He began his career at the age of twelve leading his own spiritual quartet and singing in the church choir, and performing covers of country and western hits. While he was in high school, Wilson and his family relocated to San Bernardino, California, where he worked three jobs as a mail carrier, a janitor, and an office clerk, in addition to teaching himself to play drums. After graduation he spent four years touring with Johnny Harris and the Statesmen, before joining the U.S. Navy, and singing with an enlisted men's chorus. He also developed his stand-up comedy routine in case he didn't succeed as a singer.