23. Paris Hilton
Occupation: Reality TV Star
Hilton's been a wayward girl long before One Night in Paris. When she was 16, she spent a year at a school for emotionally troubled teens. At 18, she was kicked out of her high school. And at 19, she was considered "New York's leading It Girl" and was absorbed into the L.A. party scene. 2006 started Hilton's streak of car troubles (namely a DUI and a suspended license) and, in 2007, she also spent some time in jail. Most recently, in 2010, Hilton was suspected of smoking marijuana at a FIFA game, and was arrested on suspicion of cocaine possession in Las Vegas.