On her best days, Amy Winehouse is a mess. The 24-year-old wears her hair in a beehive so large and teetering that it could hide the chorus of middle-aged black women that seems to materialize at the back of her throat whenever she sings. Having once thought herself overweight, Winehouse now keeps her body little-girl tiny and covered with enough tattoos to earn her cred at a medium-security prison. Onstage, she's known to favor poodle skirts. It's an aesthetic that takes some getting used to.
On her worst days—and there have been plenty of late—Winehouse looks a safe bet for an early grave. After a 2007 full of well-chronicled erratic behavior ranging from mumbled concert performances to a drug arrest in Norway, her in-laws pleaded for a public boycott of her music so that she and her equally troubled husband, Blake Fielder-Civil—currently in jail for attempting to bribe a bartender he allegedly assaulted to drop the charges—might be deprived of the income they spend getting wasted. One day in December, Winehouse wobbled out of her London home at 6 a.m. wearing only jeans, a red bra and a look of complete befuddlement. On Tuesday video of her (now blond) snorting and smoking various substances hit the Internet.
Nothing inspires scorn like wasted fame—or kills nuance like a fire-engine-red bra. But to dismiss Winehouse as just another train wreck is to presume that she has no idea she's off the rails, and this distinction matters when considering how to feel about her. Winehouse's Back to Black is up for six Grammy Awards on Feb. 10, including one for Album of the Year. While the Grammys are notorious for their grandfatherly taste (she'll be competing against Herbie Hancock, among others), they're spot-on about Winehouse. On Back to Black she sounds like Dusty Springfield teleported into the hip-hop era. The songs—all of which move with the economy of old 45s and all of which Winehouse had a hand in writing—tell tight, complicated stories, but more important, they tell her stories.
From the first line of the album—"They tried to make me go to rehab/I said 'No, no, no'"—Winehouse is in complete control of her out-of-control tale. "You know that I'm no good," she sings with remarkable power and sinew in another song, and it's not a boast, though her put-downs of the men who would take advantage of her certainly are. Throughout, she's mouthy, funny, sultry and quite possibly crazy, yet unlike Britney Spears or a dozen other pop idiot savants, Winehouse not only knows who she is but is able to express it in a way that's often beautiful and meaningful to others. Traditionally, we call that art.
The last time pop music was dealt this card, it went by the name Kurt Cobain, another lower-middle-class kid for whom being messed up was a source of creativity and, eventually, the killer of it too. Cobain told his few high school friends that he had "suicide genes," and there's a dangerous echo of that infatuation with doom in Winehouse's fetish for ill-fated soul singers. No matter how true her music feels, it's hard to tell the difference between pain and performance and impossible to guess how approval reinforces her self-perception.
Still, boycotts and scorn are the wrong response. For one thing, they're not likely to work. For another, we're supposed to encourage people who feel doomed to share it in words and know that others can relate. The law can take care of their actions, and in Winehouse's case, it already has: she's likely to miss her Grammy moment because of the visa issues that go along with being a danger to yourself. But that doesn't mean you shouldn't root for her.