Born in Muskogee, Oklahoma, Kessel took on Christian's mantle in the mid 1940s and carried it through to the late 1980s. An innovative guitarist, he followed and developed Charlie Christian's swing style of playing, developing the harmonic possibilities of the instrument in a way that clearly showed a guitar player could do anything a piano player could do, and sometimes better.

Kessel got his first guitar at age twelve and was playing gigs with all-black bands two years later. At sixteen he met and jammed with Charlie Christian, whose music he knew from recordings and radio broadcasts with Benny Goodman. A year later he left for Los Angeles to make it as a musician.

He got a job in Chico Marx's band, and in the mid-1940s he was featured with Charlie Parker and Lester Young. He was also featured with Lionel Hampton in the Jazz at the Philharmonic concerts. By 1947, he had worked with a number of big bands, including Benny Goodman's and Artie Shaw's. That same year he went into the studio with Charlie Parker, and the results were some classic bebop recordings that established Kessel as an accomplished and confident musician.

He continued to play jazz and tour until 1992, when he suffered a stroke that left him unable to play any more. He continued to teach, however, and eventually regained his ability to speak and move.

In 1934, Gibson introduced the large-bodied arch-top Super 400, designed to give more volume.

In 1952, Kessel joined the Oscar Peterson Trio for a Jazz at the Philharmonic tour that visited fourteen countries. He continued to record with Peterson and a score of other major jazz names. In the late 1950s and the 1960s, he became a major figure in the Los Angeles recording industry. His 1955 Trio record Cry Me a River, featuring singer Julie London, is a classic of its type. He also recorded a series of records called The Poll Winners with bass player Ray Brown and drummer Shelley Mann. The records were so-called because he and his partners consistently won jazz polls in Down Beat, Esquire, Playboy, Metronome, and Melody Maker magazines.