Razor sharp, Winehouse changed the music scene for ever

There's no point seeking someone to blame – Winehouse's extraordinary insecurity lay at the heart of her troubles. Sophie Heawood recalls a difficult, funny, gifted and charming woman

It is hard to believe, as I type these words, in a state of shock, at Saturday teatime, that Amy Winehouse is dead. Yes, it was something people had speculated upon for some time. Yes, you might even suggest that if somebody takes that many hard drugs, drinks that much liquor and punishes their young flimsy body to that extent, death is not so much a tragedy as an inevitability. You can even point out that, at 27, Amy's death puts her in the morbid hall of rock'n'roll deaths about which conspiracy theorists love to ponder. Janis Joplin, Kurt Cobain, Jimi Hendrix and Jim Morrison all destroyed themselves at the same point in their lives – something that Cobain's mother described, after her son's passing, as "joining that stupid club".

But the death of Amy Winehouse was not inevitable, and it is pretty hard not to think of it as tragic. Keith Richards has lived through such physical self-destruction to tell the tale. And so we hoped, hoped desperately, that Winehouse would too. I met her on several occasions, interviewed her, followed her career avidly, played her songs so many times I knew the lyrics backwards. Surprisingly, the tabloid reports were not unduly sensationalist – she really was that much of a mess. But she was also hysterically funny, with a razor-sharp London wit and a shocking line in politically incorrect putdowns and deadpan one-liners.

She was sharp; had a way with words, as well as song. And, oh boy, the songs – the accolades, the awards and the artistic attention was all justified too. Back to Black, her second album, with its six Grammy nominations and five wins when she was only 24, changed the music scene for ever, with its lyrical musings on cold, dead broken hearts, illicit sex, and chips and pitta and gin. Songs such as "You Know I'm No Good," and "Love is a Losing Game" provide as good an insight into Amy Winehouse's life as any biography could offer.

One thing must be made clear – while everybody seeks to find somebody to blame – it just isn't true that nobody offered her the help she needed in beating her addictions and her demons. God knows, people tried – her record label, other pop stars, people who had been through it and come out the other side. She just couldn't quite accept it. Her biggest hit, the endlessly catchy song "Rehab", was not just a bunch of fun rhyming lyrics. When she sang "They tried to make me go to Rehab, and I said no, no, no," in a chorus that sold a million records, she meant it – and that was written before her biggest successes and her worst excesses had even begun. There were many subsequent attempts to quit herself of drugs and booze for ever. She tried in the UK, she tried overseas. Her stays in these places never lasted long, because Winehouse's real problem was self-belief, an insecurity only compounded by the extraordinary worldwide success of Back to Black, which left her less sure of herself than ever before.

Far from surrounding herself with sychophants, as so many stars do, Winehouse dealt with success by surrounding herself with thoughts that brought her down and people who brought her downers. Something in her nature was so macho and so cocky, and yet so self-effacing, that she could never quite enjoy the compliment, or sit back and say, yeah, I've done pretty well, good for me. Mark Ronson, the producer responsible for bringing out so many of the great moments on Back to Black, told me this when I interviewed him:

"I introduced Amy to my mum, having just told mum that Amy's album had gone platinum that same day. So my mum later introduced Amy to somebody else and said, 'This is Amy, her album went platinum!" I was like SHUT UP! If you tell everyone in front of Amy she'll basically shrivel up and go into a shell and not come out. She doesn't want to be lavished. She doesn't want people gushing over her. She just can't get anything out of it – even on the day her own album goes platinum."

Ronson also spoke about how they made a lot of the album together: "She wrote all those songs, apart from 'Back to Black', which we wrote together. Each day she'd come in and play me a song on her acoustic guitar, show me what the chords were, and leave. I would work through the night, strip the chords down, see what could be arranged. She'd start with a shuffly '40s blues standard and I'd try and make it into an old-school '60s thing. But 'Rehab' wasn't a song initially, it was just a conversation. She was telling me quite a sad, personal story about when she got really fucked up and her dad wanted her to get help, but she was trying not to make the story too heavy when she told me, so she said, 'Oh, they tried to make me go to rehab but I was like [adopts comedy booming voice] no, no, no.' It was so funny, the way she said it. I was like, that could really be a song you know."

Winehouse always wanted to make things fun – a friend of mine once got into a cab whose driver had just taken Amy somewhere. "He said that he'd been chatting to her in the cab and he'd told her it was his daughter's birthday that day and she was a fan of hers. Amy says, ''Ere, let me out, I need to get fags,' so he stops and she pops to the newsagents and comes back with 40 fags and a newsagent-style birthday card which she unwraps and writes for his little girl."

On one occasion when we met, Winehouse was backstage at Sharon Osbourne's daytime TV show, supposedly preparing to sing. Of course, what she was really doing was getting wasted and making everybody laugh. She kept demanding vodka, but a runner, clearly unsure if he should really get her it or not, kept fudging the task in hand, causing Amy to mutter that "inside his head, there's two monkeys rubbing a stick together". Everyone cackled as she held court. While the vodka failed to appear, she kept herself amused by constructing an elaborate hoax to convince one of her band members that we had eaten all of his Ferrero Rochers, making us all go along with the joke, when in fact they were hidden under the sofa. In print, it may not sound very funny, but in the flesh, when led by the cunning, cockney-barmaid style Amy, it was hysterical.

Blake Fielder-Civil was with her, and she and he would take it in turns to disappear to the toilets. She asked him if he had received "those filthy text messages I sent you".

She asked her manager, a huge, burly man called Ray, for cash, telling him she had none. He gave her a couple of hundred quid and asked her which songs she would sing at a show for Russian bankers which she was doing to make money on the side. While doing something else entirely, with her back to him, she reeled off a five-song setlist with precision, based on which songs it was easier to have people talk through. "They love me, those Russians, but they don't listen to a word I sing," she said.

After she told me she had tried rehab and found it wasn't to her liking, I asked her what she thought people went to the Priory for. "To get crack, obviously!" she said, grinning. I asked her if she was fond of her vices. She stopped to think about that, clearly amused. "That's a good one. Do you mean, do I like the things that make me fuck up? Definitely. I feel very attached to my vices. Alcohol, prostitutes – oh, I don't know ..." She said if she weren't a musician she'd be a beautician, giving women bikini waxes, because they made so many men so happy. She wanted to get married in Las Vegas and see the dancing girls there but not to go gambling. Why not? Her voice hushed to a murmur: "Because I'm not very lucky." (That same baby voice came out again when I rang her in the summer of 2007, to see if her string of cancelled concerts meant she wouldn't meet her Glastonbury commitment. "I just want to sing my songs," she mumbled pathetically.)

"You're a very naughty girl, aren't you?" asked Sharon Osbourne, when she entered the room. Again, Amy did the little-girl-lost act, the mumbled confusion, what could Sharon mean?

Yet Amy's self-awareness was acute. Back in her garrulous, raconteur mode, she told me later that she was a violent, terrible drunk, that since meeting Blake she had drunk every single day, that she was living a double life by cheating on her then boyfriend with Blake. She admitted to eating disorders and an addictive personality, that she was even addicted to the rowing machine at the gym, and that she ended every day by having sex. No subject was off-limits. She even suggested that she and I could make a fitness video together.

When she was a guest on TV programmes such as Never Mind the Buzzcocks, or Russell Brand shows, where clever men usually outwit each other and female guests can sometimes struggle to be heard, she was on form, even when being teased about her hair, her boyfriend, her tabloid antics. When asked if she'd like to work with Katie Melua, she replied neatly "I'd rather have cat Aids, thank you."

What struck me on spending time with her was how she would focus on the negative, on something to insult herself with. Wittily, yes, but the darkness was evident. At one of our meetings I had recently come back from a visit to Israel and asked her something, perhaps with naive enthusiasm on my part, about growing up Jewish. "Yeah," she said, begrudgingly, "I'm a dirty little Jew." There always had to be a stain on the glass; something floating in the water. Nothing was clean. Her fingernails were dirty, her armpits were stubbly, her knees were knobbly. And we loved her for it – such a relief after so many clean pop princesses. Amy Winehouse and Lily Allen were an enormous breath of fresh air precisely because they did talk about drugs, they did talk about battling with their bodies, about what it was like growing up in London. They were the opposite of Disney princesses, or well-briefed stars whose interviews consist of declarations of how blessed they are and how they're just lucky to have this opportunity to perform for their growing fanbase.

It's not that Amy and Lily weren't briefed – they just didn't care. Their messy honesty, along with the brilliant songs, was what drew us in. And they both found success too much for them. But whereas Lily has, for now, dealt with her fame overload by retiring from being a pop star, getting married to a nice, normal bloke, starting a family and going to village cricket matches near her home in the Cotswolds, Amy couldn't find that safe way out. There will be people who blame the family, who blame her ex-husband, who blame the music industry. But in the end, the only person who could have cleaned up her act was Amy herself.

It is a tragedy.

The musicians’ musician, so admired by her peers

In the end, long after people have stopped telling stories of drink and excess, they will talk about Amy Winehouse's voice and her music.

Some of the world's best-known musicians last night paid tributes, determined that her back catalogue of hits and unforgettable live performances would not be forgotten. Crooner Tony Bennett, who performed on stage with Winehouse, said: "She was an extraordinary musician with a rare intuition as a vocalist. I am truly devastated that her exceptional talent has come to such an early end."

Mark Ronson, who worked closely with her, added: "She was my musical soulmate and like a sister to me. This is one of the saddest days of my life." The Simply Red singer, Mick Hucknall, said she was "the finest female singer Britain has produced by a long way."

Winehouse herself considered music a serious business and could be scathing about those she felt were doing it a disservice. Dido was dismissed as "background music", while Kylie Minogue was "not an artist, she's a pony".

The music critic John Aizlewood attributed her transatlantic success to her genuinely original sound. "A lot of British bands fail in America because they give America something Americans do better," he said. "But they won't have come across anything quite like Amy Winehouse."

The gifted performers who also died at 27

Amy Winehouse is the latest member to join a tragic rock institution known as the "27 club" – musicians with a weakness for drink and/or drugs who have died at 27 and achieved notoriety as a result.

Robert Johnson, 16 August 1938

Known as king of the blues to some, and the grandfather of rock'n'roll to others. Died after drinking whiskey laced with strychnine.

Brian Jones, 3 July 1969

The Rolling Stones' guitarist was found drowned in his swimming pool. Some claimed suicide, others murder. The coroner: "death by misadventure".

Jimi Hendrix, 18 September 1970

One of the greatest electric guitarists. Choked to death on his vomit after bingeing on red wine and taking sleeping pills.

Janis Joplin, 4 October 1970

Lead vocalist and songwriter for Big Brother and the Holding Company, the Kozmic Blues Band and Full Tilt Boogie Band. She died of a heroin overdose combined with excessive amounts of alcohol.

Jim Morrison, 3 July 1971

Lead singer in the Doors. Morrison mistook heroin for cocaine and suffered an overdose that triggered the heart failure given as the official cause of death.

Kurt Cobain, 5 April 1994

Lead singer in Nirvana. Found dead at home with a shotgun wound to the head, after apparently taking his own life.