Saxophonist and bandleader Bob Chester came from a wealthy family. His step-father was head of General Motor's Fisher Body Works. Chester formed his first orchestra in his hometown of Detroit in 1939. Heavily influenced by Glenn Miller, the group's sound proved unoriginal, and it soon disbanded after initial engagements at the Detroit Athletic Club. Tommy Dorsey took an interest in Chester and invited him to move east and live with him. Dorsey helped Chester organize a new band, which proved more successful. Though it too sounded like Miller at first, later it developed a style of its own, thanks to arrangements by David Rose.
Chester went through a slew of singers. Initial female vocalists included Dolores ''Dodie'' O'Neill and Kathleen Lane. O'Neill married trumpeter Alec Fila and eventually left the band when Fila did. Singer Betty Bradley then joined. Male singers were Gene Howard, Bill Darnell, Joe Harris, Stu Brayton, Hall Stewart, and Bob Haymes, younger brother of actor/vocalist Dick Haymes. Peter Marshall, better known today as the host of the original Hollywood Squares game show, also appeared as a vocalist with Chester. He replaced Howard, who left to join Stan Kenton in 1942. The group recorded on the Bluebird label.
Chester's band broke up around the end of WWII, and he moved back to Detroit. Working as a disc jockey he received so many requests for Dixieland music that he decided to form his own combo. He also formed a new band at the end of the 1940s. Alan Foster was vocalist. Eventually, though, Chester left the music business altogether and entered the automotive industry. Bob Chester died in 1977.