Sy Oliver's melodic yet sophisticated arrangements helped define the Jimmy Lunceford sound in the 1930s and modernized Tommy Dorsey's band in the '40s. A fine trumpeter (excellent with a mute) and a likable vocalist, Oliver made his recording debut with Zack Whyte's Chocolate Beau Brummels in the late '20s and also worked with Alphonse Trent. Joining Lunceford in 1933, Oliver was responsible for such memorable charts as "My Blue Heaven," "Ain't She Sweet," "Organ Grinder's Swing," and "'Tain't What You Do," among many others. It was a major blow to Lunceford when Oliver jumped at the chance to make a lot more money arranging and occasionally singing for Tommy Dorsey. The hiring of Sy Oliver was a major help for T.D. in getting Buddy Rich to join his band. Oliver's arrangement of "On the Sunny Side of the Street" was his biggest hit for Dorsey. After a brief attempt at leading his own orchestra in 1946, Oliver became a freelance arranger and producer for the remainder of his long career. As late as 1975-1980, he was regularly leading a band but Sy Oliver will always be best known for his classic Lunceford charts.
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