Anna Nicole Smith
Playboy's 1993 Playmate of the Year, Anna Nicole Smith made news for her curves and her twos, not necessarily in that order. Put it this way, if a woman was ever built to be a playground, ANS was it—at least in those early days. She modeled, changed her name (from Vickie Lynn Hogan to Vickie Smith to Anna Nicole Smith), replaced Claudia Schiff-heerrrr in the Guess campaign, and then married a billionaire 63 years older than her, but not for his money. It was for his stamp collection and the way he made hot chocolate before going to bed. She's dead now. RIP, ANS.