During her teens, she sang in country bands around her New England homebase. At the age of nineteen, she left for Nashville. For several years, Messina played local talent contests. By chance, she met an Curb Records executive at a Fan Fair and joked that she would be a good addition to the label. Producer James Stroud persuaded Curb that her demo tape was worth listening to and, by the end of 1994, she had signed to the record label.

Messina recorded her first album with producers Tim McGraw and Byron Gallimore over the course of 1995. The resulting record, Jo Dee Messina, was released in the spring of 1996 and was a hit upon its release. I'm Alright followed in 1998.