DMX's legal struggles are epic, but not more so than his rap career. After serving his first two sentences around 2000 for possession of marijuana and driving without a license — X recovered with barely a beat missed. He released The Great Depression in 2001, and it became his fourth No. 1 entry on the Billboard charts and eventually went triple platinum. And in 2003, he became the first artist to have five consecutive No. 1's with the release of his Grand Champ.