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As a teen in Kennett, Mo., Nail fed a country music obsession by spending his lunch money on cassette tapes at Wal-Mart. "I probably had 400," recalls the crooner, now 28 and awaiting the 2008 release of his own CD. Among his songs: "Missouri," a personal ballad about a painful breakup that he actually wrote years ago. "Sometimes," he says, "you have to work up the courage to show your vulnerable side."