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This is the fifth in our series of five seminal album covers by female artists

I’m pretty sure my Dad had a really big crush on Rickie Lee Jones. Her name resonates for me because he was a huge music fan and started buying CDs when the format was released. He bought all of hers as soon as they were reissued and I vividly remember looking at this cover when I was a kid and listening to her biggest hit Chuck E.’s in Love.

It turns out that my Dad was not alone in his affections. In researching this cover, I’ve come across plenty of love letters to the Jones that appeared on the scene in 1979, with her alluring air of hipster cool. Blogger Al Barger puts it this way: “Obviously, Rickie was THE ultimate romantic fantasy object of any cool guy my age…The time less spiritual of my classmates were spending concentrating on the Farrah Fawcett poster or some such, I spent enthralled with that album cover with the beret and chewing on the cigar.”

At the time she was in a relationship with one of the only guys on the planet who could match her in the cool stakes (and shot for shot). Jones and Tom Waits were known as rock music’s “bohemian couple”. The first sleeve she ever featured on was Wait’s 1978 Blue Valentine and the photos on the back cover make for an image that is even parts trashy and alluring.

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A quote on the Tom Waits Library provides more detail about their romance: “The first time I saw Rickie Lee she reminded me of Jayne Mansfield. I thought she was extremely attractive, which is to say that my first reactions were rather primitive – primeval even. Her style onstage was appealing and arousing, sorta like that of a sexy white spade. She was drinking a lot then [1977] and I was too, so we drank together. You can learn a lot about a woman by getting smashed with her.”

Getting smashed was something that the young and beautiful Jones was extremely keen on and it would be naïve to suggest that her aura of cool wasn’t sustained by rampant self-destruction. In 1979 she staged a remarkable breakout, with a single and an album in the Billboard Top Five and five Grammy nominations. She even made the cover of Rolling Stone Magazine (the issue that sold like hotcakes).

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Time Magazine dubbed her ‘The Duchess of Coolsville’. She was greeted with the kind of critical and commercial adulation enjoyed by Amy Winehouse – and I make that comparison in more ways than one. In recent interviews, she has talked about “using drugs to the extent that you know this time you might die. Whereas some people seem able to take dope a little bit for their whole lives, they are not going to take it to their demise. And those of us who are addicts are in great danger because nothing is ever enough.”

The photo and cover design are by Norman Seeff, who was responsible for Playing Possum sleeve and for the portrait of Mitchell used on the Hejira cover. I realise that this series of covers by women artists has also become something of a Seeff retrospective as well, which is testament to how incredibly in demand we was in the seventies. It’s well worth visiting his site to gawk at all the famous faces that he has helped to immortalize.

In this portrait of Jones, he creates a bohemian and jazzy atmosphere that evokes the music on the album. An article in The Guardian perfectly describes the appeal of this album cover, which “became iconic – the hollowed cheeks, beatnik beret, dangling cheroot; she looked so cool.” But for a beautiful woman in her mid-twenties her face is far too care-worn and gaunt. Her focus is exclusively on her smoke and the intensity with which she regards it tells you much of her compulsive nature. It’s not clear whether the beautiful light behind her denotes sunrise or sunset – but if it’s morning you assume she hasn’t been to bed and if it’s evening that she’s just woken up.

She could be Winehouse or Cat Power, or even Courtney Love, but perhaps she was one of the first women to realise (even subconsciously) that her weaknesses could become her brand; her addiction her hallmark.

Another famous cover from the 1979 was Marianne Faithfull’s Broken English, who had a substantial head start grappling with addiction.

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Faithful seems to be holding the cigarette more out of habit than anything else and the blown out lighting and gesture instantly brings to mind the squinting pain we all feel doing the “walk of shame” after a big night. It’s just that her big night had been going for over a decade.

Today, both Jones and Faithfull are clean. They are still writing, recording and performing music. Former ‘it’ girls, they are now something far more admirable – battle-scarred survivors who have seemingly wrestled their demons and come out on top.