The Beetlejuice beauty, Winona Ryder stepped into the scene as a teen starlet that had everybody gushing over her. She won over the hearts of the nation and actors on and off the screen. She had flings with A-listers such as Johnny Depp and Matt Damon. Winona played major roles in major films like Heathers and Edward Scissorhands before her 2001 run-in with the law after stealing from Saks Fifth Avenue. The starlet laid low for the next few years but made a major comeback with her appearances in Star Trek and Black Swan.