10. Nicole Richie
Nicole Richie, the daughter of legendary musician Lionel Richie, has had repeated issues with the law. Back in October 2002, she was arrested after a brawl at a nightclub in New York City. The charges were eventually dropped. In February of 2003, she was arrested in Malibu, California. The charges included driving with a revoked license and possession of heroin. Shortly after her arrest she entered rehab. She was sentenced to 3 years of probation in August.
Richie was arrested on December 11, 2006, by the California highway Patrol after she failed a sobriety test. She was pulled over after a motorist reported a Mercedes-Benz entering the freeway using an exit ramp. She admitted to officers that she had been using marijuana and taking Vicodin. She was sentenced to four days in jail, however she served less than 82 minutes because of overcrowding in the jail.