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Ready or not?
Skippa
Entertainment, Music
Shereita Grizzle | Observer Staff Reporter  
March 25, 2026

Ready or not?

Skippa at the centre of Sumfest’s headliner debate

A debate has been brewing within Jamaica’s dancehall fraternity following comments by veteran industry figure Josef Bogdanovich regarding whether some of the genre’s hottest young acts are ready to headline major festivals such as Reggae Sumfest.

Bogdanovich, who heads Downsound Entertainment, organisers of the internationally recognised festival, recently addressed the topic while discussing the evolving landscape of dancehall music and the criteria required for artistes to headline major shows.

According to Bogdanovich, while artistes such as Skippa have gained undeniable popularity and viral success, they must still prove themselves worthy of the main spotlight through consistent work.

“They have to earn their way up. What does earn your way up mean? It means to behave properly, to think about others besides yourselves, how to be there [the shows] on time…” Bogdanovich said. “We’ve been around here for a long time. The reason why a Bounty [Killer] and a Beenie [Man] lasted for so long they made better records than anybody else, and they related better to the environment better than anybody else, and they’re still good all over the world.”

Bogdanovich’s remarks prompted a response from Skippa, who expressed that young artistes are always being short-changed when it comes to credibility.

“When we a do good unnu find all sorts a ways fi discredit it,” he said. “Bro, no artiste never just buss and jump up pan a big stage; a phases. We haffi out yah a work ‘til we get it. Keep your show and do your thing, bredda. Di young youth dem ova yah a do we thing too. You nuh haffi book wi.”

With arguments being posited on both sides, the discussion rages on among industry observers. Many argue that Skippa’s rapid rise and dominance on social media platforms already demonstrate his ability to command a large audience, while others argue that headlining Reggae Sumfest carries a legacy that extends far beyond short-term popularity.

Music insiders who chimed in on the debate, told the Jamaica Observer that both arguments hold validity.

According to popular selector DJ Escobar, the virality and popularity of the young entertainers has to be taken into consideration when crafting a line-up for a major local music festival. He also shared that, for an established event like Reggae Sumfest, experience often supersedes ‘what’s trending’, especially when taking into consideration the type of crowd attending the long-standing festival.

“Mi nuh agree fully wid wah Joe say, because over the years, especially recently, a di man dem weh have the viral songs dem a run the place, and Skippa have a good amount a songs weh popular now and a get some attention overseas and have social media gridlock; so, fi me, he would be an asset to the show,” Escobar said.

He also pointed out that, having been established in 1993, there’s a certain level of prestige attached to Reggae Sumfest and as such only artistes of a certain calibre have the necessary pull factor to make the festival a hit.

“Reggae Sumfest is a monster show, and a young act cannot necessarily be the headliner on that kind of show, because in terms of crowd and the whole air around it, it need somebody legendary,” he added. “Right now, Skippa, two or three years into him career, Reggae Sumfest bigger than him as far as being the main act. But young artistes need the platform, so I’m sure he would be an asset on the dancehall night. He would do well so him can get a half hour or 45 minutes and dem cyaah squeeze up him face pan the flyer either.”

Highlighting that not everyone has an eye or even the ear for talent, Isaiah Laing, promoter of Sting, shared that Skippa could be dancehall’s next big star. He shared that, at this stage of his career, all Skippa needs to establish himself worldwide is a global platform.

“Him don’t haffi be a top headliner, but he can definitely be one of the headline acts. What we normally do at Sting is carry the artistes that we see have the talent and we push them. We strategically place them on the posters and we give them the highlight they need. That’s why most of these big-name acts you see now headlining shows are able to do that,” he said. “It’s how you market them. When I hear an artiste and name him, it means him must buss. And I can say Skippa is going to be one of the biggest artiste in dancehall in short order.”

Crediting his Boxing Day show for catapulting the careers of several notable dancehall figures, Laing shared that Sumfest has never really been the platform to push young acts. He said that was largely Sting’s domain.

“Sumfest is not the show that bring young artistes. Sting is the show for that. We normally have a segment dedicated to what these young acts have to say and then, based on response, the following years dem move onto the big stage and get run,” he said. “You have to give the youths a chance to go out there and do them thing. Everybody getting old and the business has to be sustained, so you must carry the young ones and build new headliners.”

“Nobody expects Skippa to headline Sumfest at this stage of his career, but the youth is doing well so he deserves a chance to be one of the main acts,” he continued. “Don’t play down the youths, encourage them.”

The discussion ultimately underscores a broader question facing the genre today: Should traditional benchmarks still determine who headlines Jamaica’s biggest stage, or should the industry adapt to the fast-moving realities of the Digital Age? As anticipation builds for the next staging of Reggae Sumfest, the debate surrounding Skippa’s readiness highlights the ongoing tension between dancehall’s established traditions and the rise of a new generation of stars.

DJ Escobar.

DJ Escobar.

Josef Bogdanovich, organiser of Reggae Sumfest.

Josef Bogdanovich, organiser of Reggae Sumfest.

Isaiah Laing, organiser of StingPhoto: Michael Gordon

Isaiah Laing, organiser of Sting (Photo: Michael Gordon)

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