Where the 1990s saw the untimely passing of Gen-X icons like Kurt Cobain, Gen-Y celebs like Britney Spears and Lindsay Lohan spent the 2000s veering dangerously close to disaster without meeting it completely.
Until Winehouse. The pint-sized brunette with the beehive and soulful voice had been a tabloid-fixture for years, for her drug uses as much as her music. However, as Jezebel.com contributor Lane Moore put it, "For every one of her documented missteps, I never once thought, 'How is she still alive?" She was just 27.
Pick up the October issue of Cosmopolitan on sale now to find out why 27 is such a life-defining age. Plus, for other stars who've joined the infamous 27 Club, click here.
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