The legendary Hi De Ho man was a energetic showman, gifted singer, talented actor and trendsetting fashion plate. A truly larger than life figure in American pop culture, immortalized in cartoons and caricatures, Calloway also led one of the greatest bands of the Swing Era. Consistently ranked among the top bands of the 1930s and 1940s, Calloway's orchestra entertained millions during its heyday, and the bandleader himself continued thrilling audiences up until the time of his death.
Born in Rochester, New York, Cab grew up in Baltimore. He studied music and voice as a youth, singing at local speakeasies when he could. Cab also excelled in sports. During his senior year in high school, he played for the Baltimore Athenians of the Negro Professional Basketball League. Torn between sports and music, he finally chose the latter. His mother, however, wanted him to follow his father's footsteps and become a lawyer. With that goal, Cab moved to Chicago to attend Crane College.
His older sister Blanche was already in Chicago, singing and dancing professionally. She helped Cab get a job with her in the musical review Plantation Days, when the show closed in 1927 Cab found a job singing at the Dreamland Cafe. In 1928 he went to work as the emcee of the Sunset Cafe, which also featured a house band called Marion Hardy's Alabamians. One day, during rehearsal, he decided to do a number with the band. They liked him so much they made him their leader. Cab dropped out of college to pursue a career as entertainer.