Wrecking Ball

Her 1993 album Cowgirl's Prayer had no top 40 singles and peaked at number 34 on the Billboard charts. Pitchfork's Allison Hussey recalled Harris saying, "It was obvious after all [the label's] effort that country radio was not interested in me." The label, Elektra, encouraged her to consider a producer, and she chose Daniel Lanois, who recorded her at his Kingsway Studios in New Orleans. Mark Howard engineered, and Trina Shoemaker worked on engineering and mastering.

Lanois wrote Where Will I Be and Blackhawk. Harris took Steve Earle's Goodbye, Julie Miller's All My Tears, which she had sung with Miller in 1993, Anna McGarrigle's Goin' Back to Harlan, Bob Dylan's Every Grain of Sand, Lucinda Williams's Sweet Old World, Jimi Hendrix's May This Be Love and Gillian Welch's Orphan Girl. Neil Young wrote the title song and sings harmony on it, and adds harmonica to Sweet Old World. She co-wrote Deeper Well with Lanois and David Olney, and Waltz Across Texas Tonight with Rodney Crowell. Larry Mullen Jr. of U2 plays drums on most tracks, and Kate and Anna McGarrigle sing harmony on the closing waltz.

The album reached number 94 on the US albums chart, number 58 in Canada and number 46 in the UK, and it won the Grammy for contemporary folk in 1996. AllMusic's Jason Ankeny called it "a hypnotic, staggeringly beautiful work". Hussey, reviewing it for Pitchfork in 2022, wrote that it is "a staggering work that defied expectations for what a middle-aged woman should be doing with her time". According to the Los Angeles Times, its production has been considered influential in establishing the Americana genre. It has been compared with Marianne Faithfull's Broken English and Johnny Cash's American Recordings.