In the spring of 1999, two legendary songwriters, Bob Dylan and Paul Simon, found themselves in Simon’s New York City apartment, strumming acoustic guitars and trading folk tunes. The atmosphere was intimate, the sound stripped-down and pure, as they brainstormed ideas for their upcoming co-headlining tour. But as they played, it dawned on them: their fans weren’t there to hear deep cuts or obscure folk songs—they wanted the classics. The setlist quickly shifted to center around each other’s iconic hits, a nod to the legacy both artists had carved into music history.
The tour launched on June 6, 1999, at Colorado Springs’ World Arena, with Simon taking the stage first (they alternated the headline spot each night). Dylan joined him for a series of duets, including a haunting rendition of Simon’s “The Sound of Silence,” a spirited medley of Johnny Cash’s “I Walk The Line” and Bill Monroe’s “Blue Moon of Kentucky,” and Dylan’s own “Forever Young.” But by the second show, “Forever Young” was swapped out for “Knockin’ On Heaven’s Door,” a change that stuck for the rest of the tour. The medley, however, remained fluid, sometimes incorporating Buddy Holly’s “That’ll Be The Day” or Dion’s “The Wanderer,” keeping the performances fresh and unpredictable.
Their musical kinship stretched back decades. In 1964, Simon & Garfunkel had covered Dylan’s “The Times They Are A-Changin’,” and in 1969, Dylan returned the favor by recording Simon’s “The Boxer” for his *Self Portrait* album. Yet, despite these mutual nods of respect, they had never shared a stage until this tour. Reflecting on their collaboration, Dylan offered high praise: “Paul’s one of the preeminent songwriters of our time. There’s a vitality in his work—a spark—that’s rare. You don’t find that just anywhere.”
The tour wasn’t just a meeting of two musical giants; it was a celebration of their shared roots, their enduring influence, and the timeless songs that had defined generations. For fans, it was a once-in-a-lifetime convergence of two voices that had shaped the soundtrack of their lives.
