You could call it Woodstock on Woodside Bay. On August 29th and 29th of 1969, the Isle of Wight – four miles off the mainland coast – hosted its second annual music gala, an event that brought over 100,000 listeners to the fields of Woodside Bay in the village of Wootton. The three day festival featured a swath of British acts and a handful of American artists, but in truth, the presence of one man dominated  the festival.

1. Isle of Wight Festival 1969

Bob Dylan hadn't performed live in three years. Agreeing to appear at the festival, Dylan was to be joined by onstage by The Band. "My job is to play music," he told the press, days before the performance. "I'm just going to take it easy. You've got to take it easy if you're going to do your job well."
Dylan may have been trying to underplay the whole situation but audience expectations couldn't be higher.  

Festival footageMore »

2. Bob Dylan

 In retrospect, the expectations were far too high. Although exuberant, the hour-and-change performance was a bit ragged with an uneasy Dylan obviously reacting to the crowd's anxious mood. Dylan had been off the stage for too long; a live performance in front of 100, 000 listeners may not have been the best way to break the ice.

Although a few selections from the concert were first released on the 1970 Dylan album, Self Portrait, the entire set can be heard on The Bootleg Series Vol. 10: Another Self Portrait (1969–1971) .

 

Set list:

• 1. She Belongs to Me 
     
  2. I Threw It All Away 
     
  3. Maggie's Farm 
     
  4. Wild Mountain Thyme 
     
  5. It Ain't Me, Babe 
     
  6. To Ramona 
     
  7. Mr. Tambourine Man 
     
  8. I Dreamed I Saw St. Augustine 
     
  9. Lay Lady Lay 
     
  10. Highway 61 Revisited 
      
  11. One Too Many Mornings 
      
  12. I Pity the Poor Immigrant 
      
  13. Like a Rolling Stone 
      
  14. I'll Be Your Baby Tonight 
      
  15. Quinn the Eskimo (The Mighty Quinn) 
      
  16. Minstrel Boy 
      
  17. Rainy Day Women #12 & 35 
      

 

"I Threw It All Away" (Isle of Wight 1969)

3. The Band

One of four acts – including The Who, Richie Havens and Joe Cocker – that also appeared at Woodstock little over a week before, The Band put in double duty at the festival, both supporting Dylan and performing a full set before he joined them. The group's first appearance in Britain was well received, but the crowd was obviously eager for Dylan to hit the stage.Drawing from the influential 1968 release, Music From Big Pink, The Band performed such signature songs "We Can Talk," "Chest Fever" and "I Shall Be Released," saving "The Weight" for the final number. The encore found the group diving into a spirited rendition of the Four Top's hit "Loving You Is Sweeter Than Ever."

"The Weight (Isle of Wight 1969)

4. The Who

With the May release of the ambitious double album, Tommy, The Who were right on the cusp of superstardom when they appeared at The Isle Of Wight festival. The group's rousing appearance featured Who favorites and a nearly complete turn through the new album. The band's dazzling set the next year was captured on the film, Live at the Isle of Wight Festival 1970.

 Amazing Journey/Sparks (Isle of Wight 1969)

5. The Beatles

 Well, not really, but John Lennon, George Harrison and Ringo Starr were among the masses eagerly awaiting Dylan's return to the stage. Eric Clapton and Keith Richards and Charlie Watts of The Rolling Stones also attended the festival as spectators along with such celebrities as  Elizabeth Taylor and Richard Burton and Jane Fonda.

Beatles in audience (Isle of Wight 1969)