The Highwaymen were a Country music supergroup composed of four of the genre's biggest artists well known for their pioneering influence on the outlaw country subgenre: Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson. Active between 1985 and 1995, these four artists recorded three major label albums as The Highwaymen: two on Columbia Records and one for Liberty Records. Their Columbia works produced three chart singles, including the Number One "Highwayman" in 1985.
While not credited as The Highwaymen, between the years of 1997 and 1999, Nelson, Kristofferson, Cash, and Jennings also provided the voice and dramatization for the Louis L'Amour Collection, a four CD box set of seven Louis L'Amour stories published by the HighBridge Company.
Besides the 4 members, only one recording vocal artist ever appeared on a Highwaymen recording: Johnny Rodriguez (Spanish vocal on 'Deportee', a Woody Guthrie cover, from "Highwayman").
"Highwayman" is a song written by American songwriter Jimmy Webb, about a soul with incarnations in four different places in time and history, a highwayman, a sailor, a construction worker on the Hoover Dam, and finally as a starship captain.
Webb wrote the song while in a London hotel suite. His suite included a piano, and after he woke up from a dream about being an English highwayman, he went to the piano and started writing the song.
- "I had a black cape and pistols, and I was definitely a bandit. A highwayman, as it were. I was being chased within an inch of my life by these grenadiers on horseback, and I knew for a fact that if they caught me, they were going to kill me."
Webb's lyrics allude to the life of hanged highwayman Jonathan Wild, the "sailer's graveyard" near Cape Horn,
and the deaths of over 100 men during the Hoover Dam construction near Boulder City, Nevada.
El Mirage, released that May.
Johnny Cash. Webb brought the song to Waylon Jennings in about 1981, but Jennings, having heard the Campbell version, said "I just couldn't see it then". Cash, Jennings, Willie Nelson and Kris Kristofferson were all together in Switzerland doing a television special and decided that they should do a project together.In 1984, while the four were recording, Marty Stuart again played the song for Johnny Cash, saying that it would be perfect for them, four verses, four souls, and four of them. Campbell then played the song to all four of them, and the quartet had the name for their new supergroup, The Highwaymen, the name of their first album, Highwayman, and the name of their first single. The four thought it was a perfect name for them because they were always on the road and all four had the image of being outlaws in country music. In their version of the song, each of the four verses was sung by a different singer: first Nelson, then Kristofferson, Jennings, and finally Cash. Their cover of the Webb song remains the most popular and widely known of The Highwaymen's songs, being their only song to reach number 1 ("Desperados Waiting for a Train" at number 15 is the next closest). The version by the quartet entered the Hot Country Songs Billboard chart on May 18, 1985, rose to number 1, and spent 20 weeks total on the chart. It finished 1985 as the number 5 country song of the year in terms of airplay.
The version by The Highwaymen earned songwriter Jimmy Webb a Grammy Award for 1985's "Best Country Song"