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.

Dancehall artiste Skippa.

“Honestly, I was taken aback. 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.

Still, he remains humble, crediting his chart success to his loyal fan base rather than to a secret creative formula.

“I wouldn’t say I figured out some formula, because I think what really sets my work apart is that people just relate to me. I’m being myself and making music from my own experience and perspective, and people see themselves in that,” he said.

That connection, he believes, matters more than the numbers themselves — or any ‘trending list’ he may or may not find himself on.

“I don’t chase whatever trend is happening just because it’s working for somebody else. I just try to make good music and stay authentic, and the people decide what they want to run with,” he said.

It is a philosophy that has become increasingly important as the numbers have grown.

For Skippa, there is a difference between having a hit song and building something that can last.

“Consistency, for sure. I think that’s one of the biggest things,” he said. “You can have one song that catches fire, but building a career is different. You have to keep showing up, keep making music, keep performing, keep connecting with the people, and keep growing.”

With that mindset, the entertainer shared that he is looking at his recent success as motivation to go even further, rather than being tricked into believing he has somehow arrived.

“To come into this space and, in such a short time, see my name alongside artistes who have been doing this for years, that’s a big thing. It’s definitely something I’m grateful for and amazed by,” he said. “But I don’t look at it like I’ve arrived and that’s it. It just makes me appreciate the journey even more and motivates me to keep working.”

The entertainer sought to acknowledge the machinery working for his good behind the scenes. Naming his manager, Cristina; engineer, producer and DJ Travis; Chargie Records; Solitary Muzic; and Bankroller, among others, as people who have contributed to his progress, Skippa expressed that, “Everybody played their part, so when I’m on that stage accepting something like Billboard Rising Star, I know it’s not just about me.”

The prediction made by the Observer at the beginning of the year has taken on a life of its own. Having lived up to the ‘one to watch’ status, Skippa is now ready to take things to the next level as he cements his place among dancehall’s best.