Amy Winehouse, the British singer who died last weekend, was a paradoxical artist. Did she, could she, really understand what she was doing? Her social behavior, convulsed by myriad addictions, was atrocious—a spectacle of assaults, drug arrests, and public embarrassments as she emerged from one spot of trouble and dove into another almost reflexively. She was boozy and disheveled, a tarted-up gamin somehow reminiscent both of a blowzed '60s pinup and a canny street urchin, all wrapped up with the bow of her almost Dickensian name on top. Yet she radiated precision and formalism in her music. Her gaze on a stage could be vacant, almost affectless. But somehow her albums betray an astringent intelligence, over- and undertones of meaning and calculation, and a surprisingly nuanced grasp of the music she loved from decades long past. And her arresting voice conveyed not just emotion, but on occasion universal cataclysms of love, loss, and degradation.
The obits talked too little about how her art worked. The marriage of her artistic sensibilities was as unusual as her appearance. She purveyed a relatively soft sound, neo-jazz on some tracks, retro soul on others, shot through with the heart-bursting emotionalism of the girl groups of the 1960s, yet all brought down to earth with the petulance, grittiness, and self-indulgence of hip-hop. She didn't rap per se, but the sensibility of this rough milieu, reinterpreted through her unfailingly feminine sensibility, informs all of her music.
Her first album, Frank, introduced us to her musical and lyrical concerns; her second, Back to Black, with the assistance of knowing DJ/producer Mark Ronson, matched her with a crack backing ensemble whose sound—modern and retro all at once—made her an international sensation. Her voice was an instrument capable of doing business with the antecedents she revered, which is saying something. And her lyrics almost always repay a close listen, leaving the hearer to unpack the music and the words. A casual reference to a lover named Mr. Jones takes you back to '70s soul ("Me and Mrs. Jones"), and then '60s rock (Dylan's "Ballad of a Thin Man"); infidelity and cluelessness are thus encoded into the song. In time you realize this particular Mr. Jones might be heroin, too—another subject that has coursed back and forth through decades of pop, soul, and jazz. Such tropes occur in her music far too much to be accidental.
Indeed, Winehouse's intents are plain. Other songs, less deliberately allusive, go down rabbit holes of romantic and sexual rationalization, but often with an element of what might be called mischievousness were the subjects not so unsavory. In one cold-blooded track on her first album, the grandiosely titled "I Heard Love Is Blind," Winehouse insists to her lover that a dalliance she'd had didn't mean anything. But as the song goes on, she twists the knife ("I couldn't resist him/His eyes were like yours"), progressively dropping ever more explicit details of the encounter—the ones she could remember, anyway: "It was dark and I was lying down."
Yet somehow, when married to the spare guitar and the unerringly tasteful jazz-flecked accompaniment her producers conjured up for her, the song is persuasive. Her work was serious and mocking about characters deluded and self-knowing—about infidelities, perversions, drug use, and toxic emotional extremes. She knew they were toxic, but they were hers nonetheless, and the songs she wrote were defiantly frank epistles from the underground she inhabited.
Winehouse, you see, had a plan: She used that twisted sensibility to reclaim certain jazz and pop idioms for a new generation, building on the formidable female figures that distinguished '50s and '60s classic sounds—from Billie Holiday, with whom she shared a deceptively dulcet voice, to Sarah Vaughan to the beehived presences of the girl group era. Without having to articulate the fact, she made it clear she implicitly understood the real lives behind those public personas—lives that in many cases, truth be told, involved grimy tales not all that different from her own.
The title song of her second album, Back to Black, begins with a clanking piano that effortlessly summons up the jaunty heyday of the Motown years, and you wait expectantly. . . to hear Diana Ross sing. But then you notice an odd minor note in the jauntiness, and then an unprintable phrase in the second line. And suddenly you're deep inside a junkie lament, yet captivated by the self-knowledge on display. When Winehouse sings, "I died a hundred times," she doesn't specify whether she's singing about drugs or love at that particular moment. In Winehouse's world, junkies loved, too.
There are stars whose death seems to cap a career, and those other more promising ones who passing creates a sense of lost potential. The fact that her second album, now five years old, trumped the promise of the first would seem to put Winehouse in the latter category, and that is a shame. One doesn't like to judge, but I'm going to go out on a limb and say that that five years of lost creativity, not to mention being a cadaver before one's 28th birthday, represents some poor life decisions. Where did Winehouse go wrong?
She grew up working class with a cab-driver father who'd dreamed of being a singer, too. Her early love of jazz and soul, seemingly inculcated from a young age, exuded from every track she recorded. In a transfixing film of an early audition she made at a record label, she is a unexpectedly demure presence, warbling winningly as she perches on a piece of generic modernist office furniture.
The road to the emaciated mess wandering down a London street shot by paparazzi just a few years later is unclear. While her initial performances were by all accounts sensations, by the time she was being filmed by a proper camera you can see the toll her lifestyle had taken on her art. Her presence was eerie: a beehive towers over a face heavily made up into almost a cubist set of planes. Her tattooed arms poke out of incongruous babydoll dresses. And there's that glassiness in her eyes, a bit of the automatic in her articulations. Some, perhaps all, of this persona may have been deliberate; perhaps she was showing the audience a simulacrum of the artist as disappearing addict. If so, it was convincing. In any case we can only mourn the child who was born with prodigious gifts but not the personality to use them to create a life worth living for herself.
Back on her first album she larked her way through a track called "October Song." The lilt in her voice was never more reminiscent of Holiday as she sang:
Ava was the morning/ Now she's gone
She's reborn like Sarah Vaughan
At its silkiest, Winehouse's voice was compared to Vaughan's, too. * As the track goes on, it's hard not to hear Winehouse, perhaps, singing to herself:
She spoke until one day she couldn't be heard
She just stopped singing.
But keep listening to "October Song" and you can hear more. "I sing a lullaby of birdland every night," she murmurs, and when the chorus comes along you can hear the melody from the George Shearing classic she's referring to bubbling up. Birdland the jazz club, which the "Lullaby" honored, was named after Charlie Parker, a junkie who, like Amy Winehouse, died too young. Winehouse's song, recorded before she was 20, is hard to listen to at a sad time like now. It reminds us how with just a few words and bits of melody she found in her songs, over and over again, beauty and despair, love and an all-too-portentous decline. She skipped, by turns merrily and bleakly, through the musical decades and the similarly fated lives that formed her.
Correction, July 26, 2011: This article originally misspelled Sarah Vaughan's surname. (Return to corrected sentence.)