Some artists break through with their very first single; others go their entire careers unheard. Trinidad Killa, who’s been in the music industry for a quarter-century now, got his long-overdue break nine years ago, but a recent career-shifting collaboration with Billboard’sNo. 1 Greatest Female Rapper of All Time sent an entirely new – and infinitely stronger – wave of momentum his way.

Hailing from Arima in Trinidad & Tobago and currently residing in Flatbush, Brooklyn, Killa has always followed wherever his creative inclinations led him. In the early-mid ‘10s, Killa frequently entered music competitions – from Soca Star and Digicel Rising Stars to more local street showdowns. In those clashes, Killa’s near-perfect victory streak earned him his nickname, and he continued honing those skills on Basilon Street, the area of the island that would give way to a popular subgenre of Trinbagonian dancehall called “zess.”

As one of the self-proclaimed pioneers of zess, Killa scored one of the style’s earliest hits with 2019’s “Gun Man in Yuh Hole,” which he’s since parlayed into his first three nominations at the Caribbean Music Awards. As exclusively revealed by Billboard, Killa earned nods for zess-steam artist of the year, best new soca artist and the soca impact award.