This story is from the August 18th, 2011 issue of Rolling Stone.
Sitting in a popular Miami diner with rain pouring down outside, Amy Winehouse and her new husband, Blake Fielder-Civil, had plenty of reasons to celebrate. "Rehab" was racing up the charts, and the pair had snuck off that morning to get married. When the giant frozen-strawberry cocktail she ordered appeared, Winehouse delighted in the drink's over-the-top tackiness: "It's called the Big Pink-arita!"
I was interviewing Winehouse for her 2007 Rolling Stone cover story, and had met her five days earlier, in Toronto. The marriage was a surprise; during our first meeting Winehouse had been inconsolable after a vicious fight with Fielder-Civil. At the diner, she glanced over and pointed at my cheek. "You've got an eyelash right there," she said sweetly. "You've got to make a wish. I would have got it for you, but it might be weird if I reached over and touched your face." Her tender gesture was as disarming as her obvious intoxication – and the white powder visible in her nostrils from her frequent trips to the bathroom – was disturbing. "I look after people," she later said. "I'm very loyal. Very defensive. I'll always stick up for someone."
This is the Winehouse her friends and family knew: a sweet, maternal nature paired with a bottomless appetite for self-destruction. It all ended tragically at her London apartment on July 23rd, when Winehouse was found dead at the age of 27. Police called the singer's death "unexplained" while they await results of a toxicology report, but her family believes that her death was caused by withdrawal brought on by an attempt to quit alcohol cold-turkey – following a disastrous attempt at a comeback tour in June. "Three years ago, Amy conquered her drug dependency," her father said at her July 26th funeral in London, which was attended by friends including Kelly Osbourne and producer Mark Ronson. "The doctors said it was impossible, but she really did it. She was trying hard to deal with her drinking and had just completed three weeks of abstinence." Winehouse's father told congregants that his daughter had not been depressed, and had been happily playing drums and singing in her apartment the night before.
As Back to Black, her great, defining second album, shot back into the Top 10, crowds gathered outside her Camden home, creating a makeshift memorial with flowers, paintings, cigarettes and bottles of vodka. "She knew what she was capable of and didn't even need to try," wrote Adele, whose current chart-topping success is hard to imagine without Winehouse opening the door. "If she wanted to do something, she would, and if she didn't, she'd say fuck off. Amy paved the way for artists like me."
Winehouse's voice was husky and sultry and sad, like a broken heart marinating in whiskey and cigarette smoke. It sounded like it came from another time, echoing Sarah Vaughan and Billie Holiday and even Janis Joplin, who, like Jimi Hendrix, Jim Morrison, the Rolling Stones' Brian Jones and Kurt Cobain, also died at 27. "I've never seen any other artist freestyle as if somebody's taking a knife and stabbing their heart," says Winehouse's backing vocalist Zalon Thompson, a close friend. "When she was singing, it was like it was from her diary. It sounds so simple, but she was able to connect. She was a walking truth."
Back to Black was an instant classic, with a startling blend of modern and retro R&B that appealed to a huge cross section of music fans, selling more than 10 million copies worldwide. Its breakthrough single, "Rehab," was to a T: wisecracking, defiant, self-deprecating and somehow hopeful. She never apologized for her personal demons, and with the success of "Rehab," even made them her calling card. She was brazen about the crack, coke and alcohol she abused, and she created chaos wherever she went, from showing up wasted on the British quiz show Never Mind the Buzzcocks to heckling Bono while he accepted an award, yelling, "Shut up! I don't give a fuck!"
When Winehouse was 22, she met Fielder-Civil – a music-video production assistant – at a local bar, and their on-again-off-again relationship seemed to unravel what had already been a fragile personality. Playing gigs became secondary to spending time fussing over her "baby"; their previous breakups had been devastating for Winehouse, inspiring Back to Black's, darkest moments, like "Wake Up Alone," a heartbreak ballad as depressing as its title suggests. "I felt terrible about the way we treated each other," she said after they married. "I thought we'd never see each other again. Now I just want to enjoy myself and spend time with my husband." That plan was derailed: A year later, Fielder-Civil was sentenced to 27 months in jail for assault and bribery charges.
Winehouse grew up in Southgate, in North London, a blue-collar Jewish kid raised on classic pop standards by Frank Sinatra and Dinah Washington. Her parents, Mitch, a cab driver, and Janis, a pharmacist, married in their early twenties and split when Amy was nine. Though she and older brother Alex mostly lived with Janis, Amy considered herself a daddy's girl – a tattoo on her left shoulder even bore the phrase. While we were in Toronto in 2007, Mitch was in town for a couple of days, and Amy clearly loved doting on him, making him a turkey-and-cucumber sandwich that he said reminded him of a matzo-banana combo she used to fix for him. "I was a very silly, very hyper kid," she said at the time.
By age 10, Winehouse had formed a Salt-n-Pepa-inspired rap duo called Sweet 'n Sour with her best friend, and started messing around with Alex's guitar a couple of years later. "When I got a little bit of money, I got my own, so I could play whenever I wanted," she said. "I always wrote poetry and stuff like that, so putting songs together wasn't that spectacular." She showed early promise at the Sylvia Young Theatre School and studied briefly at the esteemed BRIT School for performing arts – the same school Adele later attended – and a few others. She pierced her nose, began smoking pot and skipping class, and dropped out of school when she was 15.
Winehouse started singing with a jazz band when she was 16, and playing solo gigs – just her and her guitar – a few years later. It wasn't long before a friend offered her free studio time to track some demos, but Winehouse was perplexed: "I didn't think it was special to be able to sing," she said. "And I didn't understand that I could go in a studio and pay nothing, and write whatever I wanted to write. I just didn't understand why."
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."
As she planned for a 12-date European tour this spring, Winehouse checked herself into the Priory clinic in London for a "rehab assessment," reportedly at her father's request. The clinic released her just a week later, allowing Winehouse to complete the rest of her treatment as an outpatient so she could go on the road. Her representative released a statement saying that Winehouse was "now looking forward to playing shows around Europe this summer and is raring to go."
"Before she went away, it all seemed fine – she did a gig at [London's] 100 Club, she did a little gig here," confirms the Hawley Arms' Charles-Ridler. "And she seemed really upbeat. The color in her face was a lot better and she seemed to have put on weight, and it was like the old Amy coming back."
But the first show on that tour, at Kalemegdan Park in Belgrade, Serbia, on June 18th, was a disaster. Before an audience of 20,000, a visibly inebriated Winehouse fumbled her lyrics, missed cues and occasionally stopped singing entirely while her backing vocalists carried on. The crowd began booing, and she threw a shoe at them. On June 21st, after footage of the performance went viral, Winehouse's rep announced that the singer was "withdrawing from all scheduled performances," canceling the 11 remaining dates and saying, "Everyone involved wishes to do everything they can to help her return to her best and she will be given as long as it takes for this to happen." Her final public appearance came less than a week before her death, when Winehouse showed up onstage during a Bromfield gig at the London Roundhouse, dancing nearby while her goddaughter sang the Shirelles' "Mama Said." She looked sober but nervous, less like a lioness and more like a little girl.
For fans, one solace is the possibility that there is more music than just the few dozen tracks she released in her lifetime. There are Back to Black outtakes that could eventually see the light of day, and Winehouse was reported to be working with Remi, ?uestlove, Raphael Saadiq and others on a follow-up. When Hoffman visited her for Rolling Stone, Winehouse described what she had in mind: "When the songs are done, they'll be all atmospheric and cool like that. They might be like these girls I've been listening to, like the Shangri-Las."
And she was looking forward to brighter days. Remi says Winehouse was supposed to attend the wedding of her first manager, Nick Shymansky, the day after she died, and that he, Winehouse and Nas were planning to vacation together in Barbados this fall to celebrate the singer and rapper's shared birthday on September 14th. "We'd actually been working on her third album for the last three years – here in London, in Barbados, Jamaica and St. Lucia," Remi says. "We'd talk on Skype regularly for two or three hours at a time. She was better – better than she was three years ago, for sure, and in a different space. She's gone, but what she's done is going to live on forever."
Additional reporting by Patrick Doyle; Monica Herrera; Olly Parker and Courtney Rubin.
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