Sam Smith, Mark Ronson and More on Amy Winehouse's Lasting Legacy, Tragic End and Eye-Opening New Documentary

Winehouse's former bandleader recalls his last conversation with the singer: "She said, 'I’ve been watching videos of myself on YouTube, and I can sing.' ... There had been doubts, but for her to realize that was one of the nicest things she could possibly say."

One day in November 2005, Amy Winehouse sat in a car with her friend and co-manager Nick Shymansky, winding through the English countryside toward a rehab center. The singer’s drinking had been getting out of control, Shymansky remembers, and he felt she needed help. When they arrived, Winehouse said she would check in on one condition: that her father, Mitch, agreed. So they drove 50 miles to Mitch’s house, where Winehouse perched on her father’s lap and asked, "Do you think I need to go to rehab?" Mitch’s reply? "Absolutely not."

Four months later, Winehouse was recording with producer Mark Ronson in New York. Ronson found her account of the incident so funny that he suggested she turn it into a song. Three hours later, she had written her breakout hit, "Rehab." "If I’d known all the stuff that was going on, I don’t know if I would have thought it was so amusing," Ronson tells Billboard today. "But she said it in such a light way." Says Shymansky: "My dream for Amy was that she could be the best and biggest artist in the world. The irony is the song that got her there was a cry for help."

Winehouse died from alcohol poisoning on July 23, 2011 at the age of 27. Her short, tumultuous life is the subject of a riveting new documentary, Amy, by director Asif Kapadia and producer James Gay-Rees, the team behind 2010’s award-winning Senna. When Amy premiered at the Cannes Film Festival in May, The Guardian hailed it as a "tragic masterpiece."

In Winehouse’s story, many of the perils of 21st-century fame collide. She was hounded not only by paparazzi — the famously aggressive British tabloids painstakingly tracked her movements around her London home — but by talking heads insensitive to addiction and mental-health issues. One disturbing sequence in the film shows Winehouse as a punchline for talk-show hosts. "She was ill. You had people who had praised her and now they were murdering her," says Darcus Beese, president of Island Records and Winehouse’s former A&R man. "Hopefully, when they see their faces on the screen they’ll feel embarrassed."

As different as she was from Britney Spears, another singer classified as a "train wreck" at that time, Winehouse felt the first lashes of 24-7 gossip coverage as it converged with her celebrity. And that wasn’t all Winehouse contended with: The pressure to be thin worsened her existing eating disorders, and the eventual onset of stage fright only seemed to increase her dependence on alcohol — problems that plagued her until the end of her life, even after she had broken free from hard drugs. "The film was an eye-opener," says Beese. "I didn’t realize we were signing a girl who was broken."

The documentary, which opens July 3 in the United States, looks to do what Winehouse could not in her brief career: secure her legacy. She had no gift for self-promotion. Her extra­ordinary talent resided entirely in her voice and songs. "We have this stereotype of young Mozart," says Ronson. "Lightning strikes his head and then he furiously ­scribbles for two hours and has a concerto. She’s the only person I saw who was ­actually like that."

By infusing a retro sound with a ­bracingly modern sensibility, Winehouse opened the door for singers like Adele and Sam Smith. In kickstarting Ronson’s career, she also helped make "Uptown Funk!" — Ronson’s hit with Bruno Mars, the longest-leading Billboard Hot 100 No. 1 of this decade — possible. "Her song 'You Sent Me Flying' is the reason why I sing," Smith tells Billboard. "At 11 years old I was belting out 'F— Me Pumps' and soaking in all the language and honesty."

Yet Winehouse’s stature remains ­uncertain: She’s neither an icon like Kurt Cobain nor a cult figure like Jeff Buckley. Her 2006 album Back to Black has sold 2.9 million copies in the United States, according to Nielsen Music; won five Grammys; and made her a global star. But she played only a few dozen live shows and never chronicled her subsequent struggles in song. While her music remains ­popular — she sold more than 400,000 song downloads in 2014, and "Rehab" has been streamed more than 35 million times on Spotify — Winehouse herself is only dimly understood.

"She never spent enough time [in the United States] for people to get a sense of her outside of being drunk and sloppy," says Republic Records chairman/CEO Monte Lipman. David Joseph, ­chairman/CEO of Universal Music U.K. and an executive producer on Amy, says, "Some asked, 'Are you making a film about a drug addict?' People didn’t even realize she wrote her own lyrics."

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The film is a riveting collage of audio interviews and mostly unseen footage. It took the filmmakers two years to win the trust of Winehouse’s friends, many of whom hadn’t spoken publicly since her death. "At the beginning nobody wanted to talk to me," says Kapadia. "Then ­everybody did." Only Mitch Winehouse has since ­criticized the project, calling it "unbalanced." Gay-Rees says that the initial three-hour cut was "too painful to watch." Even the final 128-minute ­version is ­overwhelmingly sad. Says Shymansky: "You see this happy, witty spark of an artist and then this ­desperately high, lost, ­overexposed, ­overharassed wreck of a person."

Across the street from 30 Camden Square, where Winehouse died, a tree serves as an informal shrine, garlanded with wilting bouquets and heartfelt messages. Nearby, fans can also find the apartment where she wrote Back to Black; the pub where she met her husband, Blake Fielder-Civil; and a lifesize bronze statue unveiled in 2014. The north London neighborhood of Camden Town is where Winehouse became a superstar, an addict, a tabloid obsession and a fatality. "The question was, how did this happen?" says Kapadia. "This didn’t happen in the ’60s. It happened right here, in front of our eyes."

In Amy’s first section, the young Winehouse comes across as a force of nature, opinionated and hilarious. Beneath the surface, however, there were already fault lines. In the film, Winehouse traces her teenage struggles, marked by bulimia, antidepressants and daily weed smoking, to her parents’ divorce when she was 9.

But as traumatic as the divorce may have been — and as tempting as it is to lay blame with a father who downplayed her addictions — Winehouse’s fatal flaw may have been attempting the leap from a normal, if turbulent, adolescence to inhabiting the role of a fearless, risk-­anything artist. "She wanted attention and recognition, but it didn’t really fit her," says Shymansky. "She was making herself into a cartoon," writer Caitlin Moran suggests. "She wanted to look like her music. As a feminist, I hated her getting skinny and showing that tiny stomach off. But there’s an odd empowerment in that, for women — that your only nemesis is you."

In 1999, Winehouse’s friend Tyler James gave her demo tape to Shymansky, a junior employee at production company 19 Entertainment. With his boss Nick Godwyn, Shymansky hooked up Winehouse with Salaam Remi, a rap producer known for his work with Nas and The Fugees. "Amy was confident and witty," says Remi. "In the first 10 minutes she probably had 10 quick things to say, so I’d say, 'OK, we’re putting all that into a song.' "

Island signed Winehouse in 2002. "She was exactly how I thought an authentic artist should be," says Lucian Grainge, chairman/CEO of Universal Music Group. (Grainge, who is also Shymansky’s uncle, was chairman of Universal Music U.K. at the time.) "When she liked you, she was either utterly irreverent or made you feel like the most important person in the world."

Winehouse became a minor star in Britain when she released her jazz-­influenced debut album, Frank, in 2003. "Amy changed the game," says British singer Jess Glynne. "There wasn’t one female artist at the time who was being so brave." But as Frank’s promotional cycle wound down at the end of 2004, "a lot of issues started to come through," says Shymansky. Winehouse became adrift, unable to write. When she met Fielder-Civil, a roguish Camden scenester, "everything started plummeting downhill," recalls Shymansky. "By 2005 she had a stammer. It was awful what was going on with her." One ­executive refers to Fielder-Civil as "that clown she married," but the film — although it only shows him in existing footage — paints a more nuanced picture. "Blake’s no angel, but he’s not the son of Satan either," says Gay-Rees. "Amy would probably have moved in that direction with or without him." (Fielder-Civil, now a father of two, recently said he has been sober for a year, and that it’s unfair to blame him for the death of Winehouse, with whom he’s still "in love.")

In 2005, Winehouse began a drastic ­physical transformation into an emaciated, early-’60s bad girl, complete with ­beehive and tattoos. This striking image — a punk-rock descendent of The Shangri-Las — would boost her celebrity, and ­eventually become a caricature. Her diminished ­physique also revealed that her eating disorder had resurfaced. Says James, "It’s almost like the press telling her she was curvy made her want to be super-thin." Beese remembers seeing her in the street one day: "I could not believe how thin she’d got. I was shocked." When Fielder-Civil broke off their affair and returned to his girlfriend, the emotional trauma uncorked Back to Black. "I write songs because I’m f—ed in the head and need to get something good out of something bad," Winehouse later told Spin.

"She was nocturnal," says James. "When I’d get into bed Amy would be downstairs on the kitchen floor with a bottle of vodka, her guitar and a pen. I would always know when Amy was really down because she’d listen to [The Shangri-Las’] 'I Can Never Go Home Anymore.' "

Winehouse sobered up to record her new songs with Remi in Miami and Ronson in New York. Phil Spector’s teenage melo­­dramas were a touchstone. "It was boyfriend-girlfriend drama to an infinite level," says Ronson. "That’s what her and Blake had." Another point of ­reference: hip-hop, with its swagger and lyrical dexterity. "She learned how to keep the urgency and edginess lyrically, regardless of whether she was using a 50-year-old reference," says Remi. "She didn’t sing like an old jazz singer. She still had the bite of a 19-year-old."

Back to Black was an artistic and ­commercial triumph, but could have been even bigger if Winehouse hadn’t blown off countless opportunities, including two offers from Saturday Night Live. She craved only Blake and ­oblivion: When the couple married in May 2007, they were taking heroin and crack together. In April 2008, she strained her relationship with Ronson when she failed, after five days of work with him, to complete a James Bond theme song for Quantum of Solace, wasting another prestigious opportunity. Remi managed to coax the doo-wop-influenced "Between the Cheats" from her — the last new song she would ever complete. "She had more of a brother-sister relationship with [Ronson]," says Remi. "She’d fight with him over whatever. I said, 'She can’t record? Yes, she can. He just doesn’t know how to record her.' "

If life with Fielder-Civil was unhealthy, then life without him was even worse. Winehouse’s messy festival dates after he was jailed for assault of a pub owner in July 2008 marked a new low. "Once Blake went down she started to fall out of love with music," says Dale Davis, her former bandleader. "In the early days she’d have music on all the time, always be singing. But after that the music stopped."

In January 2008, at Grainge’s behest, Winehouse’s ­doctors drew up an official ultimatum that both she and Grainge signed: Unless she cleaned up, she wouldn’t be allowed to perform or record. After one serious relapse, Winehouse quit drugs for good about a year later — although not with the aid of rehab. An extended stay in St. Lucia starting around January 2009 seemed to help her break from the past; Fielder-Civil filed for divorce during that time, although the two continued to see each other even after the marriage officially ended. "We’d talk about the really messed-up times," says James, ­himself a recovered addict. "Amy would say, 'Do you remember I used to be a crackhead? What was that all about?' "

But she continued to drink too much and eat too little, and the press still hounded her. "It was horrible," says James, her roommate at the time. "We had paparazzi outside our house for years." By 2011 Winehouse’s recovery remained fragile. Her first shows since 2008, in Brazil, went well, but as her summer festival dates approached she began drinking again. Raye Cosbert, originally her tour manager, had by then replaced Shymansky as her overall ­manager; the film shows how the pressure to perform contributed to Winehouse’s unraveling. "She drank because of the fear" of going onstage, says Shymansky, who remained her friend. At her final concert, in Belgrade, Serbia, on June 18, she imploded, stumbling silently while the crowd demanded, "Sing!"

"There was a huge chain of selfishness and negligence around Amy," says Shymansky. "I remember an expert saying on the news that she could drop dead at any minute. But there were still gigs being booked. I would never have anything to do professionally with someone in that state." Says Davis: "The finger can be pointed at certain people, but in many respects we can all be blamed. I’ve gone through all those feelings myself. I would have had to be there 24 hours a day to try and help."

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A few hours before she died, Winehouse spoke to Davis on Skype. "She said, 'I’ve been ­watching videos of myself on YouTube, and I can sing,' " he recalls. "And I said, 'Of course you can sing!' There had been doubts, but for her to realize that was one of the nicest things she could possibly say."

At 3 p.m. the next day, July 23, her bodyguard Andrew Morris found Winehouse in bed. She had died during the night. Ronson, Remi, her parents and her friend Kelly Osbourne were all among the several hundred mourners at her funeral (a number of her close friends were already in London to attend Shymansky’s wedding). Fans gathered on the day of her services by her home, leaving flowers and candles in a makeshift memorial. Admirers from Lady Gaga ( "Amy changed pop music forever") to Winehouse’s old friend Russell Brand ("We have lost a beautiful, talented woman") paid tribute online. Even the tabloid headlines announcing her death were muted.

Remi gave the filmmakers a recording of Wine­house reciting the lyrics to an unreleased song called "You Always Hurt the Ones You Love"; it’s evidence that her songwriting talent endured. She had talked about starting a jazz/hip-hop project with Questlove, Raphael Saadiq and Mos Def, perhaps as a way of sidestepping the ­pressure to match Back to Black. But she also had a third album mapped out, and studio time booked with Ronson and Remi for later in 2011.

"She probably finished the writing ­process a few weeks before she passed," says Remi, who was en route to her house when he got a call saying she had died. "As far as I could see, we had 14 songs. Whatever needed to happen, it was right there."

But Universal will never release any of the demos, because Joseph destroyed them. "It was a moral thing," he says. "Taking a stem or a vocal is not ­something that would ever happen on my watch. It now can’t happen on anyone else’s." It’s likely that the 2011 outtakes collection Lioness will remain Winehouse’s final release: a fragmented coda to an abbreviated life.

Mitch, who has been remarried since 1996, started the Amy Winehouse Foundation, which bene­fits addiction causes, after the singer’s death; her mother, Janis, donated the proceeds of a 2014 memoir to the foundation. (Winehouse didn’t create a will, so her parents inherited her $4.6 million estate.) "We made many mistakes," said Mitch recently, "but not loving our daughter was not one of them."

At one point during Winehouse’s struggles, Grainge staged a sort of intervention with her in his office. "She was actually famous for being bloodied, walking down the street unkempt. I had dozens of articles photocopied, to show the impact of her notoriety ... it was from a position of tough love," he recalls. "She sat on the end of my desk with this tiny miniskirt on and picked up this ­enormous ­acoustic ­guitar. She played me songs that were ­obviously about ­relationships, and I ­remember the tears running down her face, and mascara everywhere." All she ever wanted to be famous for, Grainge ­remembers, was her songs.

This article originally appeared on Billboard.com.

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