Bob Chester

Bob Chester (March 20, 1908 – October 29, 1966) was an American jazz and pop music bandleader and tenor saxophonist.

Chester was born in Detroit, Michigan, United States. He formed his own group in Detroit in the mid-1930s, His only national hit was "With the Wind and the Rain in Your Hair" (b/w "I Walk With Music"; Bluebird 10614), which featured Dolores O'Neill on vocals and went to No. 18 on the chart in April 1940.

Chester's orchestra included trumpeters Alec Fila, Nick Travis, Lou Mucci, and Conrad Gozzo, saxophonists Herbie Steward and Peanuts Hucko, drummer Irv Kluger, and trombonist Bill Harris. His female singers included Dolores O'Neill, Kathleen Lane, and Betty Bradley; among his male singers were Gene Howard, Peter Marshall, Bob Haymes, and Al Stuart.

The orchestra disbanded in the mid-1940s, due in part to the shrinking market for big band sound. After a stint as a disc jockey at WKMH radio, Chester assembled another band for a short time in the early 1950s, but after it failed he retired from music and returned to Detroit, to work for the rest of his life in auto manufacturing.

Bob Chester died in October 1966, at the age of 58.