She was sitting in with bands at Boston-area clubs by 14, her mother taking her, and had a band of her own with her brother and sister a year later. At 19 she left Holliston for Nashville. Curb Records released her self-titled debut in 1996, led by "Heads Carolina, Tails California," and it went gold. The second album, I'm Alright, is where the records fell: "Bye Bye," "I'm Alright" and "Stand Beside Me" each held No. 1 for multiple weeks in 1998, a first for a female country artist, on the way to nine No. 1 hits and 16 Top 40 songs overall, by her own count. The hits slowed in the early 2000s amid label disputes and personal struggles, and in 2017 she canceled dates to be treated for cancer, returning to the stage in 2018.
Cole Swindell's 2022 No. 1 "She Had Me at Heads Carolina" sent a younger crowd back to that first single, and she has made the most of the second look. Bridges, out June 5, 2026, is her first studio album in 12 years and the first she wrote nearly all of herself; David Spencer produced it, and Chris Lord-Alge, who mixed many of her '90s hits, mixed the lead single "Some Bridges." It deals with the loss and illness of the past decade. The Bridges Tour, billed as a 30-year celebration, opened June 11 in Columbus, Ohio, and has dates running into 2027. She played the Opry that June and sang "Some Bridges" on TODAY.