She has been in the film business for nearly two decades, rising up from an unconventional childhood on a California commune, to reach the status of an elite Hollywood actress and artist. Ryder has been nominated twice for the Oscar, and has taken the reins on such critically acclaimed films as Girl, Interrupted. However, her journey to success has not been an easy one. From her famed three-year relationship with actor Johnny Depp, to her notorious 2001 shoplifting scandal, Winona has maintained a certain haunting mystique surrounding her personal life. Fans might not always understand Winona Ryder. But that seems to keep them all the more interested.