Kenny Chesney zips around stage like his boots are on fire, a practice he might have learned working as a valet before he made it big in Nashville. The singer was already 24-years-old when he signed his first record deal. He'd graduated from East Tennessee University with a degree in advertising, but had set his sights on songwriting. He held down a number of jobs (including telemarketer, mail room sorter) before 'In My Wildest Dreams' was released in 1994, but parking cars is his most noteworthy. Ironically, he once handed his keys to another up-and-coming country singer who held a valet position, Chuck Wicks.

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