Jessica Andrews first displayed her knack for singing in fourth-grade when she performed Dolly Parton’s “I Will Always Love You” in a school talent show. Andrews was born and raised in Huntingdon, Tennessee and was steeped in country music from an early age. In her teens she could often be seen performing at fairs and carnivals but a meeting with Byron Gallimore pushed her into a more professional environment, recording for Nashville’s Dreamworks label.

Andrews released her debut, Heart Shaped World, in 1999 and followed it up with Who I Am two years later. Andrews had a number one country hit with the album’s title track and two years later she released her third album, Now, before she had even entered her twenties.