Credit: Nationa Archieff/ IMS

Watch Bob Dylan and Paul Simon’s sensational duet on ‘The Sound of Silence’ in 1999

It’s always a rare pleasure to see two of the world’s most iconic songwriters share the stage and offer a hand in singing each other’s songs. Even rarer still to see them both complimenting one another. Here, we look back at freewheeling Bob Dylan and Paul Simon’s duet on ‘The Sound of Silence’ from 1999.

Paul Simon may have become used to sharing the stage with another man for many years before he and Dylan toured together in 1999. After all, it was his work as part of Simon & Garfunkel that had largely offered him the chance to take the stage at all—but still, this moment must rank as a special one for all in attendance.

Dylan and his lo-fi performance is a natural fit for Simon. The freewheelin’ Bob Dylan had softened somewhat in his old age and was no longer determined to dominate the stage as before. Now, he was keen that his legacy of some of the best live performances ever known continued in whatever guise those performances could. With that mind, he was always happy to sometimes play second fiddle to the somewhat showier Paul Simon.

The connection between Dylan and Simon is one that goes way back too. Simon & Garfunkel had covered Bob Dylan’s ‘The Times They Are A-Changin’ on their 1964 debut Wednesday Morning, 3 A.M. Covering a song was a favour returned by Dylan some five years later as he took on ‘The Boxer’ for his often maligned covers record Self Portrait.

While their career paths rarely crossed over the years after this, the sharing of songs did establish mutual respect between the singers. It meant that when the duo came around to tour with one another they were keen to ensure that both fans’ needs were met.

Rolling Stone reports that shortly before the tour, Dylan and Simon got together at the latter’s New York apartment with a couple of acoustic guitars and began to strum their way into a setlist. We can only imagine the scene of two of modern music’s finest songwriters pawing over their work together.

It must’ve been a fruitful evening of swapping stories and teaching one another songs, “I consider him one of the preeminent songwriters of our time,” Dylan told USA Today before the tour began. “Every song he does has got a vitality you don’t find everywhere.”

“We were singing folk songs,” Simon said, reflecting the evening of setlist sketching. “Some were obscure, some were better known. It was just two acoustic guitars and it sounded great. But as we got closer to the show, it became apparent what people wanted to hear was us singing each other’s songs. So that’s what we did.”

Beginning at the World Arena in Colorado Springs, Colorado, on June 6th, 1999, it was to be a sensational tour for all those who were lucky enough to see it. As the two huge headliners continued to swap over who opened for each other, the crossover moments between the artists is what really had the crowd going and quickly became the stuff of legend.

It saw Dylan and Simon use their sketched setlist to devastating effect as they dueted on a medley of ‘I Walk The Line’ and ‘Knockin’ On Heaven’s Door’, after ‘Forever Young’ was dropped following the first night. Every so often the duo would throw in retro gems ‘That’ll Be The Day’ and ‘The Wanderer’. However, the standout moment was their duet of Simon’s 1965 hit ‘The Sound of Silence’.

The clip below comes from their performance of the track in Portland, Oregon on June 12th and sees Bob Dylan and Paul Simon showing why they were legends then, back in 1999, and still are to this day.

Listen a timeless moment as Bob Dylan and Paul Simon share the stage to sing ‘The Sound of Silence’.

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