaan told GRAMMY.com.
Drake’s decision to sign the Jamaican musician marked the first time he had added to his OVO Sound imprint since bringing on artists Baka Not Nice and Plaza in 2017.
2020: Fixtape and Two New Dancehall Tracks
The signing quickly yielded collaborative output. Popcaan unveiled his mixtape Fixtape in August 2020, and the dancehall project featured two new collaborations with Drake, titled “All I Need” and “Twist and Turn.”
Fixtape saw the Jamaica-born star taking dancehall into rap and R&B territory with the assist of key collaborators including French Montana, PARTYNEXTDOOR, and, most notably, Drake, whose OVO Sound label released the project.
2023: “We Caa Done” and Great Is He
The most recent landmark in the Popcaan chapter arrived at the start of 2023. We Caa Done” is a song by Popcaan featuring Drake, released on January 6, 2023 through OVO Sound, as the lead single from Popcaan’s fifth studio album Great Is He.
The song was written alongside Tresor, who produced it with Batundi. Drake gave the dancehall star a major boost to start 2023, with “We Caa Done” being the first song released by OVO Sound that year.
2025: Vybz Kartel Comes to Toronto
The most symbolically loaded chapter in the OVO dancehall connection arrived in October 2025, when Drake orchestrated Vybz Kartel’s first-ever performances in Toronto.
Drake’s OVO presented Kartel’s concerts in Canada, a series that stretched across multiple nights. Since his release from prison in July 2024, Kartel had wasted no time reclaiming his crown, consistently performing for sold-out audiences around the globe.
The groundwork for the Toronto run had been laid at Wireless Festival in London earlier in the summer. Kartel joined Drake onstage for a rendition of “Summer Time” in mid-July at the Wireless Festival.
The 6 God made an onstage appearance at Vybz Kartel’s OVO-presented concert in Toronto on Sunday night, October 26, celebrating the first of the Jamaican star’s three sold-out shows at Scotiabank Arena.
Drake’s words from the stage that night captured the depth of his personal connection to the music: “I used to hand out flyers outside of a club called Escape just to go inside to the club and listen to your chune. So one more time, please as a city, as a family, make some noise. The Worl Boss is deya,” Drake said.
Few artists outside of Canada hold as deep a cultural grip on Toronto as Vybz Kartel, whose music has been the pulse of Caribbean diasporic life across the city for over two decades. His catalog has soundtracked generations of Toronto youth, and that influence is reflected in the city’s biggest musical representatives.
Why the OVO Dancehall Connection Matters
The story arc from a 2011 Jamaica video shoot to three sold-out Kartel nights at Scotiabank Arena is not one of opportunistic genre tourism.
It is a sustained, reciprocal investment that runs through actual label infrastructure, co-written and co-produced records, and the lived experience of Toronto’s Caribbean community.
Drake’s uncanny ability to reach unexpected and enviable heights of success with dancehall music remains an elusive dream for many established and budding dancehall acts, who continue to experiment with other genres due to pure dancehall’s perceived limited commercial viability.
By extending the weight of OVO Sound’s commercial machinery to artists like Popcaan and by personally presenting Vybz Kartel’s Toronto debut, Drake has done what few hip-hop figures have managed: he turned structural admiration into structural support.
The OVO Fest 2025 Kartel announcement highlighted Toronto’s Caribbean roots, underscored dancehall’s global reach, and reinforced Drake’s role as a cultural connector.
Toronto has one of the largest Caribbean diasporas outside the islands, making Kartel’s debut in the city especially significant.
The OVO dancehall connection, in other words, is not a side note to Drake’s career. It is one of its load-bearing walls.
