Like so many female musicians from the ’60s, Dana Gillespie got more attention for the famous men she was associated with than her actual musical talent. Considering the fact that her romantic involvements included David Bowie, Bob Dylan, Jimmy Page, Keith Moon, Mick Jagger and others, this isn’t particularly surprising…but that doesn’t mean her music didn’t (and doesn’t) deserve more credit.
The future singer-songwriter was born Richenda Antoinette de Winterstein Gillespie in 1949 to a London-based radiologist father of Austrian nobility and a mother descended from a long line of Norfolk-landowners, according to the Guardian. Her parents were remarkably liberal for the time, which probably explains why she was allowed to go to Soho’s Marquee Club as a young teenager.
“It was just so bloody exciting,” Gillespie recalled. “Everyone was attempting to play the blues back then.”
It was at the Marquee that her life changed forever when she saw Bowie (still Davie Jones at that point) play a set. Afterwards, Bowie, then 17 years old, asked Gillespie, 15, to take him home for the night.
“Of course, I said yes,” Gillespie recalled, adding that she introduced him to her parents the next morning while wearing her school uniform. Gillespie and Bowie’s relationship, both personal and professional, would last for another decade.
Their romance was not an exclusive one, however. In 1965, Gillespie caught Dylan’s eye during a press conference at London’s Savoy hotel. Dylan invited her back to his room, and then, to accompany him on tour. Gillespie can even be seen in the documentary Don’t Look Back, the documentary about Dylan’s British tour.
“I was very young then — a couple of weeks past 16, so I was just about legal, but, in those days, nobody cared about what anybody did,” Gillespie told hi-fi+ in 2025.
“There was no social media, you just went and had fun,” she continued. “Dylan was always a gentleman and extremely nice.”
Silver Screen Collection / Getty Images
Gillespie’s own career was picking up around that time, too. She was signed by Pye Records and released several singles, including “Thank You Boy,” produced by Page (also a love interest and a “gentleman at all times”).
While none of those singles were commercially successful, that didn’t stop Gillespie from making albums and performing; in fact, she’s released a staggering 74 albums over the course of her career.) She sang sessions with Reg Dwight (before he was Elton John) and played in clubs, bars and West End musicals. Bowie wrote the song “Andy Warhol” for her and her backing vocals can be heard on his Ziggy Stardust album. Eventually, Bowie and guitarist Mick Ronson produced Gillespie’s 1973 album, Weren’t Born a Man, which included her singing a cover of “Andy Warhol.”
Unfortunately, that album wasn’t a success either. Gillespie was forced to support herself as an actress, instead, appearing in movies such as The People That Time Forgot and Bad Timing, though she “was never serious about acting.”
Gillespie’s path took a turn when she started following the late Indian spiritual leader Sai Baba, which inspired her to start recording albums of Indian devotional music.
“I grew as a singer and a person,” she recalled.
In 2024, at the age of 75, Gillespie released her 74th album, First Love, a diverse collection of mostly covers including songs by Green Day (‘Boulevard Of Broken Dreams”), Leonard Cohen (“Dance Me To The End of Love”), Dylan (“Not Dark Yet”), Bowie (“Can You Hear Me?”) and others.
“If I’m lucky enough to make another album by the end of this year, it will be 75 — I can say one for every year,” she said at the time.
Related: Iconic Singer-Songwriter, Who Paved the Way for Bob Dylan and Joni Mitchell, Vanished Without a Trace 52 Years Ago
Leave a Reply