38. Winona Ryder
In 2001, Winona Ryder was arrested for shoplifting over $5,500 worth of designer clothes from Saks Fifth Avenue, including using a fake prescription. She claimed it was research for a role but was convicted and sentenced to probation.
The high-profile theft shocked fans and halted her career temporarily. Paparazzi frenzy followed, but the personal struggles (including painkiller addiction) that may have contributed stayed private amid the tabloid circus.
