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Looking through the career of Bob Dylan, we can observe the patterns of musical change throughout the twentieth century, relying on the frequent evolution of the folk tradition in a modern context. By examining Dylan’s body of work, we see how an artist of his caliber approaches his craft, weaving new sounds and new songs out of the old musical fabric that has come before. Bob Dylan’s role as a figurehead of popular music for his generation has placed him on a pedestal; what he does in music helps define what it means to be a recording artist, and ultimately what helps define the craft. Dylan’s lyrical techniques of borrowings, as showcased on “Love and Theft” or the re- recordings of traditional folk numbers on Good As I Been to You, have surpassed the expectations of how a song develops overtime, becoming commentary on a new, modern world as well as an expressive of artistic intent. In Dylan’s own words, “I don’t see myself as covering these songs.” It’s an uncovering he’s been looking for. In this essay, I discuss what this uncovering of America’s musical landscape does for the future of how we explore the music of old. I intend to examine how Dylan’s approach to conceptualizing these older songs of varying ages dictates his troubadour character and how as a symbol of America’s culture, Dylan’s career has given us a panorama of American sound.