Country Music Memories: ‘Highwayman’ Hits No. 1 on Billboard

Thirty-seven years ago today (Aug. 17, 1985) was a significant day for the country music supergroup the Highwaymen, made up of Waylon Jennings, Willie Nelson, Kris Kristofferson and Johnny Cash. It was on that date that their debut single, “Highwayman,” soared to No. 1 on Billboard‘s Hot Country Songs chart.

“Highwayman,” written by Jimmy Webb, was previously recorded by both Webb and Glen Campbell, before the quartet — who named themselves after the hit single — made it the title track of their freshman album. Each member of the group sang a verse.

“After I recorded it, the song languished for years,” Webb tells Performing Songwriter. “Eight years later, Glen played it for Johnny Cash. He was making a quartet album with Willie, Waylon and Kris Kristofferson. There were four verses to “Highwayman.” Talk about predestination. I don’t know how they decided who would take which verse, but having Johnny last was like having God singing your song.”

Marty Stuart deserves at least some of the credit for the group recording “Highwayman”: Jennings, Nelson, Kristofferson and Cash were together in Switzerland, for a TV taping, when Stuart reminded Cash of the tune. Stuart later played guitar on the recording.

“Highwayman” became the Highwaymen’s only No. 1 song; their follow-up single, “Desperados Waiting for a Train,” peaked at No. 15. Less than one year after the song landed at the top of the charts, the album of the same name was certified gold, for sales of 500,000 copies. Webb also earned a Grammy Awards trophy, for Best Country Song, for “Highwayman.”

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