Spending his first years in England, he was exposed to a contrast of sounds which reflected his parents' diverse backgrounds: calypso on the side of his West Indian father, pop and rock and roll from his mother.

Rupee emerged on the local soca scene after being invited to join the then popular Bajan band, Coalishun, along with singers like Terencia Coward and Adrian Clarke in 1997.

"Jump", from his first album, won Rupee repeated Road March titles at carnivals in Barbados, New York City, Miami, Boston and Toronto.

Over the years, Rupee has amassed a number of Party Monarch and Road March titles not only in Barbados, but also at West Indian Carnivals in the United States and Canada.

[4] He has worked with artists such as Rihanna, Shaggy, Thara Prashad, Fay-Ann Lyons, Alison Hinds, Lil' Kim, Daddy Yankee, Wisin & Yandel, Red Rat, Destra Garcia.