The idea of reincarnation hasn’t exactly pervaded country music through the years. But in 1985, a meditation on the evolution of one’s soul, penned by the great Jimmy Webb, had another chance at life after two previous incarnations. The group that brought it back into existence: the Highwaymen, the supergroup of Willie Nelson, Kris Kristofferson, Waylon Jennings and Johnny Cash.
The song about an outlaw, a seaman, a construction worker and a spaceman sounds like a weird update of the Village People’s origin story, but Webb actually wrote it for his El Mirage LP, released in 1977. In an interview with Billboard, Webb revealed that while he was in England, after a night of heavy drinking with friend Harry Nilsson, he had “a very vivid dream” in which he was a highwayman being pursued. Later in the dream, he was caught and sentenced to hang. “Up until then, I hadn’t thought much about past lives,” he said.
“Highwayman” returned in 1979 as the title track of a Glen Campbell LP. Although the album failed to chart and his version was not released as a single, the tune would routinely be featured in Campbell’s live concerts, just one of the many Webb compositions he would cover during his career.
In 1984, the song was reborn when longtime friends Nelson, Kristofferson, Jennings and Cash were taping a Christmas show in Montreux, Switzerland, organized by Cash. Although Webb had previously played Campbell’s version for Jennings, and Cash band member Marty Stuart had tried to get his boss to record it, it wasn’t until all four of the country giants heard the song together that they decided to not only cut it, but title their new collective “The Highwaymen.”
Released as a single in the spring of 1985, the quartet performed it live for the first time during Willie Nelson’s Fourth of July Picnic. A month later, on August 17th, the song topped the country chart for a single week. In September, with Campbell standing in for Kristofferson, the song was performed at the very first Farm Aid concert in Champaign, Illinois (watch the performance above). The Highwayman album also topped the charts and featured a second Top 20 single, their take on Guy Clark’s “Desperados Waiting for a Train,” along with versions of Bob Seger’s “Against the Wind,” Cash’s “Big River” and Woody Guthrie’s “Deportee (Plane Wreck at Los Gatos).”
The Highwaymen would release two more LPs: Highwayman 2 in 1990 and The Road Goes on Forever in 1995 (reissued in 2005 with a DVD and bonus tracks). In 1992, they returned to Farm Aid, with Jimmy Webb taking Cash’s place, to perform their Number One hit. A year later, at the same event, all four of the original members would reunite to perform this and several other songs.
As it turns out, the subject of reincarnation would make a pretty quick return to the country chart: In late 1986, Tanya Tucker notched a Number Two hit with “I’ll Come Back as Another Woman.”