He began his musical career as a trumpet player for the Val Bennett Band in 1957 and went on to play with Bryon Lee and the Dragonaries. He soon picked up the Saxophone and in 1964 joined other musicians to form The Skatalites.
After the Skatalites disbanded for the first time in 1965, Sterling went on to record with producer “Sir” Clancy Collins. Here he kept the traditional “Jamaican Ska” flowing that was started with The Skatalites. Sterling recorded such hits as, “Can’t Sit Down” and his version of “Afrikkan Beat.”
Sterling rejoined the Skatalites when the reformed in 1984 for Reggae Sunsplash concert and has been touring and recording with them ever since.
Lester Sterling was awarded the Order of Distinction on November 16, 1998 for his distinguish contribution to Jamaica’s Music.