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."
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