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On Highway 61 explores the historical context of the significant social dissent that was central to the cultural genesis of the sixties. The book is going to search for the deeper roots of American cultural and musical evolution for the past 150 years by studying what the Western European culture learned from African American culture in a historical progression that reaches from the minstrel era to Bob Dylan. The book begins with America’s first great social critic, Henry David Thoreau, and his fundamental source of social philosophy:---his profound commitment to freedom, to abolitionism and to African-American culture. Continuing with Mark Twain, through whom we can observe the rise of minstrelsy, which he embraced, and his subversive satirical masterpiece Huckleberry Finn.