Date: November 2009

Lil Boosie was facing as many as 20 years with a five-year mandatory minimum for marijuana and gun charges in 2008. He took a plea deal for two years instead, which likely would have kept his time inside to around a year. While awaiting sentencing, though, he was put on electronic monitoring. When the judge found out Boosie's ankle bracelet registered numerous violations, his jail time was doubled.