Bobby Caldwell was likely destined to be an entertainer. The son of Bob and R.H. Caldwell, longtime singers and dancers who were also the hosts of an early TV variety show, Suppertime, he was raised in a world surrounded by great entertainers and classic music. Exposed by his parents to opera, jazz, swing, blues, folk and other popular forms of music, he developed an early appreciation for the different architectures of various types of music — an appreciation that would later help him to move from soul to adult contemporary to smooth jazz to big band sounds during his career.