#9, Lil Wayne
Total Arrests: 4
Rap Sheet: At age 9, Lil Wayne became the youngest member of the rap label Cash Money Records and his debut album sold more than 1 million copies, but his musical career isn't the only thing that started early. In July of 2007, Lil Wayne, then 24 years old, was arrested after a performance in New York City for criminal possession of a weapon and marijuana. In October of that year, after a concert in Boise, Idaho, Lil Wayne was arrested on felony charges of possessing a controlled substance; the charges were later dropped. He was arrested again in January 2008 when Border Patrol pulled over his tour bus and found marijuana, cocaine, MDMA and tens of thousands of dollars in cash.