Six months ago, when many of us heard Amy Winehouse’s “Rehab” for the first time, the song sounded like a gloriously defiant middle-finger salute to authority figures everywhere. In this case, the authority figures happened to be record-label execs, but, depending on your situation, you could easily substitute parents, teachers, employers, or repressive government leaders: anyone threatened by unabashed rebellion.

These days, the song is starting to feel sad, maybe even slightly pathetic. Winehouse has spent most of the summer missing gigs, ostensibly because of health concerns, although she has consistently found the strength to make it to the neighborhood pub and knock back a few rounds. Last week, she was briefly hospitalized due to what publicists labeled “exhaustion,” but Winehouse herself hinted was a life-threatening drug overdose.

At a time when the tabloid media is obsessed with every aspect of Britney Spears’s ongoing psychodrama (“Are those really morphine lollipops she’s sucking on?”), the fact that she once made (very bad) pop records is incidental to the voyeuristic obsession. But for real music fans, the derailment of Winehouse and one of her obvious role models, Lauryn Hill, is not a kitschy sport. It’s a demoralizing spectacle.

Hill, like Winehouse, had a rough week. Her August 6 free concert at Brooklyn’s Wingate Field sounded eerily like a recent show in Oakland: She arrived two hours late, could barely carry a tune for much of the show, babbled incomprehensibly, and looked like Oprah Winfrey in a clown suit. While it’s surely superficial to wonder what happened to the gorgeous Hill of 1998, it’s worth pointing out that on her 2002 MTV Unplugged album, she talked about the need to remain natural, to forsake show-biz artifice, and yet she now wears layers of randomly applied makeup, absurdly long false eyelashes and a roof-raising auburn fro.

You sense that she’s testing the waters for a comeback, but you also sense that she’s confused and conflicted about how to approach it. Both Wyclef Jean and Pras recently blamed Hill for thwarting a possible Fugees reunion album.

Like Hill, Winehouse is an uncommonly gifted, relentlessly honest artist fascinated by the connections between R&B, hip-hop, and reggae. She’s even covered Hill’s “Doo Wop (That Thing)” on occasion. While Hill is so complex and mysterious it’s hard to know what is driving her difficulties, she and Winehouse seem equally uncomfortable and embarrassed by their fame, and when you factor in Winehouse’s obvious attraction to the live-fast, die-young myth, the potential for disaster is immense.

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