Most Infamous Moment: In December of 2001, Ryder was arrested on shoplifting charges in Beverly Hills, California. She was accused of stealing $5,500 worth of designer clothes and accessories at a Saks Fifth Avenue department store.

Winona’s one way ticket into the bad girl Hall Of Fame came when she was arrested for shoplifting, but more of her problems surfaced once she hit the court room. While on trial, she was accused of abusing drugs, including oxycodone, valium and vicodin, without prescriptions. Yep, this gorgeous millionaire decided to go all Ocean’s 11 on us. But, alas, George Clooney she is not. She was busted. Thriving career, interrupted.