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Filmmakers Richard Lerner and Lewis MacAdams explore the unfulfilled promise of Beat Generation icon Jack Kerouac, covering the period from the publication of his notorious novel "On the Road" in 1957 to his alcohol-related death 12 years later. The film features extensive interviews with friends and fellow writers, including the widow of Neal Cassady, who feels that her husband's attempts to live up to the legend of Dean Moriarty, the Kerouac character he inspired, led to his own early death.