Chesnutt comes from a country music family, his father Bob Chesnutt a singer as well. The younger Chesnutt dropped out of school after his sophomore year in order to tour with his dad and play in clubs around Texas. He went to Nashville with his father when he was 17 and the two worked on recording their own albums under regional labels for 10 years, gathering a nice local fan base, before he finally was signed by MCA Records and became a star.