1. Lil Wayne
Despite being one of the biggest names in rap, Lil Wayne found himself behind bars in 2010; proof that fame doesn’t shield you from the law. Sentenced to Rikers Island for a gun charge, he served time like anyone else, even ending up in solitary for having a charger and headphones. Fans were stunned that someone so iconic couldn’t dodge jail time, but maybe that’s exactly what made his story; and his comeback, even more powerful.