The Ballad of Ramblin' Jack
2000| 1h 52m| IMDb 6.0
From his unlikely roots as the son of a 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 travelled and sang with Woody Guthrie and became friends and mentored Bob Dylan.
Director: Aiyana Elliott
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Streaming info last checked: 20 Jan 2026