Massachusetts-born Jo Dee Messina, a protege of Tim McGraw, went from the top of the charts, to rock bottom, to the top again in just two years. The fiery redhead's 1996 debut single, "Heads Carolina Tails California," was a huge hit, but management problems brought her to the brink of bankruptcy. Her second CD brought her career back from the dead, spinning off a string of #1's and turning her into one of country music's hottest acts.
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