Dana Gillespie: Bowie, Dylan, Sean Connery, avalanches

In Weren't Born a Man, Gillespie herself opts to begin her story with two pages of bullet points to remind us that, among other things, she was British junior water ski champion for four years, spent time with Dylan and hung out in his hotel suite with the Beatles, enjoyed "wild times" with Keith Moon, Michael Caine, the aforementioned Connery, and the cream of 1960s' rock royalty and recorded with Jimmy Page and Elton John.

And that's just the first four of said bullet points. Andy Warhol, Peter Cook, Ken Russell, Princess Margaret and Spike Milligan and Sir John Gielgud all get a mention before the end of the first page.

In short, it is possible – or, let's be honest, probable – that Gillespie has lived several more lifetimes than the rest of us.

Gillespie's book is a catalogue of friendships and encounters that take in a privileged if eccentric childhood, her wild teenage years, her lovers (never has the word "horizontal" carried quite the weight of innuendo as it does here), her professional life as a musician (from performing in Jesus Christ Superstar to supporting Dylan on tour) and her awakening spirituality and visits to India to see her guru Sathya Sai Baba.

"It's not boring, I think," she says of the result. I'd say that was fair comment.

Dana Gillespie, 15, in her early days as a folk singer

It is December when we speak. She is at home in London where she lives alone. Gillespie is now approaching her 72nd birthday. She has had a rather productive pandemic. She not only finished her book, but two albums as well.

"I'm not Tik-Tokking and Instagramming or Snapchatting," she points out. "I'm pleased if everyone else wants to do that, but I can't be arsed.

In conversation she remains sparky, opinionated (not all of them, it should be said, PC), amusing and self-possessed, a raconteur with no shortage of good stories to tell. She is happy to embrace her age, but not ready to lie down to it.

"I put henna on my hair, but I definitely wouldn't go under the scalpel. I have earned my wrinkles."

Well, indeed. Gillespie's life story is one of a Stakhanovite appetite for work (she has recorded more than 70 albums) and perhaps a sybaritic taste for pleasure.

She started writing the book a decade ago, but it's taken time. Possibly because she had to work out what to include and what not. "I didn't want the book to be a bonkbuster, although plenty of people might have wanted that. Lord knows, I could have made it far more horizontal in a way. But I have taste and hopefully I have class."

Dana Gillespie Recording “Ain’t Gonna Play No Second Fiddle” with Phill Brown at Island Studios.

The class is a given, you would think. She was christened Richenda Antoinette de Winterstein Gillespie. Her mother was a descendant of the Gurney family, English quakers who set up a bank that eventually merged with Barclays.

Her father, Hans Heinrich Winterstein (or "Dadster" as she called him) was a medical man who trained in Edinburgh and adopted the surname of the Scottish doctor who sponsored him.

He knew the Mitford girls and before moving to South Kensington, Gillespie spent her first 10 years living in a house in Woking designed by Edwin Lutyens, with a garden laid out by Gertrude Jekyll.

Gillespie speaks of her parents with some fondness.

"I couldn't have found a better set of parents who were liberal enough to let me be adventurous and do what might have seemed crazy, weird stuff from a very early age. Some parents might have complained. My parents didn't because they were bright. My father was a great intellectual and very witty, very good-looking. Women fell horizontal when they met him. Not so easy for mother. She found happiness with her next husband.

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"I was very close to both of them. I feel sorry for people if they don't get to learn from the experience you get from your parents."

This is true, although most fathers, I point out, don't move their mistresses into the house they share with their wife, as her's did.

"But you know, it worked. The house was big. There were five floors and a basement.

"The top two floors were my mother, my father had the next three floors, and I had the basement. I was as happy as a pig in shit at 15. To have your own flat with your own entrance and a little garden at the back where my dogs would go. It was brilliant."

As a young teenager, Gillespie was a water skier and then a skier and had sporting success in both. Not even being caught in an avalanche at the age of 15 stopped her.

"My knee got better," she points out. "But as I went on it got more painful. It was really bad when I was in Jesus Christ Superstar because the rake of the stage was quite steep. So, every night I'd be singing 'I don't know how to love him,' and my knees would just crunch up."

She's since had both her knees replaced. "So I am bionic."

In her early teens Gillespie started going to clubs in London and her life began to shift from sport to music.

"When I went to the Marquee Club when I was 13 my whole life changed. I walked in and there was a blues band playing – I think it was the Yardbirds – and I was completely hooked."

Photoshoot for her 1968 album Foolish Seasons. Photograph Gered Mankowitz. GERED MANKOWITZ © BOWSTIR Ltd. 2021/mankowitz.com

Who was that teenage girl, Dana?

"Hungry for music. I always wanted to be a songwriter. When I was 14, 15, I used to sit, sometimes with Bowie, in this cafe in Tin Pan Alley called The Giaconda waiting for music publishers. They would run down the road to ask, 'Is there a backing singer or a bass player?' And you would have a session. I just knew I had to follow this extraordinary thing called music."

Bowie. Of all the people she has been associated with, he was perhaps the closest. In 1964 she caught the Manish Boys, fronted by one David Jones (this was before he changed his name), at the Marquee Club. After the gig she was at the bar brushing her waist-length peroxide blonde hair when Jones came up behind her, took the brush from her hand and asked could he come home with her. "Of course, I said yes," she writes.

When he bumped into Gillespie's parents the next morning, Gillespie says, "my father first thought Bowie was a girl. But he wouldn't have minded that either. He was very easy-going."

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You say in the book, I remind her, that when it came to Bowie, you knew it would never be a normal boy/girl relationship. Was that what you wanted?

"With anyone, you mean? Certainly not then, not in the sixties. I was far too young. In the seventies I was having far too good a time, although I did have a five-year relationship with an antique dealer.

"I've never really been one who was very comfortable on the arm of somebody very famous. And I never really met anybody I wanted to marry. I was very independent. I had loads of affairs, but not ones that made me want to change my name. I never wanted children. I'd rather be in the studio . I'd rather be writing songs. I've done that since the age of 11. That's 60 years."

Gillespie remained friends with Bowie in the lean years that followed, even lived with him and his then wife Angie, before watching him go stratospheric with Ziggy Stardust.

In the decade she knew him, she says, he didn't change much. "He was always the same to me. I didn't care whether he was doing the Hollywood Bowl with Diamond Dogs or it was me and his then wife Angie hanging out when he lived in this place called Haddon Hall. He was driven. I recognised his God and his God was communication."

Gillespie "at David Bowie's piano at the Sherry Netherland Hotel in New York

Gillespie is very insistent in the book that she and Angie were themselves never lovers, as the latter claimed in her own memoir, but she did once end up in bed with both Angie and David and her then boyfriend Ken Petty.

"Those were the days," Gillespie says. "People were quite experimental. Remember, we had just come out of the sixties and people swang in a different way. You can't do anything these days. There's not much fun going on for young people these days.

"We had a great time. The pill had been invented. Aids hadn't been invented. We were all young, good-looking, swanning around the world in first class. And the circle of friends that we all hung with – like the Stones – were people who were in that same situation. So, perhaps one was a bit more experimental than normal.

"But when you're young, and suddenly everything is out there, you get on with it and learn sometimes by your mistakes."

She is not shy of naming her lovers in the book, although sometimes, she writes, they were just "mates with benefits". Jimmy Page, Dylan, Sean Connery – "Well, he was between wives," she says when I bring his name up – Michael Caine and Mick Jagger ("Then again," she notes in the book, "who didn't sleep with Mick?")

When you were 17, I remind her, the businessman John Bloom sent her to report back to him on the orgy scene in California.

"How I got to this house in the Hollywood Hills I can hardly remember. I think took a taxi and literally walked in on a kind of orgy."

"Now, I had been working for quite a few months for John Bloom. He had about four clubs in London. The Crazy Horse Saloon was one of them and I was a singer singing with a trio. I had just passed my driving test. I would sing in these four different clubs.

"And he was a bit of a rascal in those days. The place was filled with girls. Topless barmaids. It was a whole other world … "

She returns to the start of the anecdote. "So, I was out there in Hollywood and it seemed to be kind of orgy time. This guy used to hold orgies once a week on a Wednesday which was the day I arrived. That was quite an eye-opener.

"I've always been a bit of an observer," she adds. "I would rather have a cat on my lap and some chocolate."

As a young woman how she looked was very much part of the packaging when it came to selling the music. The cover of Weren't Born a Man features outtakes from the infamous photograph session she did with Gered Mankowitz for the 1973 album of the same name on which she appeared kohl-eyed and dressed in a bustier and stocking and suspenders ("It attracted quite a lot of attention!" she notes in the book).

And she was constantly being objectified by the press.

She is surprisingly sanguine about it all now. "I realised I have to be realistic. I mean, I was never flat-chested. I knew perfectly well that the newspaper would sell better if the top button was undone, so I just kind of got on with it.

"But those days you dealt with tossers and w*****s because that's how people were. You'd never take it seriously. I would never say, 'Somebody groped my tits. My life is ruined.'

" We are now so squeaky clean. I miss the days that you could walk down the streets and a lovely workman would wolf-whistle as you walked past. You'd get arrested if you did that now. There's no sense of humour anymore. Everyone is so goddamned serious."

Hmm. Such sang-froid. The result of someone who was born into privilege and with enormous self-confidence, perhaps.

She is aware of her own advantages. "I was so self-confident because I could sing," she replies. "I knew I looked good. I came from a family where I was not poor. I was never out of work much, except Bowie and I were the only two in London who auditioned for Hair and got turned down."

We should talk about music. After singing in clubs and cutting her first albums, Gillespie sang on the Top of the Pops compilations that were everywhere in the early 1970s; rerecordings of the hits of the day, with a model on the cover. "There was always a dodgy bird bursting out of a bikini," she says laughing.

"Elton, me and the lead singer from Uriah Heep, David Byron, we did most of them. I was given all the Joan Baezy stuff. We got 25 quid a track. It was great money in those days."

Her own first records were folky affairs, but by the 1970s, by which time she was signed to Bowie's management company MainMan, her voice began to garner a huskiness that leant itself to singing Bowie covers (she recorded a fine version of his song Andy Warhol) and increasingly blues tunes.

"In 1980, when MainMan and Bowie and the whole mad circus fell to pieces, I went to see the boss of Ace Records called Ted Carroll.

"I knew I'd have a sell-by date if I stayed in the pop business. I said I wanted to do an album with the rudest blues songs from the twenties and thirties, all the sex songs, and I want to call the LP Blue Job and he laughed and said, 'Sign here' and I've stayed with them ever since."

In the years since she has sang the blues everywhere from the Edinburgh Fringe to Mustique, where she also hung out with Princess Margaret. (It was Gillespie who introduced Ma'am to the actor and minor gangster John Bindon.)

That career in the blues grew alongside her growing interest in spirituality after she discovered the works of Sathya Sai Baba and started visiting him every year. She even recorded albums in Sanskrit. "I sang western music a lot at Sai Baba's," she points out. "But I had to clean up my lyrics. You can't sing 'Big 10 inch' in an ashram."

Oh, she's a joy to talk to. By the end of our time together I'm just throwing names at her and she's telling me stories. What about Dylan, I say.

"I think he's a bit of an enigma. In '65 and '66 he was over in England doing his tours. We were friends, but with a bit of horizontal life attached to it.

"I got to see him again when he asked me to be the opening act for his tour and that's when we really did talk because he came over to my house. I probably would have offered him anything, but in the end all he wanted was fennel tea.

"It was such an honour to be on the road with him, such an honour that he said he liked my songwriting.

"You can't compare him to anyone and he's a brilliant songwriter. And quite funny too."

So is she, of course. More than that, Dana Gillespie is a force of nature. Like avalanches. Or orgies for all I know.

Weren't Born a Man by Dana Gillespie is published by Hawksmoor Publishing, priced £19.99