The group released three albums with its original lineup—Thank Heavens for Dale Evans (1990), Little Ol' Cowgirl (1992), and Shouldn't a Told You That (1993). With Martie playing the fiddle and mandolin and her sister Emily on the banjo, guitar, dobro, and bass, the Dixie Chicks became known for their instrumental prowess. Following the arrival of Natalie, the group signed with Monument Records and began to revamp its cowgirl image and sound, eventually emerging as sophisticated performers with a hit country single, "I Can Love You Better" (1997). The trio's debut album, Wide Open Spaces (1998), sold more than 12 million copies and was named best country album at the 1998 Grammy Awards. "There's Your Trouble" won the Grammy for best country group vocal performance.

The Dixie Chicks' genre-spanning versatility quickly attracted fans from outside country music. In 1999 they received Grammys for their second album, Fly (best country album), and the single "Ready to Run." Home (2002), a return to the Chicks' acoustic roots, was named best country album at the 2002 Grammy Awards, where the singles "Long Time Gone" and "L'il Jack Slade" also received awards.

In March 2003, Maines ignited a firestorm by declaring onstage in London that she was ashamed that U.S. Pres. George W. Bush was from her native Texas. Many country music radio stations and radio networks banned the group's music, and Maines received death threats. The Dixie Chicks maintained a relatively low profile until 2006, when they returned with a world tour and the release of Taking the Long Way. Several tracks, notably "Not Ready to Make Nice," responded defiantly to the group's detractors, and the album's sound, decidedly more rock than country, clearly signaled the Chicks' desire to move on to new musical possibilities and new audiences. The documentary film Dixie Chicks: Shut Up & Sing, released later that year, provided an intimate portrait of the group in the aftermath of Maines's controversial remarks. At the 2007 Grammy Awards, the Dixie Chicks became the first all-female group to win the top three honours: album of the year, song of the year, and record of the year.