In 2002, she signed a management deal with American Idol creator Simon Fuller's 19 Entertainment, a publishing deal with EMI and a label deal with Island UK. Later that year, she went to Miami to record her first album with Salaam Remi, who had produced music for Nas and the Fugees. "She came over and sat down and I was like, 'So what do you do?'" recalls Remi, who continued working with Winehouse until her death. "She picked up an acoustic guitar, started singing 'Girl From Ipanema,' and pretty much just lit up the whole room." Her jazzy 2003 debut, Frank, earned critical raves and awards at home, including a nomination for the Mercury Music Prize and the Ivor Novello Award for songwriting.
But as strong as her debut album was, it barely hinted at the greatness of the record that would follow. On Back to Black, Winehouse underwent a remarkable transformation – from a conventionally pretty, promising performer to a tattooed, beehived diva belting songs about desperate love. She started dating Fielder-Civil in 2005, and the pair would hang around her local Camden bar spinning classic girl-group and Motown tunes on the jukebox, playing pool and, especially, drinking. She attributed the shift from her early jazz sound to the Sixties R&B of Back to Black to her transition from being a stoner to a drinker. "I used to smoke a lot of weed," she told Rolling Stone. "I suppose if you have an addictive personality, then you go from one poison to the other. The whole weed mentality is very hip-hop, and when I made my first record, all I was listening to was hip-hop and jazz. The weed mentality is very defensive, very much like, 'Fuck you, you don't know me.' Whereas the drinking mentality is very 'Woe is me, oh, I love you, I'm gonna lie in the road for you, I don't even care if you never even look my way, I'm always gonna love you.'"
She re-teamed with Remi for some of Back to Black, but the stroke of genius was pairing her with producer Mark Ronson, who had built his reputation as a DJ but had begun producing songs for Lily Allen, Sean Paul and Christina Aguilera. Ronson recruited the eight-man Brooklyn funk-and-soul crew the Dap-Kings to back Winehouse on tracks including "You Know I'm No Good" and "Rehab," imparting an authentic retro-cool vibe perfectly suited to Winehouse's aesthetic. "It was obvious that she knew the difference between what sounded good and what sounded bad," says Dap-Kings guitarist Binky Griptite, who toured with the singer in 2007 and remained her friend. "She had good taste. That's increasingly rare. There are so many artists whose record collections only go back five years. You gotta know some history, and she knew some history. That's why we're sitting here talking about her."
Ronson recognized the huge-voiced singer with a bad-girl look as part of a tradition stretching back to the Sixties. "The Shangri-Las had that kind of attitude: young girls from Queens in motorcycle jackets," he told ROLLING STONE at the time. "Amy looks fucking cool, and she's brutally honest in her songs. It's been so long since anybody in the pop world has come out and admitted their flaws, because everyone's trying so hard to project perfection. But Amy will say, like, Yeah, I got drunk and fell down. So what?' She's not into self-infatuation and she doesn't chase fame. She's lucky that she's that good, because she doesn't have to."
(Upon learning of Winehouse's death, Ronson expressed heartbroken shock, tweeting, "She was my musical soulmate and like a sister to me. This is one of the saddest days of my life.")
The exposure brought on by Winehouse's ballooning fame – and the demand to tour behind the album – accelerated her decline. "She was always questioning her own ability," says Dougie Charles-Ridler, a longtime friend and the owner of the Hawley Arms, a favorite hometown pub. "She'd have a shot of tequila or a glass of wine just to settle her nerves. She needed more of that to settle her nerves as time went on, and it got kind of out of control." And her vulnerability was obvious to the people close to her. "There was one time on the Back to Black tour when the tour manager was looking for Amy, and she was two hours late," adds Charles-Ridler. "Suddenly there's someone banging on my door, and I open it, and it's Amy. She ran and jumped in my bed and hid under the duvet. And it just showed. She was just so scared."
Winehouse briefly went to rehab in early 2008 after U.K. tabloid The Sun published a video of her smoking crack, but subsequently told Rolling Stone'S Claire Hoffman that she was on drugs the whole time she was there. Almost as soon as Winehouse won her five Grammys in February, accepting them via satellite due to a visa issue, the focus began to shift from anticipating her next album to anticipating her next public meltdown.
During her separation from Fielder-Civil after his incarceration, things got worse. In one bizarre incident, a video surfaced on YouTube of a wasted Winehouse and notorious ex-Libertines singer Pete Doherty playing with newborn white mice, their fingernails caked with what appeared to be black resin. But Winehouse remained remarkably unguarded, despite the army of paparazzi camped out in front of her house (and whom she occasionally would send on errands). "To be honest, my husband's away, I'm bored, I'm young," Winehouse told Rolling Stone. "I felt like there was nothing to live for. It's just been a low ebb."
But by early 2009, Winehouse seemed to be doing better. She traveled to the Caribbean island of St. Lucia for several months, where she reportedly kicked hard drugs. The singer's gaunt frame started filling out, and island life seemed to revivify her spirit. She formed deep bonds with locals, in particular Marjorie Lambert, the 57-year-old owner of Marjorie's Beach Bar & Restaurant, a sweet little bam-boo-and-wood cabin whose specialties are creole-style seafood and spiced rum punch. Occupying a pair of villas on the grounds of the nearby Cotton Bay Village resort, Winehouse found a kind of privacy she never got in London. Sometimes she would play a song on the white baby grand in the lobby of the resort or surprise tourists by performing Back to Black songs on Marjorie's karaoke machine. She became so close with one of Lambert's six grandchildren, an eight-year-old named Dannika, that she began inquiring about adopting the girl. And when a friend of Lambert's was suffering from a hernia and couldn't afford the operation, Winehouse offered to handle the $6,000 cost. "She helped so many people here," Lambert says. "She would be everybody's friend, and she loved children. She'll be there just like us, sitting, eating together, laughing together, giving jokes, you know?"
Winehouse and Fielder-Civil finally split in early 2009, when he filed for divorce after photos surfaced of Winehouse snuggling with a new beau in St. Lucia. They legally divorced in August that year. (Fielder-Civil recently returned to prison to serve a 32-month sentence on burglary and firearms charges.) And early last year, Winehouse showed further signs of improvement, successfully re-teaming with Ronson to record a cover of Lesley Gore's 1963 hit "It's My Party" for a Quincy Jones tribute album and seeming healthy and happy during the session. She kept busy in other ways, too – she started a label, Lioness, to release music by her goddaughter Dionne Bromfield, a teen soul singer after her godmother's own heart. This past March, she joined Tony Bennett at Abbey Road Studios to record the Thirties jazz standard "Body and Soul" for Bennett's upcoming Duets II album. "She was an extraordinary musician with a rare intuition as a vocalist," Bennett said. "She was a lovely and intelligent person, and when we recorded together she gave a soulful and extraordinary performance."
As much as she prized her Camden hometown, the notoriously gritty Northern London burg where Winehouse had lived ever since moving out of her mother's house, it was not a good place to escape bad habits. In the days after her death, some Camdenites even said they didn't think her benders were that bad, compared to their own. "People often dismiss Camden Town as a place where drug addicts gather, lost souls," says Richard Osley, deputy editor of the Camden New Journal. "There was an affection among Camden regulars for her. If she was a mess-up, she was their mess-up. Everybody felt the same: neighbors, the local news agent, the local cafe, the Marathon kebab house where she would turn up late at nights, and so on. That's why people were hoping she would pull through."
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