Maines's first commercially released work was background vocals on Pat Green's debut album, Dancehall Dreamer, produced by her father Lloyd Maines and released in 1995. At the end of 1995, at age 21, Maines joined the all-female country music band, the Dixie Chicks, which had been performing since 1989, but which had been unsuccessful in gaining more than local attention. Maines replaced founding lead singer Laura Lynch. She plays guitar and bass in concert in the band.  Maines co-wrote four tracks for the Dixie Chicks' first three albums, including the Billboard Hot Country Singles & Tracks chart number one hit "Without You" on Fly. Maines was a primary songwriter on all 14 tracks of the band's 2006 album Taking the Long Way which peaked on the Billboard 200 chart at No. 1. Taking the Long Way has the Billboard Hot 100 single "Not Ready to Make Nice", (Maines, Strayer, Erwin, Wilson) hitting No. 4 and for which the band won the songwriting Grammy Award, for Song of the Year. Maines considers the songwriting she did for Taking the Long Way "pure therapy" after the controversy that ensued over a comment Maines made from the stage in London that criticized U.S. President George W. Bush. "Everything felt more personal this time", Maines said about the album, "there's just more maturity, depth, intelligence. ... [These songs] feel more grown-up."  Maines collaborates with other musical artists, both as a member of the Dixie Chicks and an individual singer. The Dixie Chicks first worked with Sheryl Crow in 1999 while performing for the concert tour Lilith Fair. Since then, the Dixie Chicks have worked with Crow on her Sheryl Crow and Friends: Live from Central Park album, a Crow remixed version of "Landslide" performed by the Chicks, and the Dixie Chicks' song "Favorite Year" from Taking the Long Way. Maines has performed with artists including Pat Green, Charlie Robison, Yellowcard, Stevie Nicks, Patty Griffin, Neil Diamond, Eddie Vedder, Pete Yorn and Ben Harper.  Maines is a friend of Howard Stern and has made several appearances on his show.  On May 7, 2013, Maines released a solo album entitled Mother. This was Maines's first album since the Dixie Chicks hiatus started in 2007. The album was co-produced by Ben Harper. The album contains Maines's interpretation of several cover songs, including Pink Floyd's "Mother", Eddie Vedder's "Without You", and Jeff Buckley's "Lover, You Should've Come Over". She also sings about motherhood, feminism, and painful relationships.

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