Bob Dylan & Dana Gillespie
During the same 1965 U.K. tour in which he snubbed Joan Baez, Dylan took up with a busty 16-year-old English pop singer named Dana Gillespie and holed up with her in his hotel room during subsequent visits to England. “I guess he was juggling women, like most musicians,” said Gillespie in Down the Highway: The Life of Bob Dylan. Gillespie relates a story about Dylan borrowing her orange and pink flowered pants and leaving her in his hotel room, saying he’d be back with them in a few hours. “I was stuck in my underwear because he had taken my trousers. He could fit into mine, but I couldn’t fit into his. I had to sit in the hotel waiting for him to come back. He said, ‘I’ll only be a few hours.’ It was about 15 hours before he came back.” Of Dylan, Gillespie reflects, “He’s amusing, he’s spiritual. Women prefer to be seduced by a brain than bullock. Brains go a helluva long way.”Gillespie would go on to also charm Donovan, Mick Jagger, Jimmy Page (who produced her 1966 single “Thank You Boy”), and David Bowie (who taught her to play guitar). In 1997, Gillespie was invited by Dylan to open up his U.K. tour.