In the early 1940s he moved to Los Angeles, where for one year he was a member of the Chico Marx big band. He appeared in the film "Jammin' the Blues", which featured Lester Young. Soon after, he played in the bands of Charlie Barnet and Artie Shaw. During the day, he worked as a studio musician and at night played jazz in clubs. In 1947 he recorded with Charlie Parker. He worked in Jazz at the Philharmonic and for one year in the early 1950s he was a member of the Oscar Peterson trio. After leaving the trio, he recorded several solo albums for Contemporary. He recorded a series of albums with Ray Brown and Shelly Manne as "The Poll Winners" because the three of them often won polls conducted by "Metronome" and "DownBeat" magazines. He was the guitarist on the album "Julie Is Her Name" (1955) by Julie London, which includes the standard "Cry Me a River," which sold a million copies and demonstrated Kessel's chordal approach to guitar.