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Hottest Artists on Tour: Madonna, Taylor Swift, Lady GaGa, Lil' Wayne, AC/DC,

Worst Pre-Fame Jobs: No. 24

Kenny Chesney: Valet

If every waiter in Nashville is a struggling songwriter, every valet is probably a struggling singer. Chesney might be the most famous to hold the position, but what goes around comes around: Among the valets to whom Chesney has handed his own keys is 'Stealing Cinderella' singer Chuck Wicks.

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