A fine bassist, Chubby Jackson is best-known for his association with Woody Herman's first two Herds of the mid-to late '40s, where he functioned not only in the rhythm section but as a sort-of cheerleader whose vocal interjections really pushed the band. Although he started on the clarinet when he was 16, Jackson soon switched to bass and was a professional by the time he was 19, playing with many big bands, including those led by Raymond Scott, Jan Savitt, and Henry Busse.
After touring with Charlie Barnet from 1941 to 1943 (sometimes with Oscar Pettiford as the second bassist), Jackson joined Woody Herman's transitional orchestra and was partly responsible for the group adding many young modernists to the personnel, resulting in the First Herd. Jackson was with Herman during 1943-1946 (appearing on many recordings). After Herman broke up the band, Jackson played with Charlie Ventura's septet (1947) and had his own small group that toured Scandinavia. A second tour with Herman (1948) was followed by a period leading his own big band (1948-1949), more work with Ventura (1951), and a period co-leading a combo with Bill Harris.
Chubby Jackson spent the 1950s as a studio musician, freelancer, and a host of his own children's television show. After periods living in Chicago, Las Vegas, and Los Angeles, he eventually settled in San Diego in semi-retirement, although Jackson occasionally emerged, including for a stint with Lionel Hampton (1978-1979) and with Herman reunion groups