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Flashback: Bob Dylan & The Band Headline The ‘Isle Of Wight Festival’

By Music News Aug 30, 2022 | 7:00 PM

It was 53 years ago tonight (August 31st, 1969) that Bob Dylan made his first full-length concert appearance in three years at the Isle Of Wight Festival. Dylan's hour-long set with the Band closed the three-day festival, which also featured the Who, Richie Havens, the Moody Blues, Joe Cocker, and a solo set by the Band.

After very little rehearsal, Dylan and the Band took the stage in front of a crowd of an estimated 200,000 people — including John Lennon, George Harrison, and Ringo Starr. In front of a battery of microphones, a bearded Dylan, clad in a white suit and playing a large Gibson hollow-bodied acoustic guitar, gave an hour-long, spirited performance of 16 songs, spanning his then eight-year career.

The Band's late drummer Levon Helm recalled the show to author Clinton Heylin for his Dylan biography Behind The Shades, saying, “I would've like to have gotten carried away. Bob had an extra list of songs with eight or ten different titles with question marks by them. . . But it seemed like the festival was three days old by then; and so, if everybody else is ready to go home, let's all go.”

During his August 17th, 1969 press conference prior to his prior to his return to the stage at the Isle of Wight Festival, Bob Dylan was pressed as to his stance on the drug scene: “I don't have any of those views. I wish I did, 'be glad to share them with you, but I. . . I think everyone should do their own life. Y'know?”

Robbie Roberston, who along with the Band, had begun performing with Dylan in 1965 when they were still known as the Hawks. He recalled that Dylan was always about moving his art forward — even if early on his fans couldn't understand or accept his musical changes: “Bob was somebody who was rewriting the book on music. He was taking his folk influences, applying them to rock n' roll, and it was. . . it had more depth. It was smarter, it was more adventurous, it was breaking some rules. To be around and to be part of that whole thing — alongside of the booing and everything — that was quite inspirational.”

Columbia Records recorded the shows on a portable eight-track machine, and four of the songs, “She Belongs To Me,” “Minstrel Boy,” “Like A Rolling Stone,” and “The Mighty Quinn,” were included on Dylan's 1970 Self Portrait album.

Over the years, the concert has been widely bootlegged from several sources, including the sound from local film crews, crude recordings from audience members, and even a low-generation dub from the Columbia master tape.

Dylan has gone on record as saying that when he found out about the Woodstock festival taking place near his Saugerties, New York home earlier that month, he snapped up the offer to play the Isle Of Wight Festival to get as far away from the Woodstock crowds that would be looking for him at home.

Recently released is the archival Bob Dylan release, The Bootleg Series, Vol. 10 – Another Self Portrait (1969-1971). The four-disc collection features a remastered version of 1970's double-disc Self Portrait, along with outtakes from his 1969 Nashville Skyline album, Self Portrait, 1970's New Morning — and finally, the full Isle of Wight performance.

The tracklisting to Isle Of Wight Live 1969 is: “She Belongs To Me,” “I Threw It All Away,” “Maggie's Farm,” “Wild Mountain Thyme,” “It Ain't Me, Babe,” “To Ramona”/”Mr. Tambourine Man,” “I Dreamed I Saw St. Augustine,” “Lay Lady Lay,” “Highway 61 Revisited,” “One Too Many Mornings,” “I Pity The Poor Immigrant,” “Like A Rolling Stone,” “I'll Be Your Baby Tonight,” “Quinn The Eskimo (The Mighty Quinn),” “Minstrel Boy,” and “Rainy Day Women #12 & 35.”