Winona Ryder — in 1988 and 2012
Doe-eyed actress Winona Ryder stole hearts in '80s films like Lucas, Beetlejuice, and Heathers, and went on to become synonymous with Gen-X slacker chic. After a much-publicized shoplifting conviction in 2001, the now 40-year-old has made her way back to the spotlight with cameos in big films like Star Trek and Black Swan. No matter what, we'll always have a cherry slushee in our hearts for her. Any woman who can inspire Johnny Depp to get her name tattooed on his bicep goes down as legendary in our books, arewerite?