`A native of Kansas City, Missouri, he studied violin, learned how to play blues on the piano from Pete Johnson, and received saxophone lessons from Budd Johnson. He played with Lester Young in the Young Family Band. He recorded with Blanche Calloway and became a member of the Bennie Moten Orchestra with Count Basie, Hot Lips Page, and Walter Page. During the 1930s, he played in bands led by Willie Bryant, Benny Carter, Cab Calloway, Fletcher Henderson, Andy Kirk, and Teddy Wilson.

With Ellington Webster was a soloist with the Duke Ellington Orchestra starting in 1940, appearing on "Cotton Tail". He considered Johnny Hodges, an alto saxophonist in the Ellington orchestra, a major influence on his playing.[5] Gunther Schuller wrote in 1989 that Hodges influence pushed him away from his original inspiration, Coleman Hawkins. Webster became close to Jimmy Blanton and Billy Strayhorn, the other two newcomers to Ellington's orbit.

Webster's personality, however, proved difficult for most members of the orchestra and for Ellington. It was not possible, according to Mercer Ellington, for his father and the saxophonist to be in the same room without an argument developing. Webster cried when he heard Blanton had died, but as baritone player Harry Carney recalled, "After he had a drink or two, he'd change". Webster left the band in 1943. Reportedly, he cut one of Ellington's sports jackets with a razor as one of his last acts as a member of the Ellington orchestra. Clark Terry said the departure was because Webster slapped Ellington.

Later American career Webster worked on 52nd Street in New York City, where he recorded frequently as a leader and sideman. During this time he worked with Raymond Scott, John Kirby, Bill DeArango, Sid Catlett, Jay McShann, and Jimmy Witherspoon. For a few months in 1948, he returned briefly to Ellington's orchestra.

In 1953, he recorded The Consummate Artistry of Ben Webster (now known as King of the Tenors) with pianist Oscar Peterson, who would be an important collaborator with Webster throughout the decade in his recordings for the various labels of Norman Granz. Along with Peterson, trumpeter Harry "Sweets" Edison and others, he was touring and recording with Granz's Jazz at the Philharmonic package. In 1956, he recorded an album with pianist Art Tatum, supported by bassist Red Callender and drummer Bill Douglass. Coleman Hawkins Encounters Ben Webster with fellow tenor saxophonist Coleman Hawkins was recorded on December 16, 1957, along with Peterson, Herb Ellis (guitar), Ray Brown (bass), and Alvin Stoller (drums). The Hawkins and Webster recording saw the coming together of two giants of the tenor saxophone, who had first met back in Kansas City.

In the late 1950s, he formed a quintet with Gerry Mulligan and played frequently at a club in Los Angeles called Renaissance. It was there that the Webster-Mulligan group backed up blues singer Jimmy Witherspoon on an album recorded live for the Hi-Fi Jazz label. That same year, 1959, the quintet, with pianist Jimmy Rowles, bassist Leroy Vinnegar, and drummer Mel Lewis, also recorded Gerry Mulligan Meets Ben Webster for Verve Records.