Background
Two accounts have been proposed regarding the song's inspiration, neither of them conclusive. In one, "Bob Dylan's Dream" recalls the times Dylan had spent in Greenwich Village with comedian Hugh Romney and their friends during the early 1960s. Romney, later to become Wavy Gravy of Woodstock and Merry Pranksters fame, lived above The Gaslight Cafe on MacDougal Street, where he worked as entertainment director. The two first met at the Gaslight in the spring of 1961. Dylan approached Romney about the possibility of performing and began appearing regularly at the Gaslight's hootennanies. Within a few months, he debuted at the Gaslight as a featured act.
Dylan frequently hung out upstairs in Romney's apartment and wrote one of his most significant songs there, "A Hard Rain's a-Gonna Fall", in August 1962 . The next winter, in late January or early February 1963, he wrote "Bob Dylan's Dream" possibly as a nostalgic remembrance of his early days in the Village when his life was less complex.
However, according to biographer and critic Robert Shelton, the song concerns the lost innocence of his adolescence in Hibbing, Minnesota. John Bucklen, one of Dylan's closest friends in Hibbing in the mid-1950s, told Shelton he and Dylan used to venture out to his sister's house, where they would play guitar and sing verses. "When I heard the song 'Bob Dylan's Dream'," he said, "I couldn't help but think that some of the sessions we had at my sister's house were part of that 'Dream.'"
Read more about this topic: Bob Dylan's Dream
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