Like many Jamaican musicians of his generation, Sterling attended the Alpha Boys School. Originally a trumpeter, he is predominantly known as a player of alto saxophone. He was a member of the Jamaica Military Band in the 1950s and played trumpet in Val Bennett's band in 1957. In the late 1950s and early 1960s, Sterling played regularly as a studio musician, along with most of the future Skatalites members, in bands such as Clue J & His Blues Blasters.
Sterling is a founding member of The Skatalites (playing alto saxophone), one of only two (the other is Doreen Shaffer) still alive. After The Skatalites originally disbanded in 1965, Sterling played with Byron Lee & the Dragonaires and recorded several solo singles for the London-based producer "Sir" Clancy Collins. His debut solo album, Bangarang, was released on Pama Records in 1969. Sterling rejoined the Skatalites when they reformed in 1975. The band have continued on and off with a varying line-up since, and Sterling is the only founding member still with the band.