Anna Nicole
Smith

She's not our $450 million Playmate anymore, but Anna Nicole is still in the money. After years of court battles over her late husband's billions, a federal judge has awarded Anna a respectable $88.6 million from his estate. We've known she was worth her weight in gold since 1993, when we crowned her Playmate of the Year. Take another look at the exquisite photographs from Anna's heyday that appeared in Playboy's February 2001 issue.