Emerging amid the late-1990s wave of female country artists who crossed into pop, Jo Dee Messina nonetheless drew her strongest support from country listeners. Born August 25, 1970, in Framingham, Massachusetts, she spent her childhood in the nearby community of Holliston. At eight she began singing in musical theater productions, yet country music captivated her four years later, leading her to embrace the Judds, Reba McEntire, and Dolly Parton. Live performances soon followed, and by sixteen she was appearing in local clubs backed by a rhythm section that included her brother and sister. At nineteen she relocated to Nashville seeking wider opportunities, regularly competing in talent contests for cash prizes. One victory earned her a recurring spot on the radio program Live at Libby's, which attracted the attention of producer Byron Gallimore and prompted him to assemble a demo. At that same time Gallimore was also working with a young Tim McGraw, and the two artists became friends. Backstage at one of McGraw’s shows, Messina encountered a Curb Records executive and lightheartedly remarked that the roster needed a redhead. Producer James Stroud, who had just auditioned her demo, immediately endorsed her, resulting in a Curb contract on which Gallimore and McGraw served as producers.
Her self-titled debut arrived in 1996 and yielded two Top Ten singles: “Heads Carolina, Tails California,” which peaked at number two, and “You’re Not in Kansas Anymore.” Strong sales paved the way for the career-defining follow-up, I’m Alright. Issued in 1998, the album made Messina the first female country artist to extract three multiple-week number-one hits from one project—“Bye Bye,” “I’m Alright,” and “Stand Beside Me”—while “Lesson in Leavin’” climbed to number two. Both the CMA and ACM recognized her in 1999. Her third album, Burn, ventured further toward pop in 2000, becoming her first chart-topping release and delivering the number-one single “That’s the Way.” Additional Top Ten entries arrived with “Burn” and “Downtime,” and the Tim McGraw duet “Bring on the Rain” also reached number one, pushing Burn past the million-copy mark. Late in 2002 she issued the holiday collection A Joyful Noise, and Curb followed months later with a Greatest Hits package drawn from just three studio albums. Her next proper studio effort, Delicious Surprise, finally appeared in 2005. Although she had already begun recording the project that became Unmistakable, only a few singles surfaced before the full album emerged in 2010. Her long association with Curb ended in 2012; the subsequent album Me, released early in 2014 on her own Dreambound Records label, was financed through Kickstarter.
