Vestine's love of music and the blues in particular was fostered at an early age when he accompanied his father on canvasses of black neighborhoods for old recordings. Like his father, Henry became an avid collector, eventually owning tens of thousands of recordings of blues, hillbilly, country, and Cajun music. At Henry’s urging, his father also used to take him to blues shows at which he and Henry were often the only white people present. Later Henry was instrumental in the "rediscovery" of Skip James and other Delta musicians.