14. James Brown
In 1988, Brown was involved in a high-speed police chase. He was ordered by the police officer to stop multiple times which he refused. Because of the incident, the singer was sentenced to six years and six months in prison. He was released after three years and stayed out of trouble for long ten years. Then, in 1998, he was charged with drug possession and was forced to enter a drug treatment program which lasted for 90 days.