6. Snoop Dogg
There's almost a black hole sitting between Snoop's successes in 1993 and 2002. His Doggystyle, one of the finest rap albums ever, set him up to be Dr. Dre's protege; he was twenty-one years old. "Gin and Juice," "Nothin' But a G Thang," and "What's My Name" built up incredible momentum, which was then shot to shit when he got involved in a murder trial in 1994. (As if that wasn't enough to kill his work ethic, Tupac was shot dead a year later and Suge Knight had grown from mean to menace.)
Snoop needed to get out of there, and so he did, leaving Death Row for Master P's No Limit in 1998. While it was safer there, it's almost like it never happened. He sold a bunch of records, but at that time, it was impossible not to. It was only when he connected with The Neptunes for "From da Chuuch to da Palace," "Beautiful," and "Drop It Like Its Hot" that he became like a real person again. That's when people started appending "-izzle" to the end of their words; that's when he had a show on MTV; that's how he's able to afford all of that weed.