Chapter 1The Jazz Singer's Granddaughter

Foreword

I came to Amy Winehouse by accident, and through the back door of someone else's story.

I had been working, at the time, on a woman of the midcentury — one of the studio-trained voices of the 1950s, dead for decades — and I had a record playing in the next room while I made tea. Except it was not her record. It was a newer one, put on by someone else in the house, and the phrase that stopped me halfway across the kitchen was a phrase I thought I already owned. The vowel held a half-second past its welcome. The line bent downward at its end and landed a quarter-tone flatter than the ear had been promised, so that the note arrived as a small disappointment the body registers as feeling. I knew that gesture. I had spent the better part of thirty years listening to the women who invented it. What I did not know was how it had found its way into a record made in 2006 by a girl from Southgate who had not been born when the last of those women died.

The record was Back to Black. The girl was twenty-two when she made it. And the voice coming out of her was, by every measure I could bring to it, older than she was — older, in a sense, than the century she was singing in.

That is the thing that made me want the book. My subjects have mostly been dead a long time. My beat is the midcentury — the clubs and the live studios and the postwar stages, the world that built British and American popular music in the decades before anyone thought to call a singer a celebrity. Amy Winehouse belonged, by the calendar, to none of it. She belonged to the tabloid and the long lens and the camera-phone, to a machinery of exposure that would have been unrecognisable to the people I usually write about. And yet the oldest thing about her was the voice. She was carrying a cargo she had been handed across a North London kitchen table — Sarah Vaughan, Dinah Washington, Donny Hathaway, the whole Black-American jazz lineage refracted through a Jewish family in which the records had been the ambient condition of the household since before she could walk. My own beat was singing back to me out of a body fifty years too young to be holding it.

I wanted to know how that was possible. That is the only honest reason to spend three years inside another person's life.

The three years were not what I expected. I had assumed I would be writing about the ending — the addiction, the morality play, the death at twenty-seven that the culture had already filed and closed. And I was, in part, because those things happened and they are part of the record. But I kept finding myself somewhere earlier, and quieter: in a grandmother's flat full of Dinah Washington LPs, in the notebooks a small girl kept top secret until the poem inside them was finished, in the discipline that sat underneath the wreckage and that nobody who only read the papers ever knew was there. I worked from what could be verified — the public record, the inquest, the memoirs the people around her have published, the press that followed her from the first small mention in a trade paper to the last. I did not go looking for the woman the tabloids had sold. I went looking for the one who had done the work.

What I found was not a cautionary tale, because cautionary tales need the subject to be a warning, and Amy was never that simple. What I found was a craftsman: a songwriter whose instrument happened to be one of the great voices of the century, who wrote her own ruin down in real time and set it to a phrasing she had spent a decade of solitary listening learning to reproduce. The death is the fact everyone knows. The work is the fact worth a book.

This is my attempt to follow the voice from the Southgate kitchen where it was first heard to the Camden square where it fell silent — to hear it, if I can, as work rather than as tragedy. I came to it a partisan of an older music, expecting to explain a phenomenon and go home. I leave it a witness to a real one.

— Donovan Hadley, Manchester

Chapter 1 · The Jazz Singer's Granddaughter

There's a photograph from 1990 that survives in the family collection. A girl of seven stands on a kitchen chair in a terraced house in Southgate, North London. She is wearing a cardigan over a T-shirt. Her hair is dark and curly and has not yet learned to stay where she has put it. Her mouth is open. She is singing.

The adults around her are mid-meal. There are bowls of chicken soup on the table, a plate of salt beef, the chaos of a Jewish family dinner at which nobody has agreed about anything since approximately 1962. Her father Mitch, a cab driver with a decent tenor and a Sinatra obsession, is watching her with a kind of astonished love. Her mother Janis, the pharmacist, is watching with more reserve. Janis has always been the quiet one, the one who watches. Her older brother Alex, eleven, is rolling his eyes at the attention his sister is once again extracting from the room. And her grandmother Cynthia, who once dated Ronnie Scott before Ronnie Scott was Ronnie Scott, is watching with the recognition of someone who has seen this before, not this child, but this thing. The thing where a voice comes out of a body too small to contain it.

The song is a Dinah Washington number. The girl is seven. She is phrasing the line the way Dinah phrased it, behind the beat, sliding up to the note from underneath, holding the vowel a half-second longer than the melody demands. She has no technical vocabulary for what she is doing. She is doing it anyway.

When she finishes, the family applauds. Cynthia leans back in her chair and says, to no one in particular but to everyone in the room: "She got that from me."

She is probably right.

Amy Jade Winehouse was born at Chase Farm Hospital in Enfield on September 14, 1983, a Wednesday afternoon, four days past her due date. Her brother Alex had been born nearly four years earlier, in 1979. Mitch and Janis had been expecting a boy; Alex had been expecting a baby brother. When Amy arrived instead, she was named in the Jewish tradition that required an initial matching a departed relative's name: "A" for Mitch's late father Alec, just as Alex had been named. Her middle name, Jade, honoured the memory of Mitch's stepfather Larry's father, Jack. The family lived, at the time of her birth, in a small house in Southgate, one of the genteel Jewish-heavy North London neighbourhoods where the post-war Ashkenazi diaspora had settled after leaving the East End, the kind of suburb where the synagogues were reform, the accents were clipped but not pretending to be anything they weren't, and the expectation was that the children would marry other Jewish children and do slightly better financially than their parents.

Janis's family had immediately given Amy the Yiddish nickname "Nooge," the Yiddish term for a small person always pushing her boundaries, always testing the edges of the permitted. It was apt. Amy, in the subsequent accounts of the adults who watched her across her first four years, was accident-prone in ways that produced parental anxiety at a steady rate. She vanished in Broomfield Park when she was very small, requiring a police search of several hours before it emerged she had gone home with a friend of Juliette's mother, who had mistakenly assumed Janis had left. She hid behind the long coats in the John Lewis department store at Brent Cross shopping centre, discovered only after staff had been alerted. At Selfridges on Oxford Street she performed what Mitch subsequently described as the "choking game," throwing herself on the floor and coughing dramatically, before getting up and announcing she was fine. She had learned, very early, that the most reliable way to produce adult attention was to generate alarm.

The Winehouses had done about as well as the expectation required. Mitch drove a black cab (a London hackney carriage), which in the 1980s was still a respectable trade, with the Knowledge requiring three years of scooter-based memorisation of the city's streets and the licence commanding the kind of income that could just about sustain a four-person household in North London. Janis worked as a pharmacist. They lived in the house on Osidge Lane. They paid the mortgage. They shouted at each other about small things. They loved their children. Amy would later describe her childhood as happy, then as unhappy, then as happy again, in ways that tracked less with the objective conditions of the household than with whatever she had been drinking that week.

The marriage ended when Amy was nine. Mitch had been having an affair for most of the marriage with a secretary named Jane, and in 1992, he finally moved out to live with her. The divorce was amicable by the standards of divorces but was, for a nine-year-old who adored her father, not amicable at all. Mitch continued to visit. Mitch continued to sing Sinatra in the front room. But something had broken, and Amy, who was already, at nine, the kind of child whose emotional temperature registered things faster than the adults around her did, absorbed the break into the architecture of whatever she was becoming.

She became, across the subsequent years, a difficult child and a magnificent one, in approximately equal measure. She talked back. She questioned instructions. She drew on walls. She cut her own hair. She wrote in diaries that nobody was allowed to read and that, when they were read, turned out to contain the coded grievances of a pre-adolescent girl whose world had tilted. She was also funny, helplessly, continuously funny, in the North London vernacular that combined Yiddish lexicon, cockney rhythm, and an inherited Jewish grandmother's capacity for delivering devastating observations in exactly the register that made them impossible to refute. She was small. She had a big mouth. The mouth was connected to a brain that, from an early age, had the refusal to accept pieties that most brains, under social pressure, slowly lose.

And she could sing.

Everyone who knew her in childhood agrees about this. She could sing the way other children could run: naturally, without instruction, from some reservoir that the people around her recognised but could not locate. She was not trained. She did not learn to sight-read until later. What she had was ears. She could hear a vocal on a record and reproduce it in her own voice three bars later, with the phrasing intact, with the timing intact, with the particular breath the original singer had taken. Cynthia (Nan, in the family) had given her the records. The Dinah Washington albums. The Sarah Vaughan. The Ella Fitzgerald-Louis Armstrong duet recordings. Amy absorbed them the way other children absorbed Disney soundtracks. By the time she was ten, she had what the jazz musicians who would later meet her would call the ear: the ear for the space in a song, the ear for where the note wanted to land rather than where the metronome said it should.

The records came from Cynthia. The voice came from God, possibly, or from genetic accident, but the material on which the voice worked came from the Washington-Vaughan-Holiday catalog that Cynthia had placed in the family's listening habits across decades of aunts-and-uncles visits and Shabbat gatherings.

Cynthia Winehouse was, in her own way, the family's cultural spine. She had been, in her youth, a hairdresser at the Salon Raymond in Bond Street. She had dated the jazz saxophonist Ronnie Scott in the early 1940s, before Scott had opened the club on Frith Street that would eventually carry his name — had dated him through the wartime years when Scott was playing at London venues and working to establish himself in the London jazz scene. The romantic history went further. At a 1944 gig, Ronnie had introduced Cynthia to Glenn Miller, the American bandleader who was then on tour with his U.S. Army Air Forces Orchestra and who, according to Mitch's retelling of the story, attempted to steal Cynthia away from Ronnie. Scott proposed marriage. Cynthia said no. He later wrote about her in his autobiography. Amy, who absorbed these stories across childhood visits to Cynthia's flat, became obsessed with the detail: the idea that her grandmother had turned down the man who opened the most famous jazz club in London, and that there was, running through her grandmother's life, a direct wire to the 1940s jazz world that everyone Amy revered had inhabited.

The relationship had not lasted. Cynthia had married someone else: Alec Winehouse, Mitch's father, the paternal grandfather Amy's own initial would later be drawn from, who had died before Amy was old enough to know him. But the Ronnie Scott association remained in the family lore as a kind of credential. Cynthia had known jazz. Cynthia had dated jazz. Cynthia had, in her mythology, been part of the world into which her granddaughter would, decades later, walk. Mitch's uncle Leon was a professional horn player. Jazz was not, in the Winehouse family, an external cultural enthusiasm. It was the furniture of the household.

Amy absorbed it the way children absorb whatever saturates them. "I thought everyone could sing," she would say in an interview decades later, "until I heard my mum." The joke was at Janis's expense (Janis was, by any fair account, not a singer), but its architecture was the architecture of recognition: that singing was Amy's default mode of engaging with the world, as natural as conversation, because Mitch and Cynthia had made music the ambient condition of the household.

Cynthia died in 2006. She did not live to see Back to Black. She had, however, lived long enough to see Amy record Frank, and she had lived long enough to see her granddaughter sign to Island Records, and she had lived long enough to hear Amy, on the phone from studios in Miami and London, describe the shape of the career she was building. Amy got a tattoo of her grandmother's portrait on her right forearm in 2007, after Cynthia's death, as a ongoing act of remembrance. The tattoo stayed visible, in every photograph taken of her from that point forward, until the photographs stopped being taken.

The first performances were at home.

Amy sang, from the age of approximately four, for any adult who would listen. She sang on kitchen tables. She sang in the back seats of cabs when Mitch drove her to school. She attended Yavneh School nursery, attached to Southgate Synagogue, where she was apparently never difficult to locate — she could be heard from across the building, singing at the top of her lungs. At Osidge Primary School, which she attended on Chase Side in Southgate, she met on the first day a girl named Juliette Ashby, whose father, Jonathan Ashby, had founded WENN, the World Entertainment News Network. Amy and Juliette would remain close friends until Amy's death more than two decades later.

The music teacher at Osidge, who would later describe Amy's early vocal ability in terms that suggested something unusual had appeared in the school, encouraged her to audition for the school choir. Amy sang "Fly Me to the Moon" in the manner of Sinatra, which is to say, not as a seven-year-old should, but as an adult jazz singer with forty years of club work behind her. She was offered the lead solo for every concert for the next three years. She accepted with the confidence of a child who had never been told that singing at that level was remarkable, because in the Winehouse household it had never been treated as remarkable. It was simply what you did when you were happy.

The school concerts at Southgate were not, in the scheme of things, significant events. They were attended by parents, grandparents, and the occasional school inspector, in the multi-purpose hall, under fluorescent lights, with lyrics projected on an overhead. What was significant was the consistency of the reaction. Every adult who heard Amy at seven, at eight, at nine, at ten, reported the same thing afterwards. They said: that voice is not normal. They said: there's something wrong, or something right, with that girl. They said: she shouldn't sound like that yet.

By age nine, Amy had already committed the first small act of deliberate self-harm she would acknowledge publicly. She told Q magazine in 2007, in the candid interview whose honesty surprised even the magazine, that at nine she had tested the sensation out of a particular kind of morbid curiosity: "What does that feel like? Ow, that fucking hurts." She mentioned it without contextualizing it in therapeutic terms and without apparent distress, as a fact about herself she found interesting rather than shameful. The same year, nine years old, she heard her brother Alex playing Thelonious Monk's "'Round Midnight" through the wall of their shared-landing bedrooms on Osidge Lane. It was the moment she would later credit as her actual entry point into jazz: not her father's Sinatra records, not Cynthia's Dinah Washington LPs, but that piece of Monk floating through the plaster, with its blues-inflected suspended harmonies and its deliberate avoidance of resolution. She went to find the record. She found, alongside it, a stack of Alex's vinyl that included Ella Fitzgerald and Sarah Vaughan. The stack became her curriculum.

The thing they were describing was the quality that the adults in her family had already registered. The voice was not a child's voice. It was a contralto with cigarette-smoke notes in it, a voice that already knew things, a voice that had been, in the poet's formulation, more lived-in than the body that produced it. People who describe prodigies often resort to the vocabulary of the occult, because the vocabulary of development fails: Amy was not just precocious. She was, at seven, already doing vocal work that trained jazz singers in their forties worked their whole lives to do. The phrasing, the placement, the capacity to sit behind the beat without losing it, the capacity to modulate tone across a single sustained note: these were present from the beginning. They were not learned. They were given.

The question of where they were given from is unanswerable and useless. The question of what to do with them was the one that shaped the next twenty years of her life.

By nine, she had formed a rap duo with Juliette. They called themselves Sweet 'n' Sour. Juliette was sweet. Amy was sour. They were, in Amy's own later framing, "the little white Jewish Salt'n'Pepa." They wrote their own rhymes and rehearsed in the garage that Janis had converted into a bedroom, and performed them at school assemblies. Their material included a song called "Boys, Who Needs Them?" in which two recruited boys would appear onstage to list girls' names while Amy and Juliette dissed them. The Sweet 'n' Sour material was not, by the standards of nine-year-old performance, careful or restrained. Amy was already, at nine, writing in the register of a narrator who found boys largely inadequate and said so without apology.

At Osidge she played Rizzo in the school production of Grease in her final year, a choice that resonated: Rizzo, the sexually knowing, emotionally defended, witheringly funny girl who refuses to be contained by the conventions the musical's universe imposes. The alignment was precise. Amy's mother Janis watched the performance from the audience and recognised something she had been watching in the kitchen for years: the characteristic stance, head slightly tilted, the refusal to perform sweetness when the material required something more complicated. Amy did not play characters. She played versions of herself.

She was also keeping notebooks. The notebooks had, from an early age, been her primary creative space. She listed everything: what she wanted for her room, what schools her classmates were going to, the French words she would need on an upcoming Paris trip. She drew mind maps. She wrote poems. She wrote haiku (the Japanese three-line form, five syllables, seven syllables, five syllables) with the obsessive syllable-counting that would later characterise her approach to lyric writing. The work inside the notebooks was, by her own later description, top secret. Nobody was shown it until it was ready. When it was ready, when the poem or song had been revised down to the version she was satisfied with, she would sometimes present it, without preamble, to Janis or to Mitch. Then it was done. Then she moved on.

Juliette remained her best friend until the end. They had a complementary chemistry, Juliette the straight woman, Amy the unstoppable comic, that survived across fame, drugs, divorce, all of it. Juliette was in the Priory in 2011 when Amy was trying, once again, to stop drinking. Juliette was at the funeral. Juliette is, in the record of Amy's life, the witness who knew her before the voice became the career and who knew her after the career had become the prison.

The rap duo dissolved when Amy was twelve and discovered, via a BRIT School open-day brochure that Mitch had brought home, that there existed in South London a state-funded performing-arts school whose alumni included working pop musicians. Amy announced that she would be going there. Mitch pointed out that the school's catchment area did not include Southgate. Amy pointed out that the school's audition-based admissions did not care about catchment areas. The BRIT School, however, turned out to accept students only from age fourteen. For the intervening two years, Amy needed somewhere else.

The somewhere else was Sylvia Young.

Sylvia Young Theatre School sat on a row of Georgian houses on Rossmore Road in Marylebone, and it had produced, by the mid-1990s, approximately half of the under-eighteen talent visible on British television. Denise Van Outen had gone there. Emma Bunton had gone there. Nicholas Hoult would go there. The school charged fees that the Winehouses could not quite afford but that they found a way to pay, because Mitch had decided — over Janis's objection that Amy needed ordinary discipline rather than stage-school indulgence — that his daughter's gifts required nurturing.

Amy auditioned at twelve. She sang. She also read a monologue, did a cold reading, and answered Sylvia Young's questions about why she wanted to attend. Sylvia Young, a woman in her fifties who had been running the school since 1981 and who had seen thousands of talented children come through her doors, later described the Amy audition as one of the five or six she most vividly remembered. She said the voice was unlike anything she had heard from a child that age. She said the personality was even more striking than the voice. She said that Amy at twelve was already the Amy who would, five years later, be recording Frank.

Amy was accepted. She started at Sylvia Young at the beginning of the 1996 academic year.

The school was not built for her. It was built for the category of child who wants to become a mainstream working performer — a Denise Van Outen, an Emma Bunton, a competent dancer-singer-actor who can slot into West End productions, televisual variety, and the occasional film role. Amy was not that kind of child. She was, even at twelve, a jazz singer in training, a category that the school was not set up to develop and that the school, per Sylvia Young's subsequent interviews, did not quite know what to do with. Amy took the classes. She did the ballet. She did the tap. She did the acting. She did the musical-theatre ensemble numbers, which she hated, because she thought the bland chirpiness of the musical-theatre tradition was a betrayal of everything that the jazz records in her grandmother's collection had taught her about how singing was supposed to feel.

She was, by the standards of the school, a difficult student. She talked in class. She questioned her teachers. She wore nose studs in violation of the uniform code. She cut her own hair into a bob that the school asked her to grow out. She fought with classmates. She made the other Jewish girls laugh inappropriately during Friday assembly. She was warned, suspended, re-warned, re-suspended. Sylvia Young herself, in her subsequent public reflections on Amy, held the two facts in the same sentence: the extraordinary talent — "almost a genius," she would say of Amy's writing — and the naughtiness. Amy's deficiency at Sylvia Young was not talent. It was compliance. She had too much of the former and not enough of the latter for the institution to absorb.

Some of her Sylvia Young classmates became significant figures in the same cultural moment that Amy herself would inhabit. Tyler James, the Tyler who would be her closest male friend until her death, who had first handed Nick Shymansky the cassette tape that produced Amy's management deal, was a Sylvia Young contemporary. Billie Piper, then an aspiring pop singer who had not yet had her first hit, was in the school at the same period. Matt Willis, later of Busted, was among the students. The school was, in the way that performing-arts schools produce cultural clusters, a training ground for a particular generation of British entertainment culture. Amy's relationship to the cluster was characteristically ambivalent: she knew Tyler, loved Tyler, would carry the Tyler friendship for the rest of her life; her relationship to the pop-star-manufacturing apparatus the school existed to supply was pure skepticism. She was not there to be manufactured. She was there to learn to sing, which she had, by the assessment of everyone who heard her, already been doing better than anyone in the school when she arrived.

The school had provided, in its extracurricular activity list, an entry point into professional performance that Amy exploited with more determination than her classroom behavior suggested she was capable of mustering. She appeared in a small television production as a child actor (playing a character named Peasblossom) and in a stage production of Don Quixote at the London Coliseum, for which she was paid eleven pounds per performance. She auditioned at a talent competition in Cyprus, where her singing of "Sunny Side of the Street" was noted by a reporter from The Stage, the British entertainment trade paper. The Stage mention, small, brief, in the industry paper that the professionals read, was her first professional press mention. She was thirteen.

In the end, she left the school. The terms of the departure have been blurred in the retellings, but the two adults closest to the decision told the same story: Sylvia Young repeatedly made it clear that Amy was not expelled, and Mitch likewise denied the expulsion reports — the family had moved her. Amy, in her own later accounts, sometimes claimed the expulsion anyway, depending on the rhetorical purpose of the story. What is not disputed is that she left Sylvia Young at the end of 1997, at age fourteen, and that she spent the subsequent months at Ashmole School in Southgate, the comprehensive where Alex had gone, before re-auditioning for the BRIT School and being accepted for September 1998.

The Sylvia Young years left, on the adolescent Amy, a residue that the rest of her life would draw on. She had learned, at twelve and thirteen, that she did not respond to institutional structure. She had learned that she could extract admiration from adults without giving them the compliance they expected in return. She had learned, most crucially, that her voice was the one asset that none of her other difficulties could diminish: that no amount of rule-breaking, no amount of uniform violation, no amount of talking back to teachers, could cause the music staff to stop asking her to sing at school events. The voice was the thing that made her unfireable, even from a school that was, by the end of her second year, actively trying to fire her.

She absorbed the lesson. She would carry it forward, into every subsequent institutional relationship, for the rest of her life.

By fourteen, she had a guitar. It was an acoustic, bought by Mitch at a Denmark Street shop for approximately a hundred and fifty pounds. She taught herself to play. She used chord books at first, then started working out songs by ear from records. She learned the walking bass lines that underpinned the 1960s soul records she was beginning to discover through her Dad's old CDs. She learned the comping rhythms of jazz guitar. She was a competent but not spectacular player (her hands were small, her technique was unrefined), but what she could do on a guitar was exactly what she needed to do to support her own vocal compositions, which was a combination of rhythm and harmonic structure that would free her voice to do whatever it wanted to do on top.

She began writing songs at fourteen. The first ones were bad. The second ones were less bad. By fifteen, she was writing songs that were no longer obviously student songs, songs whose harmonic progressions, whose lyrical choices, whose rhythmic construction, were all operating at a level that her brother Alex, watching her at a family barbecue in 1999, described later as "frightening."

The combination of what she could do (the voice, the ear, the harmonic instincts, the rhyming craft, the black-comic sensibility about male-female relationships that she had been developing since the Sweet 'n' Sour era) was already, at fifteen, the combination that would, four years later, produce Frank and, seven years after that, produce Back to Black. She did not yet know this. Nobody around her knew this. What the people around her knew was that the kid from Southgate was writing songs that were better than she should have been capable of writing, and that she was singing them in a voice that should not have been coming out of a fifteen-year-old's body.

The BRIT School received her in September 1998. She lasted, per various accounts, between twelve and eighteen months. The precise duration is disputed. What is agreed is that she left before completing the program, that she was bored, that she was already performing in small London jazz venues with her guitar, and that the school, like Sylvia Young before it, was not set up to accelerate a student who was already operating, in artistic terms, beyond what the curriculum could teach her.

She was sixteen. She was singing jazz standards in pubs in Islington. She was writing original songs that nobody had yet heard outside her bedroom. She was being noticed by the early-2000s London music-industry people whose job it was to notice things, and she was, across the 2000 and early 2001 period, being steered toward a meeting that would change the direction of the life that had been, until then, organised around the North London geography of school, synagogue, and the cab ranks where her father worked.

The meeting would produce a management deal. The management deal would produce a record deal. The record deal would produce Frank, which would produce the reputation. The reputation would, eventually, produce everything else.

Chapter 2 renders the meeting.

Chapter 2 also renders Sylvia Young more fully (not as the institution that failed to contain her but as the institution that first attempted to) and renders the early years of the London jazz-pub circuit on which she was, at sixteen, already an emerging presence.

She was a jazz singer's granddaughter. She was a pharmacist's daughter. She was a cab driver's daughter. She was a North London Jewish girl from Southgate whose bedroom wall featured posters of Sarah Vaughan and the Shangri-Las in approximately equal proportion.

She was, at fifteen, already herself.

The rest of the story is what the world did to the self.