Founded in 1989 as a more bluegrass-oriented band with Maguire and Strayer—then going by their birth surnames of Erwin—along with Laura Lynch and Robin Lynn Macy, the band did not achieve mainstream success until Lynch and Macy left and were replaced by lead singer Natalie Maines.

Shortly after her joining, the band signed to Monument Records, releasing their breakthrough album Wide Open Spaces in 1998.

Both it and its followup, 1999's Fly, earned the group several Grammy Awards and chart singles.

A seventh, a version of the Fleetwood Mac song "Landslide", was also a Number One hit on the Adult Contemporary chart.

Several of their singles have crossed over to the Billboard Hot 100, with their highest-peaking there being the number 4, "Not Ready to Make Nice".