14. Lil Wayne
But despite selling over 1 million copies of his debut album at such a young age, Lil Wayne didn’t seem satisfied with his success. As he went along, he got arrested on multiple occasions for possession of weapons and drugs.
Lil Wayne first got arrested in 2007 after a live performance in New York for possession of marijuana and a weapon. Shortly after, he had another run-in with the law in Idaho for the same thing.
Then in 2008, his tour bus got searched, only for the Border Patrol to find cocaine, marijuana, MDMA, and a large sum of money in the rapper’s possession.
Total number of arrests: 4