It led to the American Country Music award for "Top Female Vocalist" and a long string of chart-topping songs.
Not bad for a self-proclaimed "persistent redhead," who moved from a small town in New England to Nashville when she was only 19 years old.
Messina visited The Saturday Early Show to perform songs from her latest project , "Jo Dee Messina: Greatest Hits." It includes four previously unreleased tracks, and debuted at number one on the Billboard Country Album Chart.
The 32-year-old singer's other notable songs include "I'm Alright," "Bye Bye," and "That's the Way." She was the first woman in the history of Billboard's Country Singles chart to have three consecutive multiple-week, No.1 hits.
Messina was raised by a single mother in Holliston, Mass., a blue-collar Boston suburb. The singer says she was performing in clubs in her hometown at the age of 13.
After graduating from high school, she left to pursue a music career. Messina walked up to a Curb Records executive backstage at a local Nashville event to proclaim, "What you really need over there is a redhead." With a little help from friend and label mate Tim McGraw, who co-produced her first album with Byron Gallimore, she was signed to Curb for her first record contract - leading to music success.
But everything wasn't golden for Messina. Her album fell from the charts, as some wondered if she was a "one hit wonder." Also, her road expenses had exceeded her income. She was on the verge of bankruptcy.
She bounced back from the bad times. "I'm Alright," released in 1998, was another hit for Messina. It was certified double platinum with four chart-topping hits and two that reached the Top 10.
Her third album, "Burn," also was a multi-platinum success.
Messina hopes to release a fourth album in the fall or early next year. For the first time, that album will include songs she wrote herself.