With a gorgeously singular voice that exposed both the pain and perseverance of her tumultuous life, she became a near-instant icon. In the end, substance abuse overtook her considerable talent, and her demons got the best of her. EW remembers an artist gone too soon at 27

By Melissa Maerz
July 29, 2011 at 04:00 AM EDT

Perhaps no one was entirely surprised when Amy Winehouse was found dead in her London apartment on July 23. During her short, meteoric career, the retro-soul star with the sweeping eyeliner and dramatic beehive hairdo earned as much attention for her battles with drugs and alcohol as she did for her achingly raw singing style. But it stung nonetheless to witness the abrupt end of a talent whose Grammy-sweeping breakthrough Back to Black was a testament to living on her own terms — even when she sang that she ”died a hundred times” for love. Her strikingly husky voice and natural musicality, drawn equally from classic torch singers, ’60s girl groups, and hip-hop bravado, delivered an emotional honesty missing from America’s plastic pop landscape.

By the time of her death, sadly, it had been a while since Winehouse made headlines for her music and not substance abuse and self-harm. Her final years were marked by erraticism and mystery — and her passing raises even more questions. A preliminary autopsy was inconclusive, and an official cause of death won’t be released for another one to three weeks, pending further toxicology tests. Divorced two years from longtime love Blake Fielder-Civil, 29, she left behind her parents, an older brother, a boyfriend (director Reg Traviss), and an estate estimated to be worth as much as $30 million, but it’s unclear how it will be divided. And though there were numerous reports that she had been in the recording studio, a long-in-the-works follow-up to Black had yet to materialize.

The fact that Winehouse died at 27, like Kurt Cobain, Janis Joplin, and Jimi Hendrix before her, made her a member of a legendary if singularly unlucky club. Some were quick to say that her icon status can’t match the others’; after all, she released only two albums in her lifetime, just one of them a bona fide hit. Nevertheless, immediately following her death, Back to Black shot to No. 1 on iTunes and swiftly climbed the Billboard album chart, and admirers ranging from Tony Bennett to Kelly Clarkson mourned her in an outpouring of online affection. ”Amy changed pop music forever,” Lady Gaga wrote on Twitter. ”I remember knowing there was hope, and feeling not alone because of her. She lived jazz, she lived the blues.”

Before her very public, very tragic downfall, there was lightness, too. Charles Moriarty, who shot the album cover of Winehouse’s critically acclaimed 2003 debut, Frank, recalls some ”fun, silly” times photographing her in both London and New York City. ”She was amazing,” he tells EW. ”You knew right away she was going to be a big talent. She was quite a petite girl and when that mouth opened, a lot came out of it.” That was certainly the case with Back to Black, released to U.S. audiences in March 2007, which established her as a global superstar just as she began to self-destruct. The single ”Rehab,” with its ”No no no” refrain, became her calling card and ultimately her epitaph — but at the time, it felt like the perfect anthem for the anti-recovery age: a defiant middle finger to sobriety that peaked at No. 9 on the Billboard Hot 100. With its help, Back to Black sold 10 million copies worldwide and netted Winehouse five Grammys at the 2008 ceremony, including Record of the Year and Song of the Year, though she was forced to accept her awards via satellite due to visa troubles.

Winehouse herself told EW in 2007 that Black came from a dark place: ”The songs I wrote on the album are from times when I was so messed up in the head,” she admitted. Calling herself ”clinically depressed,” she said that she listened to old records in order to channel her despair over her relationship with music-video assistant and high school dropout Blake Fielder-Civil into something meaningful.

”The Shangri-Las were teenage girls who would lie in the road for their boyfriends,” she said, speaking of one of her favorite inspirations, the bouffanted foursome who warbled 1960s classics like ”Leader of the Pack.” The message behind many of their songs — ”My life has no purpose if I don’t have my boy” — was one she understood well.

Sadly, those words would prove somewhat prophetic for Winehouse. Not long after Black‘s release, she married Fielder-Civil in a courthouse in Miami (blowing off a Rolling Stone reporter to do so) and seemed eager to start working on her next record. But six months later, Fielder-Civil was arrested and then sentenced to 27 months in jail for assault and obstruction of justice. Distraught over his incarceration, Winehouse grew increasingly unstable. Paparazzi were more than happy to capture her wandering through the streets half-dressed or with strange marks on her arms. A video even surfaced in which she appeared to be smoking crack cocaine. Since 2007, there had been five arrests for drug possession or assault, various hospitalizations, and multiple stays in rehab.

By May 2008, Black producer Mark Ronson announced that the singer was ”not ready to work on music yet.” Months later, she split from Fielder-Civil and began spending large amounts of time in the Caribbean, which she reportedly said helped her stay clean. Promisingly, she booked a number of summer 2011 festival gigs in Europe, but at a June performance in Belgrade, Serbia, in front of 20,000 fans, she was shambolic and nearly incoherent. A video posted to YouTube shows her slurring lyrics, stumbling across the stage, and taking off her shoe and throwing it. Footage of the performance quickly went viral, and Winehouse’s spokesman announced that she was ”withdrawing from all scheduled performances,” adding that ”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.” As recently as early July, veteran crooner Tony Bennett, who recorded a track with Winehouse for his forthcoming album of duets, told The Guardian, ”I’m worried about her and I’m praying for her.”

Winehouse told EW that she would always have new material to draw from; her life, she said, would never be ”butterflies and sunsets.” As her friend, actor Russell Brand, wrote after her passing, ”When you love someone who suffers from the disease of addiction you await the phone call. There will be a phone call. The sincere hope is that the call will be from the addict themselves, telling you that they’ve had enough, that they’re ready to stop, ready to try something new. Of course though, you fear the other call, the sad nocturnal chime from a friend or relative telling you it’s too late, she’s gone…. We have lost a beautiful and talented woman to this disease.”

…As Remembered By Her Famous Fans
”A voice that was filled with such power and pain that it was at once entirely human yet laced with the divine.”
—Russell Brand

”Kurt Cobain, Janis Joplin, Jim Morrison, Jimi Hendrix and now Amy Winehouse. All died aged 27. RIP to you all.”
—Outkast’s Big Boi

”I am truly devastated that her exceptional talent has come to such an early end…. It had been my sincere hope that she would be able to overcome the issues she was battling.”
—Tony Bennett

”Amy paved the way for artists like me and made people excited about British music again whilst being fearlessly hilarious and blasé about the whole thing.”

(Additional reporting by Kyle Anderson and Leah Greenblatt)

An Amy Playlist: Her 10 Best Songs
1. ”You Know I’m Not Good”
”Rehab” may be her signature song, but ”No Good” had every one of the elements that made a Winehouse song great: pain and pathos delivered with aching, tough-girl verve; unforgettable imagery (”You say, ‘What did you do with him today?’/And sniff me out like I was Tanqueray”); a soul melody so timeless it could have been cribbed from Donny Hathaway’s diary; and, of course, that unmistakable voice.

2. ”Rehab”
She said ”No no no,” and suddenly the world said ”Yes” to a new superstar. The song that took her from U.K. upstart to global phenomenon got there with the Dap-Kings’ horn blasts, a rolling backbeat, and her musical refusal, as always, to do what anyone else wanted her to do.

3. ”Valerie”
Original artists the Zutons sang it just fine, but when Back to Black producer Mark Ronson asked Amy to take on the song for his 2007 solo album Version, she turned a fairly standard midtempo rock plea into a rollicking dance-floor dazzler.

4. ”Tears Dry On Their Own”
A sweetly soulful chin-up to a doomed love affair in which Amy, battered by romance but never beaten, sings herself back to fighting form with snap-crackle musicality and a lilting, tomorrow-is-another-day vocal hook.

5. ”F— Me Pumps”
Long before American audiences began paying attention, Winehouse sharpened her storytelling chops with this perfectly sly snapshot of aimless ‘n’ shameless blotto youth.

6. ”Back To Black”
Amy unleashes her best Sarah Vaughan on this almost dirgelike ballad, a moody, deliberately slow-build spiral into beautiful despair.

7. ”Love Is A Losing Game”
Nobody did bittersweet requiems for romance quite like her. As stately strings and prettily plodding piano unfurl like cigarette smoke, Winehouse croons a woeful farewell to one unforgettable paramour — though you knew she was never really done with love for long.

8. ”Me & Mr. Jones”
”What kind of f—ery is this?” With that immortal line, Amy dispatched one unlucky fellow (hip-hop’s Nas, born Nasir Jones, claimed in an interview to be the titular subject) with singular NSFW aplomb.

9. ”Amy Amy Amy”
Winehouse, nearly immobilized with lust, is at her most sultry on this slow-winding dirty daydream of a song — baby-making music at its speakeasy-slinking best.

10. ”In My Bed”
Over soul-jazz atmospherics and a rumbling melody that vaguely recalls Portishead’s ”Sour Times,” Amy recognizes an old love for the lost cause he is; in other words, she knows he’s no good.