IWaata Inks Management Deal With Reynolds Entertainment Agency, Plots Caribbean and UK Tours

Dancehall artiste Jason 'IWaata' Bailey has formalised a new chapter in his career, signing a management agreement with Tameka Reynolds of Reynolds Entertainment Agency. Known for a delivery that swings between gritty intensity and hook-driven appeal, the artiste will now have the agency oversee every facet of his professional output.

"The move reflects a step toward more structured management as IWaata develops his brand both locally and internationally," Reynolds said, indicating that the agency would handle the full scope of his career.

While his catalogue sits firmly within the modern dancehall mould, IWaata is candid about his love for the genre's 1990s and 2000s era, and traces of that golden-age influence surface regularly in his work. He first dabbled in music as a pupil at Mona Primary School, where he played the kette drums, and according to his biography cut his first official record in 2007 at the start of high school. He held back from a full-time pursuit until completing school in 2011, after which he relocated to Portmore to live with an aunt and began studio sessions with members of a group called NTP.

Family, particularly his mother, remains central to the artiste, who was raised alongside his grandmother and a brother. "My mom is my everything. My mother is very important inna mi life. I used to help her sell a Half-Way Tree. Those things give you the drive to go for what you want," he said.

His discography features tracks such as Clip Tall, Likkle London, Bad Inna Bed, Bout Yah, Cut Off Jeans and Tun di Ada Way, the latter approaching seven million views on YouTube. By keeping the spotlight on craft, he has earned a reputation as one of dancehall's more flexible vocalists.

Last Saturday, 5 Questions With ... caught up with the artiste during ONErpm's 'Thank You' event at The Courtyard at Ranny Williams Centre on Hope Road, St Andrew.

1. When did you start taking an interest in music?

"I'm from Kintyre and there was like a musical environment, a whole heap a artiste forward from roun' deh. But my interest in music really started from primary school where I used to play drums. Then, when I attended Papine High, I started write songs from first form. I used to play football and dem tings deh, 'cause yuh done know wi grow rough."

2. In Jamaica, we refer to tears as 'eye water'. How did you get your name?

"I used to have a tree in my yard and, whenever it blossomed, it irritated my eyes ... dem get red like blood so my grandfather used to say 'eye wata'. So, growing into music, I was searching for a name and I decided to take the nickname my grandfather gave me. I changed the spelling to IWaata and the rest, as they say, is history."

3. What have you been up to recently?

"Well, we in and out of the country. We drop a new album last year August and we drop a new EP in February, a reggae EP, and we have a song that a gwaan now. The song name Join Up, the album name Underrated and it has 18 tracks. The EP name Words Not Enough and it has seven songs. That's how it go, we always a work ... hits after hits."

4. You are a huge fan of '90s dancehall and credit Aidonia as a major influence in your career. Was music the right choice, and are you enjoying this journey?

"Aidonia was my idol, that's how I get my sound because I always like how him handle beats and stage. Music is the right choice. I never choose music, it chose me. From a tender age me a beat drum and now I can play other instruments and even be my own engineer. I dwell inna the music deep. I get encouragement 1000 per cent from my family. They are musicians too, dem just never get the break that I got. Wherever I go, I represent fully for dancehall. Just like how we get invited from atONErpm directly and we haffi show up. It is important for me to represent in these spaces. A nuh carpentry we do, we do music, and this is a music function where music players come and socialise."

5. In terms of live performances, what do you have lined up?

"I have a Caribbean tour and an England tour coming up this year. But, in terms of shows throughout the year, I have a huge fan base in the US, so the shows from over there are consistent."

BRAWTA — Name one thing that you are grateful for since the start of 2026.

"Well, every year me get a hit song, and this year mi get one already – Join Up. And mi haffi big up Fada God, because it coulda worse. Mi can tek care a mi family every day and every year and that is the important part ... . Also, I have a message for up-and-coming artistes: Stay focused, believe inna God and stick to the plan."