From his unlikely roots as the son of a Jewish doctor in brooklyn, to his ongoing wanderings 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 the age of fifteen, he traveled and sang with Woody Guthrie and became friend and mentor to Bob Dylan. His music helped ignite a folk revolution in the '60s and has influenced some of the most popular musicians and performers of our day. Jack's daughter Aiyana had originally wanted to document the great rambler in action and bring his story to light. However, when she hit the road with him, the focus of the story turned from the roving cowboy's life on the road to the daughter's search for a dad who was rarely at home. Shot over the course of two years, the film skillfully weaves stella performances, contemporary verite, candid interviews and a wealth of archival material including never-before-seen home movie from the Guthrie family's private collection resulting in a film that takes us beyond the legend and into the psyche of the man.