47. Bijou Phillips
The daughter of John Phillips, of the Mamas and the Papas, moved into her own New York City apartment when she was only 14, after quitting school. During her early teen years, she'd frequent nightclubs and was known to smoke, drink, and do drugs. After sowing her wild oats at such a young age, Bijou became more focused on her career, taking roles in Almost Famous and Hostel: Part II.