20 Years Ago Bob Dylan and Paul Simon Were On Tour Together and Shared a Stage Here in Duluth

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Photo by the author. Part of a tabloid spread about the upcoming Dylan-Simon concert, July 3, 1999.

Every living artist of influence has lived through plenty of July Threes, but in seeing the stories on about Brian Jones and Jim Morrison, who each died on this date in 1969 and 1971, respectively, it brought to mind the July 3 of 1999 when Bob Dylan returned to his home town of Duluth for the second time within a year, performing with Paul Simon and his band 20 years ago yesterday.

I dont recall any reference at the time to that being the 30th anniversary of Brian Jones’ death, which is now 50 years. What I do recall is how muddy Duluth’s Bayfront Park was after the hard rain, and how much fun some people had listening to the music while slip-slidin’ away. (O.K. the muck wasn’t fun for all.)

Paul Simon’s stature as a songwriter far exceeds his height as a man. His 13 song setlist was followed by a seven song encore, the last five being performed with Bob Dylan, who never looks tall but definitely made one realize how short Simon was.

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Public domain.

On July 3 (yesterday) I picked up Robert Hilburn’s authorized bio of Paul Simon and was immediately drawn in to the story of Paul Simon’s life beginning with his ambition to be a baseball player, a passion many youths shared at that time. Despite the shortcoming of his size, he excelled sufficiently to be a Queens all-star in high school. But lacking the “growth spurt” he’d hoped for as a teen, there was no way he could advance beyond the dream stages of this first passion.

Music, which had always been part of his life (his father performed for a living), moved in to fill the gap. And even though writing songs took more effort for Simon than for Lennon and McCartney for example, the work he produced became part of the soundtrack for our generation, expressing our hopes, anxieties and struggle to find a place for ourselves in a turbulent world.

You’d think that being from New York would have given Paul Simon an edge in the influential music world there, but Hilburn’s account tells how Simon’s formative years included trips to England and busking in Paris before really getting traction at Columbia Records, accompanied by Art Garfunkel.

Bob Dylan shows up in numerous sections of the book. Columbia producer Tom Wilson was one of the few execs there who supported John Hammond’s early enthusiasm for Dylan. Wilson saw Paul Simon’s potential as well. Similarly both singer/songwriters were performing at the same places in Greenwich Village. When Dylan’s Freewheelin’ was released Paul Simon was duly impressed, especially by Hard Rain’s A-Gonna Fall and the “enchanting love song that Simon liked,” Girl from the North Country.

The message that came through for Simon was just what he needed at the time. “Simon found in Dylan’s writing a natural way to blend his love of music and everything he’d learned in college about writing and the social order.” As he later acknowledged in interviews, he was liberated from having to produce pop hits, and could create music that appealed to him more thoughtfully. This is how Simon & Garfunkel’s albums became a part of so many of our lives at that time.

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Photo by the author.

When Paul Simon and his ensemble joined Bob Dylan on the stage here in 1999, the song selections were especially interesting. Dylan’s setlist was heavily weighted to his Sixties songs in which he was a prophet for our times. Two songs were shared from Blood on the Tracks and two more from Time Out of Mind. Until the encore, Simon’s set only featured two songs from his Sixties recordings with Art Garfunkel. Instead he featured his solo career and international influences, which most vividly emerged on his fabulous Graceland album.

Despite the sloppy conditions it was a night to remember.

Related Links

Bob Dylan Setlist from July 3, 1999 in Bayfront Park, Duluth

This story about the death of Brian Jones appeared on Expecting Rain this morning. A daughter of Jones is claiming her father was murdered, an accusation that former crime reporter Anthony Scaduto alleged in his pointed bio Jagger: Everybody’s Lucifer.

The hard-boiled Scaduto had published a bio of Bob Dylan two years previous.

To catch the flavor of this concert tour with Simon and Dylan, here’s a New York Times review of their concert a few weeks later in Madison Square Garden. “The Sound of Simon and Dylan.” If you don’t have time to read the story, here are two excerpts.

The two have much in common. Born in 1941, they are among the best and most expansive songwriters of their time, each with one hand firmly clasping the political and intellectual zeitgeist; they were both lifted out of the 60’s Greenwich Village folk scene by Columbia Records and they are constantly reinventing their sound when their audiences least expect it. And Mr. Simon covered Mr. Dylan’s ‘’Times They Are A-Changin’ ‘’ on the first Simon and Garfunkel album, while Mr. Dylan remade Mr. Simon’s ‘’Boxer’’ on his ‘’Self-Portrait.’’

And two paragraphs later:
Where the cryptic Mr. Dylan is a tangled, dusty back road on which it is impossible to see more than a few feet ahead, the more transparent Mr. Simon is as obvious and scenic as a parkway. And though singing harmony is second nature to Mr. Simon, trying to harmonize with Mr. Dylan is like trying to catch a fly with chopsticks. As a result, ‘’The Sound of Silence’’ turned from a haunting ballad to a cacophonous prophecy punctuated with a harmonica solo while ‘’Heaven’s Door’’ sounded slightly better when the two took turns singing.

Meantime, life goes on… and so is Bob’s Never Ending Tour, with shows in Germany, England and Ireland the next two weeks. You can read the reviews and other news at

Originally published earlier today at

An avid reader who writes about arts, culture, literature & other life obsessions. @ennyman3 Look for my books on Amazon

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