Joan Baez
Probably one of his more tumultuous relationships, and definitely the most important. Joan Baez was a superstar folk singer with a wide reputation long before Dylan was, and it was her stamp of approval that helped push him into the spotlight. Their brief affair saw them perform together at the 1963 civil rights March on Washington, and, though he seemed to string her along for some time, he is rumored to have written the songs "Visions of Johanna" and "She Belongs To Me" about her. In turn, she recorded a bittersweet memorial to their love with "Diamonds and Rust" in 1975.
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