From his unlikely roots as the son of Brooklyn doctor, to his ongoing ramblings as the last of the singing cowboys, Ramblin' Jack has packed so many adventures into his life that he seems more myth than man. After running away to join the rodeo at fifteen, he traveled and sang with Woody Guthrie and became friend and mentor Bob Dylan. His music helped ignite a folk revolution and has influenced some of the most popular musicians and performers of our day. Jack's daughter Aiyana wanted to capture the great rambler in action and bring his story to light. But when she hit the road with him the focus of the story shifted from the roving cowboy's life on the road to the search for a father who was rarely at home. Shot over the course of two years, the film skillfully weaves stellar performances, contemporary verite, candid interviews and a wealth of archival material, resulting in a film that takes us beyond then legend and into the psyche of the man.