Songfacts®:

• The Highwomen's namesake song finds the quartet reflecting on the experiences of women throughout history. Brandi Carlile takes the verse of a refugee killed escaping Honduras; Amanda Shires sings about a woman killed in the Salem Witch Trials; special guest Yola tackles the verse about a Freedom Rider; and Natalie Hemby reflects on the difficulties of being a female preacher.
• "Highwomen" is a reworking of Waylon Jennings, Willie Nelson, Johnny Cash, and Kris Kristofferson's country supergroup's theme song "The Highwayman." Carlile explained to Rolling Stone that on the original 1985 tune, the Highwaymen's characters all died doing things that men do. The Highwomen "rewrote it with fates that befell women: a doctor convicted of witchcraft; an immigrant who died trying to get over the border but got the kids over safe and sound; a preacher; and a freedom rider who gets shot."
• Songwriter Jimmy Webb wrote the original "Highwayman" and recorded it in 1977. Eight years later, the newly formed Highwaymen took the song to the top of the Country chart. Carlile told Beats 1's Zane Lowe that after completing their version, they asked Webb for his blessing.
  
  "We asked him if he wanted to contribute to the rewrite, and we told him what the concept of the movement and the band was," she recounted. "He wrote us back and said that he felt that it was spot on, and we were complimented by that to no end."
• Sheryl Crow is credited as she appears on the track as a background vocalist. Jason Isbell contributes Stratocaster guitar.
• The Highwomen debuted the song during their July 26, 2019 set at the Newport Folk Festival.