U-Roy's musical career began in 1961 (see 1961 in music) when he began DJing at various sound systems, eventually working with King Tubby. Tubby was then experimenting with his equipment, in the process of inventing dub music. With U-Roy as his most prominent DJ, King Tubby's new sound became extraordinarily popular and U-Roy became a Jamaican celebrity. He recorded Dynamic Fashion Way, his first recording, in 1969 (see 1969 in music). He then worked with Lee Perry, Peter Tosh, Bunny Lee and Lloyd Daley .

In 1970 (see 1970 in music), Jamaican singer John Holt became enamored of U-Roy's technique. Working with Duke Reid, U-Roy's fame grew through a series of singles, including "Wake the Town" and "Wear You to the Ball".

U-Roy's success continued throughout the 1970s and he had become one of the island's biggest stars by the early 1980s, also garnering significant acclaim in the United Kingdom. His latest album is 2000's Serious Matter (see 2000 in music).