40. Kate Moss
Sure, Kate's heyday was in the '90s, but in our era she settled into an appealingly sleazy lifestyle while dating British junkie rock star Pete Doherty. And then look what Katy did next: proving all those Say No to Drugs campaigns wrong, she actually made more dough after flicks of her doing blow were published. She nose what she's doing!
DECADE ACHIEVEMENT: Making her Supreme photoshoot one of the most ubiquitous images out there today.