No One Expected It—Paul Simon Was Gently Singing “The Sound of Silence” When Suddenly Bob Dylan Stepped Out of the Shadows and Joined In, Creating a Haunting, Once-in-a-Lifetime Duet That Froze the Room, Shattered Expectations, and Made Everyone Feel Like They Were Witnessing Music History Being Rewritten Right Before Their Eyes

  • byJasmin
  • November 10, 2025
  • 1 minute read
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Before their 1999 co-headlining tour, Bob Dylan and Paul Simon met at Simon’s New York apartment to brainstorm duet ideas. They played folk songs on acoustic guitars, enjoying the raw, simple sound. However, they soon realized fans wanted to hear them perform each other’s hits, so they built their setlist around that.

The tour kicked off on June 6, 1999, at the World Arena in Colorado Springs, Colorado. Simon opened the show (they took turns headlining each night), and Dylan joined him for duets on “The Sound of Silence,” a medley of “I Walk The Line” and “Blue Moon of Kentucky,” and “Forever Young.” By the second show, they swapped “Forever Young” for “Knockin’ On Heaven’s Door” and kept that lineup for the rest of the tour, occasionally changing the medley to include “That’ll Be The Day” or “The Wanderer.”

Flashback: Bob Dylan and Paul Simon Duet on 'The Sound of Silence'

Their musical connection went back decades. In 1964, Simon and Garfunkel covered Dylan’s “The Times They Are-A Changin’,” and in 1969, Dylan covered Simon’s “The Boxer” on his album Self Portrait. Despite this, they didn’t share the stage until the 1999 tour. Reflecting on the collaboration, Dylan said, “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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