The 1969 Isle of Wight Festival was held on August 30–31, 1969, at Wootton, and attracted an audience of approximately 150,000 to see the acts of Bob Dylan, The Who and Free. It was the second of three music festivals held on the Isle of Wight between 1968 and 1970. Organised by Fiery Creations, aka brothers Ronnie and Ray Foulk, it became a legendary event largely owing to the reappearance of Bob Dylan. The event was well managed and trouble free.
The festival was so much larger and more popular than the year before due to Dylan's performance. He hadn't played publicly for 3 years following a near fatal motorcycle accident, July 1966. Shunning the Woodstock festival held practically on his doorstep, Bob Dylan was initially reluctant to perform his comeback show on this little known island. After weeks of negotiations the promoters showed him a short video of the Island's cultural and literary heritage. This appealed to Dylan's artistic sensibilities as he was enthusiastic about performing in Tennyson country. Prior to the festival Bob Dylan and The Band rehearsed at Forelands Farm in Bembridge, and were joined by The Beatles minus Paul McCartney. Among the 150,000 audience members were John Lennon, Yoko Ono, Ringo Starr, George Harrison, Rolling Stones Keith Richards and Bill Wyman, Syd Barrett, Eric Clapton, Elton John and Jane Fonda.
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On 31 August a nervous Bob Dylan arrived on stage in a cream suit recalling Hank Williams, with a haircut and a short beard, performing his recent pieces from Nashville Skyline and John Wesley Harding: much to the surprise and confusion/consternation of the audience. During the press conference prior to his performance, Dylan remarked that he came to the Isle of Wight to see the birthplace of Alfred, Lord Tennyson, because he was "just curious." John Lennon opined that his performance was reasonable, though slightly flat; and still the audience was waiting for Godot or Jesus. Eric Clapton, however, was mesmerized, clearly - as he has stated, being inspired back to the blues and country by Bob Dylan and The Band's album Music From Big Pink - saying "Dylan was fantastic. He changed everything. ... [The audience] couldn't understand it. You had to be a musician to understand it." Levon Helm commented on their latency on the bill: "Bob had an extra list of songs with about eight or ten different titles ... that we would've gone ahead and done had it seemed like the right thing to do. But it seemed like everyone was a bit tired ... the festival was three days old by then." Tom Paxton mentions the "negative reaction in the British press, including downright fabrications: like saying he had run off stage half-way through. ... I went with him and The Beatles to the farmhouse where he was clearly in a merry mood because he had felt it had gone so well. ... The Beatles had brought a test pressing of Abbey Road and we listened to it and had quite a party."
Dylan' setlist was as follows:
The Who presented their standard set at that time, which included the rock opera Tommy as they had recently released that album and were touring in support of it. They had just returned from a tour of United States where they had performed at Woodstock about two weeks earlier. Keith Moon looked depressed. They opened with "Heaven And Hell," "I Can't Explain," "Fortune Teller," "Young Man Blues," and then performed the opera nearly in full, finishing up with "Summertime Blues," "My Generation" and "Shakin' All Over."
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