The tour officially began on June 6, 1999, at the World Arena in Colorado Springs, Colorado. Paul Simon opened the first show (the two artists alternated headlining duties throughout the tour), and Bob Dylan joined him for several memorable duets, including “The Sound of Silence,” a medley of “I Walk the Line” and “Blue Moon of Kentucky,” and “Forever Young.” By the second performance, “Forever Young” was replaced with “Knockin’ On Heaven’s Door,” a change that remained consistent for the rest of the tour. From time to time, the medley evolved to feature classics such as “That’ll Be the Day” or “The Wanderer.”

Their musical connection had roots stretching back decades. In 1964, Simon & Garfunkel recorded a rendition of Dylan’s “The Times They Are A-Changin’,” and in 1969, Dylan offered his own interpretation of Simon’s “The Boxer” on his album Self Portrait. Yet despite this history, the two icons didn’t share a stage until their 1999 tour. Reflecting on their collaboration, Dylan remarked, “I consider him one of the preeminent songwriters of our time. Every song he does has a vitality you don’t find everywhere.”

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