In December 1984, Johnny Cash and Willie Nelson spent two days in Chips Moman’s Nashville studio trying to make a duet record work. It never did. Then Marty Stuart, the 26-year-old guitarist in Cash’s road band, walked into the control room with a tape of Jimmy Webb’s “Highwayman,” a song Glen Campbell had recorded years earlier and Waylon Jennings had already turned down. Within days, it belonged to four of the biggest names in country music.
A Hotel Room in Montreux
The idea started far from Nashville. In November 1984, Cash flew to Montreux, Switzerland, to tape his annual CBS Christmas special, Johnny Cash: Christmas on the Road. He brought friends: Willie Nelson, Waylon Jennings, Kris Kristofferson, Jessi Colter and June Carter Cash, with Marty Stuart on guitar.
Waylon later wrote in his 1996 autobiography that once the day’s work on the special was done, the men started trading songs in the hotel. Someone said what musicians always say in rooms like that: they ought to make an album together. Waylon noted that the idea usually dies once everyone goes home. This time it held.
Stuart remembered that hotel guitar pull as the standard for everything that followed. He said the magic in that room was something you could feel in the air.
Two Days That Went Nowhere
The timing mattered more for Cash than for anyone. By the mid-1980s his records were no longer selling the way they once had, and Stuart has said Cash was discouraged. Montreux gave him his first glimmer of hope in a long time.
Back in Nashville, Moman, who had produced some of Willie’s records in the early 1980s, suggested starting with a Cash and Nelson duet album. The two men gathered songs quickly and went to work. After two days, Stuart said, nothing they had cut really mattered.
Their voices were so polar opposite.
Willie’s loose, behind-the-beat phrasing and Cash’s low, square-shouldered baritone did not blend.
A Tape From Glen Campbell’s Publisher
Stuart had a song in the back of his mind. His friend Carl Jackson, a banjo and guitar player who had worked with Glen Campbell, kept telling him about a Jimmy Webb song Campbell had recorded called “Highwayman.”
Stuart also had a family connection. His cousin, Marty Gamblin, ran Glen Campbell’s publishing company. During a break in the sessions, Stuart called Gamblin, asked for a copy of the song, and went to pick it up.
He carried the tape into the control room and told Moman and Cash to listen. His argument was simple. The song had four verses. There were four men. Nobody would have to harmonize with anybody. Cash asked him to play it again.
Cash Claims the Starship
Webb’s song follows a single soul through four lives: an outlaw on the coach roads, a sailor on a schooner, a laborer on a great dam, and finally the captain of a starship. Cash heard it and claimed the last verse. According to Stuart, nobody argued.
On December 6, 1984, Cash, Nelson, Jennings and Kristofferson recorded “Highwayman” at Moman’s studio, with Stuart playing on the session. Willie sang the highwayman. Kris sang the sailor. Waylon sang the dam builder. Cash closed it as the starship captain.
Not every account of the song’s path is identical. Webb has said it was Campbell who played the song for Cash. Stuart’s version, told in several interviews, puts the tape in his own hands. Both men agree on the result.
The Song Waylon Had Passed On
Webb wrote “Highwayman” in London in 1977, while finishing his album El Mirage with producer George Martin. After a long night of drinking with Harry Nilsson, he dreamed he was an outlaw on horseback, pistols in his belt, running from lawmen who meant to catch him. He woke up sweating, went to the piano, and had the first verse within a couple of hours. Only later did he realize his highwayman does not die. He comes back.
Campbell recorded it and made it the title track of his 1979 album, but it never broke through. Webb also brought the song to Waylon Jennings a few years before the Highwaymen sessions. Waylon had heard Campbell’s version and said he just could not see it then. In 1984 he sang the third verse.
Four Verses, One Name
Columbia released “Highwayman” as a single on May 6, 1985. It entered the Billboard country chart on May 18, climbed to No. 1, and stayed on the chart for 20 weeks. The album, credited simply to Nelson, Jennings, Cash and Kristofferson, also reached No. 1 on the country albums chart. The four men took their group name from the song.
On July 4, 1985, they stood together on a stage for the first time, at Willie’s Fourth of July Picnic in Austin. The song later earned Webb the Grammy for Best Country Song.
Webb said he never knew how the four decided who would sing which verse. He called the fit a kind of predestination.
Having Johnny last was like having God singing your song.
For Stuart, the song opened a door. Around Columbia, he said, people started pointing him out as the kid who found that song for those guys. That attention helped him launch his own solo career.
Waylon Jennings died in 2002. Johnny Cash died in 2003. Kris Kristofferson died in September 2024. Willie Nelson, now 93, is the last of the four still on the road. He is the man who sang the first verse of the song a young guitarist carried into a Nashville control room in 1984.