A Hot Mess

But despite the obvious pride and care her father shows her and the affection she returns, Winehouse has not always been lyrically kind to him. On her first album, in “What Is It About Men,” she explains why: “Understand, once he was a family man/ So surely I would never, ever go through it firsthand/ Emulate all the shit my mother hated/ I can’t help but demonstrate my Freudian fate.” Instead, she seems to have been most controlled by—and therefore perhaps most influenced by—her grandmother, who hosted weekly Friday-night dinners at her London home for the family. In fact, it was Cynthia’s death in 2006 that has been blamed, at least in part, for Winehouse’s subsequent downward spiral. Winehouse had been a woman grounded by another woman, not by men.

Perhaps this offers a clue to why she changed course for her second album, moving from the adult contemporary jazz sounds of Frank to the sound of to the ’60s American girl groups. At first listen, it might seem highly incongruous to match Winehouse’s explicit lyrics with the melodies and harmonies of the Ronettes. On the track “Me and Mr. Jones (Fuckery),” (a reference to Nasir Jones, better known as the rapper Nas), she sings, “Nowadays you don’t mean dick to me.” In the background, the backup singers’ harmonies swell sweetly—“Dick to me,” they repeat after Winehouse. A few verses later, when she sings about Sammy Davis Jr., the backup is at it again, providing unintentional humor. “Best black Jew” rises up and lingers in the air as Winehouse continues.

The first song Phil Spector produced was “To Know Him Is To Love Him,” a ballad whose title was the epitaph on his father’s tombstone. Phil Spector earned his first No. 1 hit with this song, as part of the Teddy Bears. This would be the only time he performed one of his hits; after this point, he would be known only as a producer. The song, which was written as a son’s tribute to his father, becomes a slavishly romantic tune through lead singer Annette Kleinbard’s sweet, artless soprano. Spector backs her on the guitar and harmonizes with the third Bear, Marshall Lieb. This is exactly the kind of a song you’d expect from a man of Spector’s insecurities and neuroses, the kind of man who had been hounded by a domineering Jewish mother for most of his life. What would he want most of all? A woman absolutely devoted to him, one who would say things like, “Just to see that smile/ Makes my life worthwhile.”

It is safe to say that Winehouse could never be that woman, and in her hands the song, which she frequently performs in concert, sounds subtly but critically different. Instead of Kleinbard’s clear, high-pitched tone, Winehouse brings it down several octaves and adds a raspy tinge to her delivery, backed by a simple acoustic guitar. One gets the sense that as Winehouse sings, “Oh, I’ll be good to him/ I’ll bring joy to him,” she is aspiring to be her better self, the kind of woman who is devoted to her man without making demands (perhaps the Jewish mother who dotes on a husband and son, one that Spector wished he had and the type Winehouse wishes to be). This is not a song she could write on her own. Her father has conceded this point. “She’s never gonna write a song about, ‘You look lovely in the moonlight, my darling, give me a kiss,’ ” he told the Huffington Post in early 2010. “Every song Amy writes is like … [He sticks an imaginary knife into his substantial tum and circles around as though he is eviscerating his entrails.] In Yiddish, it’s ‘schlapping your kishkas [your insides] out.’ Amy’s a great one for schlapping her kishkas—because every song is, like, heartbreak … sorrow … depression.”

If Spector and Winehouse met in real life (say, perhaps, in prison), it is unlikely that they would find much physical and sexual attraction. Spector is the type of man that she would never end up with—slight, light, and sickly. (One-time band mate Kleinbard once recounted being on a double date in a car with Spector, whose heavy breathing coming from the back she imagined to be heavy petting—until Spector cried out: “I’ve got to get out of here. I’m having an asthma attack.”) In contrast, Winehouse is the one with overwhelming needs, which makes her incapable of meeting those of others. Her compositions tend to be about men who fail to measure up to her standards or, conversely, how she has wronged them. Winehouse does not put her lovers up on a pedestal and is unable to express the slavish devotion a true Spector song (and Spector himself) demands. Even as she sings him promises, it sounds like she already let him down.

This is precisely the type of man Winehouse sings about on her first album, Frank, which established her as an up and coming British singer (and for which she was nominated for the Mercury Prize, a prestigious award). On “Stronger Than Me” she explains her frustration with a weak man, the type who constantly needs to be bolstered: “You should be stronger than me/ You’ve been here seven years longer than me/ Don’t you know you’re supposed to be the man/ Not pale in comparison to who you think I am.” Her voice on this track is higher and more nasal than it is on “Back to Black,” sort of like the British answer to Fran Drescher. Imagine the nanny issuing this put down: “Feel like a lady/ And you my lady boy.” Accusing her guy of being so feminine that he could easily be mistaken for a transsexual takes shrewish, Jewish nagging to a whole new level.

And even when Winehouse tries on subservience it still comes off as awfully dominant. “I’m not gonna meet your mother anytime/ I just want to grip your body over mine,” she sings a few verses later. Though she describes vanilla, missionary-style sex, the very fact that she’s the one grabbing, placing her partner where she wants him negates her location. Even when she’s the bottom, she’s also the top.

This masculinity that she looks for in men but almost loathes in herself is manifest in her appearance—the bouffant hairstyle, the breasts (surgically enhanced) propped up to her collarbone, the Cleopatra-style eyeliner, the exceptionally tight vintage dresses. All of it represents an exaggerated form of femininity, which is the hallmark of drag. To dress up as Winehouse, a queen would not have to embellish at all. It would not be possible to make the hair any bigger or take the boobs any higher. Her look is prepackaged drag. If she accuses men of acting like women then she too is masquerading—a woman who dresses like a man who dresses like a woman.

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So, if Winehouse is too dominant and aggressive—too manly, even—for Jewish men, even most non-Jewish men, who can handle her?

In real life, she’s gone for skinny white junkies who fob off her fame and wealth, but in songs she has teamed up with a beefier sort: African-American rappers. Jay-Z remixed Winehouse’s monster hit, “Rebab,” while Ghostface Killah sampled the beats, horns, chorus, and some of the verses on a track of the same name and seems to be in a constant dialogue with her with his rhymes. As Winehouse sings about being “trouble,” he raps in response, “Fight scenes, I take the good with the bad.” But why is he willing to overlook her shortcomings? Because she lives up to the Jewish sex goddess stereotype: “Cuz you give the best brains I ever had.” Winehouse’s ex-husband, Blake Fielder-Civil, made a similar assertion though not in rhyming verse: “She is even better at sex than she is at singing,” he told a British tabloid. Winehouse’s sexuality is powerful. Yet even Ghostface seems a bit wobbly by the song’s end. On the outro, the rapper repeats the phrase “Got to forgive the past but I never forget it,” as though the memory of his humiliation at the hands of a superior feminine force will somehow keep the pleasurable but ultimately traumatic cycle of infatuation, narcissistic self-fulfillment, and sexual abandonment from repeating itself yet again.

Dvora Meyers is a freelance writer based in Brooklyn. She dressed up as Amy Winehouse for Purim.