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In 1927, Calloway joined his older sister, Blanche Calloway, on tour for the popular black musical revue Plantation Days. His sister became an accomplished bandleader before he did, and he often credited her as his inspiration for entering show business. Calloway's mother wanted him to be a lawyer like his father, so once the tour ended he enrolled at Crane College in Chicago, but he was more interested in singing and entertaining.

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