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Chesnutt is the second son of Bobby Thomas Chesnutt and Norma Jean Nicholas. He learned to love music from his father, who was a singer and record collector. Chesnutt dropped out of school after his sophomore year of high school to begin playing with his father in clubs around Southeast Texas. When he turned 17, his father began to take him to Nashville, Tennessee to begin recording. For the next ten years, Chesnutt began to record on small regional labels while he was the house band for local Beaumont nightclub Cutters.