When the Jamaica Observer named Skippa one of its artistes to watch at the start of 2026, the prediction came with the expectation that the young dancehall artiste’s momentum was worth keeping an eye on. What has followed, however, stretches well beyond even his own expectations. There was the touring, the growing audiences, the songs steadily finding new listeners, and, perhaps most significantly, recognition from one of the music industry’s most established brands — Billboard.
Still, as the artiste himself revealed, 2026 has so far surpassed his wildest imagination. “We had goals around touring and growing the music, but everything kind of surpassed what we had in mind. The amount of shows, the places we’ve been received, the people connecting with the music in places we didn’t necessarily expect, and then Billboard on top of that — it’s been crazy,” he shared.
“We’re grateful for all of it, because you can set goals, but sometimes the reality goes way beyond what you planned for.” Speaking to the Splash, the entertainer said that, although he has been putting in the work, he was taken aback when he was named by Billboard as a Caribbean Rising Star. He admitted that the honour caught him completely off guard and that he had to resist getting swept up in the whirlwind that the moment ushered in. I’m not really the type to overreact, so I was just there trying to take in the moment,” he said.
“Billboard recognising me as a Caribbean Rising Star, in a room with so many people who have been doing this at the highest level, that’s crazy. I’m grateful, for real, and it’s something I’ll always remember.” For an artiste whose career has accelerated considerably in recent years, the recognition represents another marker in a journey that appears to be moving faster than he anticipated. Billboard may have just caught up to Skippa’s burgeoning career, but the proverbial writing was on the wall since the latter part of last year.
By December 2025, YouTube year-end statistics showed that the entertainer had already emerged as Jamaica’s third-most-viewed artiste on the platform, behind Chronic Law and Vybz Kartel, with approximately 79.9 million views. His numbers remained consistent in 2026, with the artiste repeatedly placing multiple songs among Jamaica’s most-streamed records.
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