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Webster began his musical life whilst still in Elementary school, studying violin and teaching himself piano. After a short time playing for silent film, Webster moved to Amarillo, Texas, where he was taught rudimentary saxophone by Budd Johnson. In 1930 he left Amarillo to perform with the Gene Coy's Happy Black Aces, and would be Coy who bought Webster his first tenor, as he later explained: "I couldn't express myself on alto. The tenor had a bigger sound." A major milestone during this period of his career came from Webster's association with Duke Ellington, having first appeared with the bandleader as early as 1935, and would become a full time member of his orchestra by 1940. Webster was often quoted as saying that Johnny Hodges, Ellington's alto saxophonist, has a major impact on his own playing style, and his contributions can be heard on such famous recordings as 'Cotton Tail,' his signature tune, and 'All Too Soon.' In fact, alongside bassist Jimmy Blanton, Webster's contributions to Ellington's group were considered of such important that the orchestra was referred to as The Blanton-Webster Band for a time. However, Webster would eventually leave in early August 1943, with a physical confrontation with Ellington. Following his departure, Webster spent much of the 1940s playing as both leader and sideman. In 1953 he recorded his first full LP as leader, King of the Tenors (Verve), which featured the playing of pianist Oscar Peterson who would become one of Webster's key collaborators throughout the rest of the decade. What was to follow was perhaps the most fruitful period of Webster's recording career, releasing six albums as bandleader between 1955 and early 1959. These would include classic Soulville , considered by many to be his finest and most characteristic work, and Coleman Hawkins Encounters Ben Webster, not only seeing Webster once again collaborate with Oscar Peterson but also one of his initial saxophone influences.

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