Tennessee native Jessica Andrews was born December 29, 1983, into a musical family. She found out that singing was her best quality in a fourth-grade talent show: her version of Dolly Parton’s “I Will Always Love You” won the first prize and set her on a quite good path. Eventually, she caught the ears of Nashville, and by 1998, she had signed a recording contract with DreamWorks Records.

That year, Jessica unveiled her debut single, “I Will Be There for You” and then her next single, 1999’s “You Go First (Do You Wanna Kiss)”, both cracked the top 30 of Billboard magazine’s Country Singles and Tracks chart, setting Jessica on her way to country stardom at only 15 years old.