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He contributed many hit arrangements for the band, including "My Blue Heaven" and "Ain't She Sweet", as well as his original composition " For Dancers Only", which eventually became the band's theme song. In 1933, Oliver joined Jimmie Lunceford's band as a trumpet player, arranger and songwriter. As a composer, one of his most famous songs was " T'ain't What You Do (It's the Way That You Do It)", which he co-wrote with Trummy Young in 1939. Oliver arranged and conducted many songs for Ella Fitzgerald from her Decca years. He also sang with The Sentimentalists on the 1944 recording of his arrangement of "Chicago". In 1941, he sang with Jo Stafford, on his own compositions "Yes Indeed" and "Swingin' on Nothin'". With Tommy Dorsey, he recorded very few vocals. From 1949 to 1951, he recorded more than a dozen with his band. With Lunceford, from 1933 to 1939, he recorded more than two dozen vocals. He continued singing for the next 17 years, making many recordings when he was with Jimmie Lunceford and with his own band. He sang and played trumpet with these bands, becoming known for his "growling" horn playing. Oliver left home at 17 to play with Zack Whyte and his Chocolate Beau Brummels and later with Alphonse Trent.
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His mother was a piano teacher, and his father was a multi-instrumentalist, who demonstrated saxophones at a time when instrument was seldom played other than by marching bands. Sy Oliver was born in Battle Creek, Michigan, United States.