 His first session for Federal produced "K. C. Loving", written by Jerry Leiber and Mike Stoller and later re-recorded by Wilbert Harrison as "Kansas City".By 1957 Littlefield had moved to northern California and continued to record for Don Barksdale's Rhythm label in San Francisco, for which he produced the single "Ruby, Ruby".Littlefield's recording and his subsequent releases were not successful, but he remained a popular performer in clubs in the San Francisco area.