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10. Nelly. It's not fair to call Nelly washed up, but he's hardly on the vanguard of the rap game. And it's always better to reinvent oneself from a position of power, as it projects something less unseemly than bald desperation. Of all modern rappers, Nelly's shown the least fear of sing-songy rhymes, hails from Missouri (basically the south), released an album called Country Grammar, and has already collaborated with Tim McGraw. Put on a Stetson and meet us at the Opry, baller.
9. Ruben Studdard. Nashville goes apeshit for American Idol winners, as evidenced by the runaway success of Cary Underwood, Scotty McCreery, and even Kelly Clarkson in a scene-stealing cameo, to the point where Nashville Star was rendered instantly redundant. Studdard's AI championship hasn't exactly translated into success through more traditional musical channels. Time to hit the dirt road, big fella.
8. Leon Hendrix. Jimi's baby brother has nothing to lose, except everything.
7. Brandy. This teen once topped the pops and was Kobe Bryant's dream date to prom. Nowadays she's better known for having a brother who filmed himself boning Kim Kardashian, and would be lucky to land a gig putting on Rihanna's heel during a wardrobe change. The good news: She's already named for a drink that's sufficiently toxic to curry instant favor among bumpkin boozers. What's that equal? Mo' money for Moesha.
