Messina debuted in 1996 with the single “Heads Carolina, Tails California”. Her album was certifified Gold by the RIAA. Her second album, I’m Alright produced five Top 10 Country hits between 1998 in 1999 and sold over a million copies in America. Since her debut, six of her singles have peaked at #1 on the Billboard Country singles chart and five of her albums have received a certification by the RIAA or the CRIA.
She was raised in Holliston, Massachusetts, by Vincent and Mary Messina, and had two sisters, Terese and Marianne, as well as a brother named Vincent. Messina had a variety of Country music influences, which included Patsy Cline, Reba McEntire, and The Judds. She soon started performing live, and by age 16 she was playing local clubs with a rhythm section made up of her brother and sister. The family band played up until Messina was in her late teens.
Realizing that living in the Northeast would limit her chances of achieving Country music stardom, Messina moved to Nashville at age 19. To support herself, Messina worked various temp jobs, including computer programming and accounting. In her spare time, she entered talent contests around Nashville.
One win led to a regular gig on the radio show Live at Libby’s, which in turn caught the interest of producer Byron Gallimore, who helped her assemble a demo tape. Gallimore was also working with the young Tim McGraw around the same time, and Messina befriended him. Backstage at one of his concerts, Messina met an executive from his label, Curb, and jokingly suggested that they needed a redhead. With the help of fellow Curb producer James Stroud, Messina was then signed to the record label. Gallimore and McGraw would later become co-producers of Messina’s studio albums under Curb.