Playboy’s 10 Sexiest Playmate Winners of All Time

9. Anna Nicole Smith – 1993 Playmate of the Year

Anna Nicole Smith (born Vickie Lynn Hogan) is just one of the classic faces of Playboy history, so of course she had to be named. Arguably known as probably the most famous Playboy bunny ever, this multimillionaire was Playboy’s 1993 Playmate of the Year.

It all started after a test shoot in 1992, when Hugh Hefner loved her look so much that he decided to make her the cover of the March 1992 issue. Overnight she turned into a modelling sensation and was even compared to the likes of Marilyn Monroe, Playboy’s first cover model.

She has since modeled for magazine such as Italian Vogue, Vanity Fair, Marie Claire and Harper’s Bazaar. That doesn’t stop her from being one of the biggest gold diggers in Hollywood history though!