He started out playing in local bars in 1953, with fellow Arkansan Levon Helm joining his band five years later. In 1959, he was signed by Roulette Records, leading to minor hits Forty Days and Mary Lou and an appearance on American Bandstand. Rick Danko, Garth Hudson, Richard Manuel and Robbie Robertson eventually joined him on the bar and club circuit in Canada. They later left together for the US and became the Band.