In '65, she swapped her skies for a micro- phone after being discovered singing at the Marquee club in London by arch-folkie Donovan and started dating her. Dana first met Dylan on his 1965 English tour when she was 16. They saw each other whenever he came to England and built an enduring friendship.
with Bob Dylan 1965
with David Bowie 1970
Three 45's cut for Pye between '65 and '67 included songs written by Carter & Lewis and The Hollies, whilst Donovan himself had written "You Just Gotta Know My Mind" in '65. Recorded in the U.S. by Karen Verros that same year, Dana's storming version didn't appear until late '68, by which time she had switched to Decca. Some of her recordings as a teenager fell into the teen pop category, such as the 1966 single "Thank You Boy", produced by Jimmy Page who she also had a relationship with.
After a high-profile, Bowie-associated period during the early 70's, Dana switched to serious blues. She had a relationship with Mick Jagger in 1976. In 1997, her revamped band opened for Bob Dylan's UK tour". In 1998, Dylan rang asking her to support him on tour. When asked why, he replied “Because you’re a great songwriter and you’ve always been nice.” To Gillespie, Dylan will always be the perfect gentleman. “He’s amusing, he’s spiritual.