The Tom and Rickie show: Why the relationship of rock's superstar couple was doomed

In 1979, Rickie Lee Jones became the rock superstar that her lover Tom Waits had never been. In an extract from his new biography, Barney Hoskyns recalls the drugs and envy that blighted Waits's wildest romance

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Chuck E Weiss, the subject of Rickie Lee Jones's most famous song, was the one who first alerted Tom Waits to the aspiring 23-year-old singer-songwriter.

Jones was a wild child, a free spirit with boho baggage and a way with language that made people think of, well, Tom Waits. Born in 1954 in Chicago, Rickie was a renegade from a rootless vaudeville family that moved round the country. At 14, Jones ran off to a rock festival in California, freaking out on acid as she beheld Jethro Tull's flute-toting frontman, Ian Anderson. By 1975, she was living in the old beatnik neighbourhood of Venice, waitressing and playing the local coffee-house, Suzanne's. Though Jones was so broke she sometimes slept under the Hollywood sign, her songs made people's ears prick up. One night in the summer of 1977, Chuck E Weiss was washing dishes in the kitchen of the Troubadour club when through the doors he heard the sound of a girl singer. He watched Jones sing two numbers and was knocked out.

Waits first spoke to Jones outside the club on a late summer evening. "The first time I saw Rickie Lee, she reminded me of Jayne Mansfield," Waits said in 1979. "I thought she was extremely attractive, which is to say that my first reactions were rather primitive – primeval even." When he finally saw her perform, he was even more turned on: "Her style on stage was appealing and arousing. Sort of like that of a sexy white spade."

By the end of 1977, Waits and Jones were an item. Lubricated by booze and a shared love of jazz, the Beat poets and West Side Story, the relationship quickly became passionate. "She was drinking a lot then and I was too, so we drank together," Waits said. "You can learn a lot about a woman by getting smashed with her." Waits and Jones not only drank together, they drank (and drugged) with Chuck E Weiss. The three friends ran amok in west Hollywood, gate-crashing parties, to create a parallel world that was equal parts Bukowski and hipster-comic Lord Buckley. "It seems sometimes like we're real romantic dreamers who got stuck in the wrong time zone," Jones told Rolling Stone. "So we cling, we love each other very much."

Jones's songs combined the influences of Laura Nyro and Van Morrison with that of Waits himself. When he heard her "Easy Money", he must have known it was part-mimicry of his own street portraiture. "I always tend to become whomever I am involved with," Jones admitted in 2004, "and so I think I took on his swaggering masculinity. It was a good coat to wear, a good thing to hide behind."

Jones, Weiss and Waits spent the Christmas of 1977 in LA. A new song Waits was working on, "Red Shoes by the Drugstore", hinted at their yuletide capers. Jones was surely the "little bluejay/in a red dress", wearing the shoes Waits was so taken with. The "ski room" that Santa Claus is drunk in was a bar at 5851 Sunset Boulevard that Waits, Weiss and Jones regularly frequented.

During this time, Waits, Weiss and Jones also turned up to attend a party thrown by the brother of Herb Cohen, Waits's manager. Making a beeline for the refreshments, Jones grabbed an avocado pear, sat down in a chair, and inserted it between her legs. Cohen's industry friends were appalled. "Tom was embarrassed but got a great kick out of it," Weiss claimed. "Nobody would talk to us after that, so we spent the evening going up to people with cocktail dip hidden in our palms and shaking hands with them." To Weiss, "as absurd as it may sound", the trio's mindset was "kind of like us against the suits".

When Jones showed up at the cover-shoot for Waits's album Blue Valentine in early September of 1978 (pictured in box, far right), she was flying high on the news that she'd been signed to Warner Brothers Records by the label's head of A&R, Lenny Waronker. Using the photographer Elliot Gilbert, Waits staged the shoot in a 24-hour gas station. For the picture on the reverse of the album, Jones vamped it up in a red jacket, Waits pinning her against the bonnet of his customised 1964 Thunderbird, with Chuck E Weiss hovering in the background. Yet, for all that he liked to portray the relationship as an outlaw romance, Waits was himself slightly intimidated by Jones. "I love her madly in my own way... but she scares me to death," he said. "She is much older than I am in terms of street wisdom. Sometimes she seems as ancient as dirt, and yet other times she's so like a little girl."

But Jones's recklessness masked an insecurity; she said of herself in 1984: "I think [I] was a lot more special than I ever knew, because I didn't think [I] was very pretty or smart... [I] was real scared of everybody and everything." Waits, Rickie felt, had a confidence she would always lack. "He was always, I thought – and maybe this is because I was in love with him – much more charming than me... And he seemed to really be able to make friends with big wheels and do it gracefully on their level."

For Waronker, the obvious choice as Jones's first single was "Chuck E's in Love", a song inspired by a phone-call Waits had received as he and Jones slobbed around one night in his bungalow at the Tropicana motel. It was Weiss calling from Denver to say he'd been smitten by a distant cousin. When Waits uttered the immortal line, Jones seized on it.

By May, after an appearance by Jones on Saturday Night Live, "Chuck E's In Love" was in the charts. By early July it was at number four, well on the way to becoming a sassy boho classic [and taking star billing on her debut, eponymous album, pictured inset, far right], and the beret-sporting, cigarillo-toting Jones – who'd only dared to dream of the cult acclaim accorded her boyfriend – was almost a household name. But success changed everything.

The truth was that Jones was being subtly undermined by Waits. "I started feeling more insecure as my career began," she said. "Maybe it's the influence of other people who were more dominant, without naming names..." Eclipsed by the attention she was getting, Waits was unsure how to deal with it. And as he withdrew emotionally from her, she fell into the consoling arms of heroin. "Tom didn't have as much recognition as Rickie Lee had, and he'd been around much longer," Weiss said. "It was the same with me. I had a bit of envy for what she achieved, too. But she couldn't handle it, man."

"For all the craziness he projects, Tom's a fairly normal guy," says his friend Paul Body, another stalwart of the Troubadour club. "That whole sort of jazz-junkie life was never his thing and I think it might have freaked him out." There were certainly moments of danger that freaked out the middle-class boy from Whittier and Chula Vista, California. "I found myself in some places I can't believe I made it out of alive," he confessed years later. "People with heavy drug problems. People who carried guns; everywhere they went, always had a gun."

The fact Jones was now a star made little difference to her drug intake. She has said she was a heroin addict for two years, though it was a subsequent six months of cocaine abuse that ultimately brought her to her knees. Being with Waits, a man all too familiar with the effects of drugs on jazz musicians, would only have made her shame greater.

Flying with Jones to London in late August, Waits was at her side as she played dates in Edinburgh, Amsterdam, Manchester, Birmingham and London. Before a show at the capital's Dominion Theatre, Jones was photographed clinging to Waits like a little girl on her dad's lap. But Waits knew the relationship wasn't healthy: within weeks of returning home, he had broken up with her.

It wasn't only drugs that made Waits pull back. Jones's underlying dependency was not what Waits needed in a woman, and years later, Jones came to understand that. "I think Tom had his feet on the ground much more than me," she said. "He was making himself up, but he didn't have so much trouble in his background as I did."

The loss of Waits devastated Jones, who holed up with her habit in a suite at LA's swanky Chateau Marmont on Sunset Boulevard and began a six-month slide into cocaine psychosis. Gradually she pulled herself together, pouring her pain into one of pop's great break-up albums: Pirates (1981) was a testament to overpowering grief, perfectly described by Rolling Stone's Stephen Holden as "explosively passionate and exhilaratingly eccentric". In "A Lucky Guy", she foolishly told Waits she loved him, her girlish soprano only underscoring the sense of unrequited adoration. "Living it Up" told the tale of the Waits/Weiss/Jones triad, casting them as Louie, Eddie, and Zero.

Ultimately, Waits's break-up with Jones was symptomatic of a more general desire for change. He was tired of playing "Tom Waits" for people who couldn't see the true depths of his music, who wanted jokes from a performing seal. By the end of October 1979, he was "poised on the threshold on some sort of a new direction". Within a year, he was married to Kathleen Brennan and plotting a wholesale reinvention of his musical persona.

© Barney Hoskyns, 2009.

An edited excerpt from 'Lowside of the Road: A Life of Tom Waits', by Barney Hoskyns, published by Faber & Faber at £20

What happened next

Tom Waits After splitting with Rickie Lee Jones in 1979, Waits married Kathleen Brennan and distanced himself from his trademark jazzy, bluesy sound.

Chuck E Weiss The Colorado-born singer-songwriter met Waits in 1972, becoming the subject of Waits's songs such as "Jitterbug Boy". Weiss recorded his first album, Extremely Cool, in 1999.

Rickie Lee Jones Her 1979 single "Chuck E's in Love" turned her into a star overnight, but Jones's success was blighted by drugs problems in the early-1980s. She had a daughter in 1987, and continues to record and tour.