Two undoubted legends of their field, Paul Simon and Bob Dylan are two rare talents. Some of the most gifted songwriters America has ever produced, the duo even shared a joint tour in 1999. It produced some notable moments, including this duet on Dylan’s classic ‘Knockin’ On Heaven’s Door’.
Below you can revisit that special moment with the bootlegged audio, ah, don’t you just love folkies. Beginning at the World Arena in Colorado Springs, Colorado, it was to be a sensational tour for all those who saw it.
As the two headliners continued to swap over who opened for each other, at the performance below, at Mountain View, CA Shoreline Amphitheater n June 19th in 1999 Simon opened and welcomed Dylan to the stage.
Rolling Stone reports that shortly before the exciting 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. 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.”
Dylan and Simon use their sketched setlist to devastating effect as they dueted on a medley of ‘I Walk The Line’ as well as ‘The Sound of Silence’, 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’. But a standout moment was their duet of ‘Knockin’ On Heaven’s Door’.
It’s arguably one of Dylan’s most famous songs and was given extra weight with the inclusion of Simon, as the singer’s honest oval rings true. It’s something that Simon noted in a recent interview where he shared his displeasure at often being considered Dylan’s subordinate.
“I usually come in second to Dylan, and I don’t like coming in second,” he said. “In the beginning, when we were first signed to Columbia, I really admired Dylan‘s work. ‘The Sound of Silence’ wouldn’t have been written if it weren’t for Dylan. But I left that feeling around The Graduate and ‘Mrs Robinson’. They weren’t folky any more.”
“One of my deficiencies is my voice sounds sincere. I’ve tried to sound ironic. I don’t. I can’t. Dylan, everything he sings has two meanings. He’s telling you the truth and making fun of you at the same time. I sound sincere every time.”
It’s that sincerity that balances Dylan’s nonchalance at remembering the tune or even the lyrics at points. It shouldn’t work but it certainly does and the two counterpoints move in tandem to deliver a bone-chilling performance. Below you can listen to Paul Simon and Bob Dylan dueting on the classic, ‘Knockin’ on Heaven’s Door’ from 1999.