August 08, 2011 12:00 PM

Not many Grammy winners would bother to sing backup for a kid, but Amy Winehouse would do anything for her goddaughter. On July 20 the Brit hit the London iTunes festival stage with 15-year-old Dionne Bromfield, looking healthy and happy as she clapped, shimmied and sang along to the Shirelles classic “Mama Said.”

It was a small but significant step in the right direction after her last public performance, a disastrous June 18 concert in Belgrade, Serbia, during which Winehouse-who had long struggled with substance abuse-appeared intoxicated, stumbled around onstage and slurred lyrics to her hits. “Up until a couple of months ago, she was doing really well,” says her longtime rep and friend Chris Goodman. “And then she had a step backward and it spiraled.” After the June incident, her European tour was canceled, and she retreated to her London home. “She kind of became a recluse,” a friend says of the ’60s throwback with the soulful voice. “She spent most days at home writing.” On one such day, July 22, Winehouse went to lunch with her mother, Janis, 56; had a doctor’s check-up as part of her addiction treatment program; and played the drums into the night before heading to bed around 10 a.m. July 23.

She would never wake up. A member of her security team found her unresponsive around 4 p.m. London time-just a couple hours after his last check-in when she appeared to be sleeping. Paramedics arrived quickly but pronounced the 27-year-old dead at the scene. “Our family has been left bereft…. She leaves a gaping hole in our lives,” her parents and older brother Alex said in a statement.

Police found no drugs or related paraphernalia in the singer’s home, and toxicology results may take weeks. Contradicting a report that she had gone on a bender before her death, her boyfriend Reg Traviss told The Sun that Winehouse was “full of life and so upbeat recently,” and was busy planning her outfit for a friend’s wedding that weekend. Still, her very public, tumultuous past-in the four years since the release of her Grammy-winning album Back to Black and her defiantly autobiographical anthem “Rehab,” Winehouse’s personal low-lights included multiple hospitalizations, arrests and stints in treatment (see box)-led many to conclude her sudden death was caused, directly or indirectly, by drugs and alcohol. As her distraught mother told The Sunday Mirror, it “was only a matter of time.”

The news of another talented musician gone too soon (linking her to other tragic figures such as Janis Joplin, Kurt Cobain and Jimi Hendrix, who all died at 27) sparked an outpouring of grief. Longtime pal Russell Brand, a recovering addict himself, wrote on his website, “When you love someone who suffers from the disease of addiction you await the phone call. The sincere hope is that the call will be from the addict themselves, telling you they’ve had enough … [Y]ou fear the other call, the sad nocturnal chime from a friend or relative telling you it’s too late, she’s gone.” Sharon Osbourne, whose daughter Kelly was close to the singer, shared a similar sentiment on The Talk, acknowledging that Winehouse-who famously sang, “They tried to make me go to rehab/I said, no, no, no”-didn’t get help because “she didn’t want it.”

While the British tabloids delighted in portraying Winehouse (whom they dubbed “Wino”) as a reckless mess, those who knew her say she was much more than a party girl. Friends say beneath the disheveled beehive and heavy eyeliner was a slyly hilarious potty mouth who loved to cook Jamaican curry or her grandma’s chicken soup for friends. “She never took herself too seriously,” says Sarah Hurley, landlady of the Good Mixer, one of Winehouse’s favorite pubs. “Amy was a sparkly character who made a lot of friends in the bar.” Or wherever she went: On an extended vacation in St. Lucia in 2009, she put on impromptu shows for fellow tourists and grew close to locals such as bar owner Marjorie Lambert. “She’d make everybody happy,” says Lambert, adding that Winehouse bought drinks and food for patrons and paid for 20 kids to go horseback riding. She also befriended local Jacob Jn. Baptiste and gave him $6,000 when he needed a hernia operation. “She was down-to-earth,” he says, recalling karaoke sessions with the star.

Winehouse also leaves behind a grieving family who publicly tried to save her. In 2007-while she was swept up in a destructive, drug-fueled marriage to Blake Fielder-Civil, 32-her mother begged her to get help, writing in an open letter in the U.K.’s News of the World, “Early fame has overwhelmed you, it’s dizzied you and muddled your mind… I want you back, and I’ll make you fitter and stronger.” Her pleas went unanswered. In a subsequent interview Janis said, “I’ve steeled myself to ask her what ground she wants to be buried in, which cemetery.”

Winehouse’s lifestyle seemed tamer the past two years-in part, thanks to the influence of Traviss. Recently, she was “exercising everyday and doing yoga,” the film director, 33, told The Sun. In May, after an intervention by her father, Mitch, 60, she checked into rehab to prep for her tour. But “she bought a mini bottle of vodka on the way to rehab in typical Amy style,” says the family friend; her stint only lasted a few days. Years of abusing her body also took a toll on her health, but she seemed not to care. “She suffered from emphysema,” says a pal, “but she still drank and smoked heavily-at one point two packs a day.”

The singer grew up with her brother in the Southgate section of North London, in a middle-class home filled with the music of Frank Sinatra and Ella Fitzgerald. When she was 9, her dad, a cab driver, and mom, a pharmacist, split up. Winehouse won a scholarship to the Sylvia Young Theatre School at 12 but left partly due to bad grades. “When she wasn’t singing she was naughty,” Young wrote in the Daily Mail in 2007. “The misdemeanors were never serious, but they were persistent.”

Soon afterward, her transformation into a tattooed rebel began-as did eating disorders, cutting and drug abuse. She once boasted that she spent hundreds of dollars a week on pot. “My parents realized that I would do whatever I wanted,” Winehouse told the Sunday Times in 2007. Surprisingly, her self-destructive tendencies didn’t get in the way of her gifts back then. “She’d just sit in the corner smoking competitively,” said Bill Ashton, the director of England’s National Youth Jazz Orchestra who worked with her in 2000, “then come into the room and nail every song.”

As much as her talent brought her fame and fortune, Winehouse had other aspirations; she often spoke longingly of being a mom. At her funeral July 26, Mitch said, “Amy was very much looking forward to her future with Reg.” But having a family of her own was something she’d sadly never attain. Says a pal: “She just wanted a normal life.”

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