The Dixie Chicks rose from relative obscurity in 1998 to become one of the most popular acts in contemporary country music. Their origins date back nearly a decade earlier, to 1989, when fiddler Martie Seidel and her banjo-playing sister Emily Erwin formed the group in Dallas with bassist Laura Lynch and guitarist Robin Lynn Macy; after getting their start on local street corners, the quartet soon graduated to clubs, receiving an enormous boost when Seidel earned third place honors at the National Fiddle Championships. Originally, the Dixie Chicks (their name inspired by the Little Feat song "Dixie Chickens") promoted a classic cowgirl image, complete with a sound inspired by raditional country, folk, and luegrass; they even titled their 1990 indie-label debut Thank Heavens for Dale Evans.

With 1992's Little Ol' Cowgirl, the Chicks began slowly moving toward a more contemporary sound, a transformation that in part resulted in the exit of Macy; with Lynch assuming lead vocal duties, the remaining trio resurfaced in 1993 with Shouldn't a Told You That. Shortly after the Chicks signed with Sony's newly revived Monument imprint in 1995, Lynch left the group as well -- according to a December 10, 1998, feature in the Dallas Observer, both she and Macy were likely victims of Seidel and Erwin's desire to foster a more youthful image; the magazine goes on to call the group "the country version of Menudo, hiring and firing based on age." Soon named as Lynch's replacement was then 21-year-old lead vocalist Natalie Maines, the daughter of steel guitar legend Lloyd Maines.