Jo Dee Messina is a chart-topping American country singer-songwriter whose late-1990s and early-2000s hits — including "Heads Carolina, Tails California," "Bye, Bye," and "I'm Alright" — helped define a generation of country radio. Born August 25, 1970, in Holliston, Massachusetts, she moved to Nashville at 19 and was discovered by Tim McGraw and producer Byron Gallimore.

Her 1996 self-titled debut album, Jo Dee Messina, introduced her with the breakout single "Heads Carolina, Tails California," which reached #2 on the Billboard Hot Country Songs chart. Her sophomore album, I'm Alright (1998), made her the first female country artist to score three consecutive multi-week #1 singles, with "Bye, Bye," "I'm Alright," and "Stand Beside Me" all topping the country charts and earning her the 1999 ACM Top New Female Vocalist award.