Winona Ryder
Raised in the Colombian compound of Chilean revolutionists and then on a commune in Northern California, Winona Ryder was sent to cure her loner ways at San Francisco's American Conservatory Theatre in 1982. While studying there, she caught a talent scout's eye and started auditioning. She made her feature debut in "Lucas" before becoming the poster girl for Gen X and goth kids with iconic roles in "Beetlejuice," "Heathers," "Edward Scissorhands" (where she met future fiancé Johnny Depp) and "Reality Bites." She won her first Golden Globe and got her first Academy Award nomination for 1992's "Age of Innocence." A Best Actress nod for "Little Women" came in 1994. Just after breaking up with Matt Damon and starring in "Girl, Interrupted," she was caught shoplifting $4,760 worth of merchandise at Saks Fifth Avenue in 2001. The ensuing trial exposed her psychological instability and painkiller abuse. She had previously sought treatment at a psychiatric hospital in 1990 after dropping out of the third "Godfather" film. It also sparked the "Free Winona" T-shirt craze. After retreating from the spotlight for a half decade, she triumphantly returned as the real-life girlfriend of Rilo Kiley guitarist Blake Sennett, Spock's mom in the first "Star Trek" reboot and a cracked prima ballerina in "Black Swan."