Late last year, I spent the better part of a month working on a lengthy profile on Amy Winehouse, the British Jewish retro soul singer who tragically died over the weekend at 27. It was in the doldrums of this process, which included reading a book about Jewish immigrants who perform in blackface in the early 20th century and researching the bizarre music producer Phil Spector, one of her primary musical influences—that I was forced to ask myself: Why do I like Amy Winehouse so much?
I had become an instant fan of the singer almost from my first listen to “Back to Black” in 2007, Winehouse’s second and now final album. At first, like many others, I was very taken by the ballsy track “Rehab,” where she famously rejected the help she so clearly needed. Yet at the time of the track’s release, she hadn’t yet spiraled out of control. Her refusal seemed as much a denial of her alcohol and substance abuse problems as an aversion to the type of image rehab that many actors, singers and politicians are forced to undergo in order to make them more palatable to the general public.
Winehouse seemed immune to this kind of image meddling. As a Jewish woman raised in a strictly Orthodox community, I identified with her refusal to be controlled if not her choice of transgressive behavior. (My habit of wearing pants can hardly be considered self-destructive.)
It was this unrepentant behavior that signaled Winehouse’s place in a very different line of Jewish women—not the “nice” ones who make you chicken soup when you’re sick or assure their sons that they’re the smartest boys in the world and any woman would be lucky to marry them. Winehouse’s ancestors are the biblical vixens: Dina, who slept with Shechem; Deborah, the biblical heroine; or, more recently, Monica Lewinsky, the “portly pepperpot” (as The New York Post dubbed her) who nearly ended Bill Clinton’s presidency. These women possessed sexuality so powerful and intoxicating that it influenced national and political outcomes.
Her devil-may-care attitude extended to her live performances. Even at her best, Winehouse shimmied awkwardly and endearingly as she sang onstage. Her doo wop-styled back-up singers were far more at ease, nimbly dancing behind her. Winehouse herself was never quite ready for primetime, and yet she was embraced by the music industry and mainstream, recognized for her adenoidal voice and towering songwriting talent (and beehive) with the Mercury Prize and several Grammy Awards.
Yet Winehouse wasn’t always a “bad girl.” She once was a freshly scrubbed Jewish teen from northeast London. Back when she recorded her first album, “Frank,” at 19, she was curvier and wore her long dark hair in loose waves. There was nary a tattoo in sight. True, she had been kicked out of a prestigious stage school (the same one that Adele attended) for getting her nose pierced, but that’s hardly scaling the mountain of teenage rebellion.
This younger Winehouse had been nurtured both artistically and religiously by her family. Her parents and paternal grandmother, Cynthia, who once dated the legendary musician Ronnie Scott, raised her on a steady diet of jazz greats and soul singers from Billie Holiday to Ella Fitzgerald to Dinah Washington. It was also Cynthia who hosted weekly Friday night dinners. Her death in 2006 is said to have precipitated her granddaughter’s downward spiral.
It was at this time that Winehouse entered the studio to record “Back to Black.” She changed musical course on this album, veering away from the adult contemporary jazz sounds that had dominated “Frank” into darker lyrical terrain set, almost paradoxically, to the sunny sound of the ’60s American girl groups that had been helmed by Spector.
Under the poppy cloak of the Ronettes’ sound from 40 years ago, Winehouse brought a thoroughly modern—and Jewish—sensibility to her lyrics and performances. She spoke not of love and romance, as her predecessors did, but of addictions, sex and every Jewish girl’s favorite emotion, guilt. Her songs and tone dripped with regret, but also the inevitability of her bad behavior. Any astute listener knew that she probably wasn’t going to change.
Yet her fans held out hope, as did her family and probably even the troubled artist herself. Ultimately, however, like an Old Testament prophet, she foretold her own fate. On the titular track of her master work, she sang, “I tread a troubled track/My odds are stacked/I go back to black.”
(This article was adapted from a piece that first appeared in the online magazine Tablet.)