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. Sterling was awarded the Order of Distinction in 1998 in recognition of his contribution to Jamaican music. Sterling's brother is keyboard player Keith Sterling. Lester Sterling the only living foundation member of the original Skatalites band was honored by the USA chapter of JAVAA - "JAVAA USA.ORG" at their first awards ceremony held in Brooklyn New York in April 2013. That event was launched under the distinguished patronage of the consulate general of Jamaica Mr. LaMont, Mr Sterling was given a pioneers awards in the field of music for his contribution since nineteen sixty four and continues to doing it.