16. Slick Rick
Throughout the mid-80s, Slick Rick—eyepatched and accented—appeared all over MTV's airwaves, rapping "La Di Da Di" and "The Show." He dripped gold and fur, an opulent man in a time of extravagance. In 1990, though, it all ended. Rick the Ruler shot two men (one of them his cousin-slash-bodyguard) in revenge for an attempted shooting on his own life.
Prison can stop a career arc real quick, though not in this case: four years after his release, he put out his fourth album—1999's The Art of Storytelling—which quickly went gold. No, it wasn't the shooting or jail that did him in, but rather the deportation issues that stemmed from it. For years, Slick Rick battled the feds over whether he could live and work in this country, biding his time in Rikers while it was all figured out. (In 2008, New York's governor David Paterson pardoned his murder, which has allowed him to stay.)