Ramblin' Jack Elliott, a self-styled folk musician, was an important transitional figure between Woody Guthrie and Bob Dylan. This documentary serves as both a chronicle of his colorful life and an attempt by his daughter, director Aiyanna Elliott, to reconnect with her often-absent father. Born Elliott Adnopoz in Brooklyn, Jack ran off as a teenager in 1947 to join a traveling rodeo troupe after seeing them perform in Madison Square Garden. He returned to New York and took up singing, first cowboy songs, then traditional and contemporary folk music. He and Woody Guthrie traveled through the South in the 1950s, learning songs from blues artists such as the Reverend Gary Davis, Elizabeth Cotton, and Jesse Fuller. Elliott remained one of Guthrie's truest friends all through Guthrie's long battle with Huntington's chorea, the congenital nerve disease that killed him in 1967. In 1955, Elliott and the first of his four wives decamped to England, where his reputation was made with fans of the skiffle music craze. He returned to New York in 1961, just as the folk music boom was producing its biggest hero, Bob Dylan, who aped both Guthrie and Elliott in his early recordings. Among the interviewees are Nora and Arlo Guthrie, singers Pete Seeger and Dave Van Ronk, and ex-wives and managers, who all agree on Elliott's carefree attitude toward schedules and money. His almost pathological determination not to conform to any kind of bourgeois lifestyle eventually crippled his chances for wider recognition, though in the mid-'90s, he won a Grammy and a National Medal of the Arts, awarded by President Bill Clinton. The vintage clips are interspersed with Aiyanna Elliott trailing her father around with a camera and microphone, hoping to capture some admission of past mistakes, but as always, Ramblin' Jack Elliott is a tough man to pin down.