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10. Cameron Douglas
Cameron Douglas, the son of actor Michael Douglas and his former wife Diandra Morrell Douglas has been arrested for drug offenses at least three times. In 2010, he was given a 5 year prison sentence for selling methamphetamine from a high-end Manhattan hotel. After repeatedly violating prison rules by arranging for his lawyer to smuggle him drugs in jail, he was ordered to spend 2 years in solitary confinement and his prison sentence was nearly doubled.
