The Dixie Chicks were founded by Laura Lynch on upright bass, guitarist Robin Lynn Macy, and the multi-instrumentalist sisters Martie and Emily Erwin in 1989. The Erwin sisters have since married and changed their names to Martie Maguire and Emily Robison, then Strayer. The four took their band name from the song and album Dixie Chicken by Lowell George of Little Feat, originally playing predominantly bluegrass and a mix of country standards. All four women played and sang, though Maguire and Robison provided most of the instrumental accompaniment for the band while Lynch and Macy shared lead vocals. Maguire primarily played fiddle, mandolin, and viola, while Robison’s specialties included five-stringed banjo and dobro.
In 1990, thanks to the generosity of Penny Cook, daughter of then Senator John Tower, who wrote them a check for $10,000 so that they could record an album, the Dixie Chicks recorded their first studio album, Thank Heavens for Dale Evans, named after the pioneering, multi-talented performer Dale Evans. They paid $5,000 for the 14-track album. The album included two instrumental tunes. In 1987, Maguire (still known then as Martie Erwin) had won second place, and in 1989, third place in the National fiddle championships held at the Walnut Valley Festival in Winfield, Kansas. A Christmas single was released at the end of the year – a 45 RPM vinyl record titled Home on the Radar Range, with “Christmas Swing” on one side and the song on the flip side named “The Flip Side”. The record titles were significant; during that period of time, the bandmates dressed up as “cowgirls”, and publicity photos reflected this image. However, even with an appearance at the Grand Ole Opry, with few exceptions, such as Garrison Keillor’s radio show A Prairie Home Companion, they didn’t get much national airplay.
The Dixie Chicks began building up a fan base, winning the prize for “best band” at the Telluride Bluegrass Festival and opening for established country music artists, including such big names in that genre as Garth Brooks, Reba McEntire, and George Strait.
In 1992, a second independent album, Little Ol’ Cowgirl, moved towards a more contemporary country sound, as the band enlisted the help of more sidemen, and developed a richer sound with larger and more modern arrangements. Robin Lynn Macy was not pleased with their change in sound, however. She left in late 1992 to devote herself to a “purer” bluegrass sound, remaining active in the Dallas and Austin music scenes. It was during this period that professional steel guitarist Lloyd Maines (who had played on both albums) introduced them to his daughter, Natalie, an aspiring singer. Lloyd Maines thought his daughter would be a good match to replace the departed Macy, and had passed along Natalie’s audition demo tape, which had won her a full scholarship to the Berklee College of Music, to both Maguire and Robison. Her distinctive voice was a match for Maguire’s soprano and Robison’s alto harmonies. As Maguire and Robison considered their options and the major record labels waffled over whether they should take a risk on an all-woman band, a few reviewers took note of their talents:
Some record label executives will be kicking themselves soon enough when the Dixie Chicks are queens of the honky-tonk circuit. If their show at the Birchmere last week was any indication, these Chicks have what it takes to make the big time, yet no major label has taken the plunge to sign them.
— Eric Brace, The Washington Post
Lynch, thrust into the role of sole lead singer on their third independent album, Shouldn’t a Told You That in 1993, was unable to attract support from a major record label, and the band struggled to expand their fan base beyond Texas and Nashville.
New manager Simon Renshaw approached music executive Scott Siman and he signed them to a developmental deal with Sony Music Entertainment’s Nashville division. The deal was finalized with Sony over the summer of 1995. The Chicks then replaced Lynch with singer Maines. Accounts of the departure have varied. At the time, the sisters stated that Lynch had been considering leaving the band for over a year, weary of touring, and hoping to spend more time with her daughter at home. She offered to stay for the first cuts on the new album for Sony, but the sisters thought it would send the wrong message to the label; they all agreed she would leave before the new album. In a later interview, Lynch said, “It can’t really be characterized as a resignation. There are three Dixie Chicks, and I’m only one.”By her own account Lynch has noted that she had no regrets about leaving.