From Portmore to Toronto: How Vybz Kartel and OVO Rewrote Dancehall History

Recording Artist, Producer, Entrepreneur: Adidja Azim Palmer, Professionally Known As Vybz Kartel, Location: Scotiabank Arena, Toronto, Canada, Year: 2025, Photographer: Ajani Charles

Approximately a 19-minute read.

Outline

Vybz Kartel: The Worl’ Boss in Toronto

The Blue Jays and the Return of a Legend

Drake’s Cameo and Cultural Continuum

The Caribbean Diaspora and Dancehall’s Expansion

Behind the Scenes at Project T-Dot

Humour, Heritage, and the Deejay Tradition

A Testament to Endurance and Cultural Power

Rebuilding Lives and Restoring Hope

Vybz Kartel: The Worl’ Boss in Toronto

My career keeps me too creatively engaged to regularly experience the fear of missing out (FOMO); more often than not, due to fatigue, I experience the joy of missing out (JOMO).

But when Vybz Kartel announced Freedom Street, his 2024 New Year’s Eve concert at the National Stadium in Kingston, Jamaica, I felt genuine FOMO for the first time in years. I wanted to be at his first live performance since his 13 years of incarceration ended.

So when I learned that he would perform in Toronto this October, I was eager to witness and document my favourite dancehall artist live.

On Sunday, October 26, 2025, I had the pleasure of attending and documenting the first of three sold-out Vybz Kartel concerts at Scotiabank Arena.

Live Nation, October’s Very Own (OVO), Tjrecords, and other key stakeholders granted me and other photographers full access to document the entire show, an uncommon privilege without special permission, and I am grateful for their hospitality.

They clearly understood the rarity of Vybz Kartel performing in Toronto and sought to maximize press and social coverage of the event. And rightly so: three or four years ago, such a concert would have seemed impossible anywhere, let alone here.

DJ, Mixer: Ricky Platinum, Location: Scotiabank Arena, Toronto, Ontario, Canada, Year: 2025, Photographer: Ajani Charles

The Blue Jays and the Return of a Legend

After Ricky Platinum, his longtime DJ and friend, ignited the crowd with a blistering set, Adidja Azim Palmer, better known as Vybz Kartel, the Worl’ Boss, made his dramatic entrance wearing a Toronto Blue Jays jersey and stepping out of a mock jail cell as Akon’s Locked Up blasted through Scotiabank Arena. Nearly 20,000 fans erupted in deafening cheers.

The timing was poetic: Kartel performed in Toronto just as the Blue Jays competed in the World Series, symbolizing not only his personal liberation after over a decade behind bars but also Toronto’s own moment of international pride and resurgence.

Once on stage, Kartel delivered a commanding set full of grit, wit, and charisma, performing fan favourites like Fever, Clarks, Go Go Wine, and one of my favourites, Money Pon Mi Brain (C-T Scan), which even mentions T-Dot, aka Toronto.

His performance reminded everyone why he remains one of the most prolific and controversial figures in modern dancehall; a lyrical architect whose work has shaped generations across Jamaica and the diaspora.

The King of Dancehall was back.

Recording Artist, Producer, Entrepreneur: Adidja Azim Palmer, Professionally Known As Vybz Kartel, Location: Scotiabank Arena, Toronto, Ontario, Canada, Year: 2025, Photographer: Ajani Charles

Drake’s Cameo and Cultural Continuum

Drake made several cameo appearances during the first of the three shows, beginning with a brief performance of hits including Controlla, One Dance, Hold On, We’re Going Home, Hotline Bling, Rich Baby Daddy, Which One, and NOKIA.

He performed from a balcony on the west side of the arena, likely within the 300-level suites, alongside his longtime collaborator and business partner Future The Prince.

Seeing and documenting Drake and Future the Prince perform together reminded me of Drake’s humble beginnings; I have watched and documented them sharing stages since 2009.

I have listened to Drake’s music nearly every week since the summer of 2004, and according to Spotify’s data, he is the artist I listen to most. Vybz Kartel is second, even though Prince, Michael Jackson, James Brown, Isaac Hayes, Mariah Carey, the Notorious B.I.G., 2Pac, Jay-Z, Eminem, and Nas have been my favourite modern musicians for decades.

That said, the combination of my deep appreciation for both Drake and Kartel’s music, coupled with my vantage points that night, made me unavoidably biased in my appraisal of the concert.

It is still mind-boggling to me how far Drake’s career has evolved, how wide his cultural reach has grown, and how many rare moments in music and entertainment history he and OVO have created, from Toronto of all places.

DJ, Entrepreneur: Adel Nur Professionally Known As Future The Prince, Recording Artist, Producer, DJ, Actor, Entrepreneur: Aubrey Drake Graham Professionally Known As Drake, Location: Scotiabank Arena, Toronto, Ontario, Canada, Year: 2025, Photographer: Ajani Charles

When I was the only foreigner at an underground trap party in Shibuya, Tokyo, last summer, I was both amazed and unsurprised to hear nearly every DJ play at least one Drake record.

Still, Drake has not received nearly enough credit for the opportunities he has created for others, and especially for the many Torontonians he has uplifted: artists, producers, filmmakers, designers, dancers, and athletes alike.

The Caribbean Diaspora and Dancehall’s Expansion

Vybz Kartel’s Toronto concerts represented a landmark fusion of Jamaican dancehall and global hip-hop culture.

For the Jamaican diaspora, the shows symbolized a cultural homecoming, reaffirming their deep influence within Toronto’s music scene. For the broader Caribbean community, they elevated regional pride and visibility, proving that Caribbean music belongs on the country’s biggest stages.

For dancehall culture in Canada, these performances marked a turning point, transforming what was once underground community energy into a mainstream, internationally recognized force.

Drake and OVO brought immense cultural and commercial weight to the production, bridging global hip-hop and pop audiences with dancehall, legitimizing Kartel’s influence on an international scale, and ushering in a new era of collaboration between Jamaica’s sound-system legacy and Toronto’s global music identity.

Location: Scotiabank Arena, Toronto, Ontario, Canada, Year: 2025, Photographer: Ajani Charles

Kartel’s performances reinforced how Drake and OVO function as cultural intermediaries, linking Toronto’s creative landscape to global movements with precision, reverence, and ambition.

Behind the Scenes via Project T-Dot

Backstage, alongside my longtime friend and colleague Amol “Mr. Standout” Gupta, I spoke with Mr. Morgan, founder of M3 Entertainment and President of OVO Sound, as well as Noel Cadastre (OVO Noel), one of Drake’s engineers, and documented them and others, such as recording artist Swavy and Jonathan Ramos, VP Global Touring at Live Nation, for Project T-Dot, my nineteen-year-old documentary on Toronto’s hip-hop culture, community, and history.

I also ran into Kim Davis, a gifted recording artist and vocal coach, and her husband Roxx, Drake’s personal trainer and my former high-school classmate Amir Majidi’s business partner.

The highlight of the night came when Kim and Roxx told me how grateful they were to be featured in my solo Project T-Dot art exhibit at Billy Bishop Toronto City Airport, and that their family, friends, and colleagues still send them photos of their prints weekly.

They understand my vision and the immense effort it has taken to document Toronto’s hip-hop culture for nearly two decades.

I was at the concert specifically for Project T-Dot, so reconnecting with Kim, Roxx, and other Torontonians I have documented since December 2006 was meaningful.

Humour, Heritage, and the Deejay Tradition

Talent Manager, Producer, Event Manager, Entrepreneur: Amol Gupta Also Known As Mr. Standout, Recording Artist, Vocal Coach, Entrepreneur: Kim Davis Thornhill Professionally Known As Kim Davis, Personal Trainer, Athletic Coach, Entrepreneur: Alonzo Thornhill Professionally Known As Roxx, Location: Scotiabank Arena, Toronto, Ontario, Canada, Year: 2025, Photographer: Ajani Charles

One of the most entertaining aspects of Kartel’s Toronto run was how he playfully responded to memes and criticism that emerged after the first show, using the second and third shows to address them on stage.

Both Drake and Vybz Kartel have mastered the art of public perception and fan interaction because they remain acutely aware of how the internet engages with their personas and performances.

They understand that in today’s culture, a great musician must also be an entertainer, and both leverage humour, social media, memes, and self-awareness as strategic extensions of their art.

A viral meme about his first performance in Toronto, for instance, shows Kartel dancing on stage to circus music with the caption: “Me watching my $200 dance on stage.”

At his second Toronto concert, Kartel leaned into the joke, dancing and teasing the crowd: “Watch your $200 dance on stage.”

Responding to further chatter about his lack of backup dancers and a lack of dancing on his part, he reminded the audience, with trademark Jamaican wit, that he is “not Chris Brown.”

Many outside Jamaica misunderstand the term “DJ.” In Jamaican culture, a DJ (deejay) is not the person spinning records; it is the vocalist or lyricist who chants, toasts, or raps over a riddim (instrumental).

This tradition, rooted in sound-system culture from the 1950s through the 1970s, shaped modern dancehall, where the DJ’s role is to energize and inspire the crowd to dance, not necessarily to dance themselves.

A Testament to Endurance and Cultural Power

I fully understand why concertgoers who paid $200, $300, and up to $1,500 might have expected greater production or choreography.

But from my perspective, admittedly a highly privileged and biased one, it was nothing short of a miracle that these concerts happened at all, given Kartel’s 13 years of incarceration and his ongoing battle with Graves’ disease, a serious autoimmune condition.

Moreover, he performed for well over an hour without significant breaks, delivering dozens of records; a remarkable feat for someone nearing 50 years old and a powerful testament to his endurance, artistry, vast discography, and unrelenting commitment to his craft.

In the end, Vybz Kartel’s Toronto performances were more than concerts; they were cultural milestones.

Against all odds, he returned to the stage with the same intensity and lyrical precision that made him a legend, reaffirming what many already knew: Vybz Kartel is not only the most prolific dancehall artist of his generation but arguably the most prolific of them all.

His creative resilience and razor-sharp intellect, forged through incarceration, illness, and controversy, reflect the same cleverness and willpower that once enabled him to transcend the impoverished and dangerous streets of Waterford in Portmore, transforming raw struggle into global art worth millions.

Kartel’s evolution from a youth in Kingston’s margins to an international icon embodies the very essence of dancehall and Jamaica itself: defiant, adaptive, and unbreakable.

From a global perspective, the synergy between Kartel and OVO proved that cultural authenticity and commercial excellence not only can coexist but can elevate one another.

The future belongs to those organizations, especially within technology, finance, and media, that recognize and invest in the architects of culture, the visionaries who move people and economies alike.

They are the ones, like Kartel, who continue to inspire movements far beyond the stage.

Rebuilding Lives and Restoring Hope

As Vybz Kartel electrified Toronto with his long-awaited return, Jamaica was simultaneously facing one of its darkest chapters.

Hurricane Melissa, a catastrophic Category 5 storm, killed Jamaican citizens and tourists, devastated the island, displacing families, destroying homes, and crippling livelihoods.

The contrast was sobering: while Kartel’s voice rose over Scotiabank Arena, the very nation that shaped him and gave the world dancehall, reggae, jerk cuisine, patois, hip-hop music and DJ culture, and so much of Toronto’s cultural DNA was reeling from unimaginable loss.

Jamaica has given me, Toronto, Canada, and the world immeasurable gifts through its music, art, language, dance, food, and resilience. Now, it is our turn to give back.

Please consider donating to the Government of Jamaica’s Hurricane Melissa Relief Fund to help rebuild lives and restore hope.