Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson were already country music legends when they decided to record together in 1984. But finding a song that suited four unmistakably different voices proved harder than anyone expected.
Then Marty Stuart brought a Jimmy Webb composition into the studio. It had four verses, four characters, and a history stretching back nearly a decade.
According to Marty Stuart, Johnny Cash listened to the recording, asked to hear it again, and made one request:
“I want that verse about the starship.”
That decision helped turn an overlooked song into one of country music’s most recognizable recordings.
It Started With a Dream in London
Years before The Highwaymen existed, songwriter Jimmy Webb was working on the 1977 album El Mirage, produced by George Martin.
During a stay in London, Jimmy Webb experienced an unusually vivid dream about being a highway robber pursued along an English road. Jimmy Webb later recalled waking up and going directly to a piano to write the first verse.
The remaining verses developed into stories about a sailor, a dam builder, and a future traveler aboard a starship.
Jimmy Webb recorded “Highwayman” on El Mirage in 1977, but the song attracted little commercial attention.
Glen Campbell, who had already enjoyed tremendous success with Jimmy Webb compositions, recorded a version for the 1979 album Highwayman. That recording also failed to become a major hit.
For years, the song remained largely overlooked.
Four Friends, Four Very Different Voices
In 1984, Johnny Cash invited Willie Nelson, Waylon Jennings, and Kris Kristofferson to Montreux, Switzerland, for a Christmas television special.
During their time together, the four musicians traded songs and discussed making an album.
The idea eventually became a recording project in Nashville, with producer Chips Moman overseeing the sessions.
But there was a practical problem. Johnny Cash had a commanding baritone. Willie Nelson sang with distinctive phrasing that rarely followed conventional patterns. Waylon Jennings brought a rougher, forceful delivery, while Kris Kristofferson approached songs with a songwriter’s conversational style.
Traditional four-part harmony was not an obvious solution.
Marty Stuart, then a member of Johnny Cash’s band, later recalled that the early sessions lacked a song capable of bringing everything together.
The Song Marty Stuart Remembered
Musician Carl Jackson had previously told Marty Stuart about Jimmy Webb’s “Highwayman,” which Glen Campbell had recorded.
Marty Stuart remembered the title and contacted cousin Marty Gamblin, who worked with Glen Campbell’s music publishing company.
Marty Stuart obtained a copy and brought the recording to Chips Moman and Johnny Cash.
The attraction was immediate from a musical standpoint: four separate verses could accommodate four different singers without forcing their voices into conventional harmony.
In Marty Stuart’s recollection, Johnny Cash wanted to hear the song again before choosing the final verse about traveling across the universe.
Jimmy Webb has also credited Glen Campbell with helping introduce the composition to the musicians and explain its musical structure. The various recollections differ in some details, but both Glen Campbell and Marty Stuart played important roles in the song’s journey.
Four Verses That Finally Found Their Singers
The eventual recording assigned each character to a different performer.
Willie Nelson opened as the highway robber. Kris Kristofferson followed as the sailor. Waylon Jennings portrayed the dam builder. Johnny Cash closed with the starship verse.
The arrangement allowed each artist’s recognizable voice to carry an individual story while remaining connected to Jimmy Webb’s central idea of a spirit continuing through different lives.
Jimmy Webb later explained that the composition was not simply about reincarnation, but also about the enduring human spirit.
The quartet recorded “Highwayman” in Nashville in December 1984, with Marty Stuart contributing guitar and mandolin to the album sessions.
The Song That Gave The Highwaymen Their Name
The album Highwayman was released in May 1985.
On August 17, 1985, the title single reached No. 1 on Billboard’s country chart. At the 1986 Grammy Awards, Jimmy Webb received Best Country Song for writing “Highwayman.”
The successful recording also supplied the name by which Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson would become collectively known: The Highwaymen.
Four established artists had found a way to sing together without surrendering the individual styles that made each one famous.
And it happened through a song Jimmy Webb had written years earlier, Glen Campbell had helped keep alive, and Marty Stuart had remembered at precisely the right moment.
Johnny Cash got the starship verse. The other three found their places in the story. And “Highwayman” finally found the four voices that would make the song famous.