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"Highwayman" is a song written by American singer-songwriter Jimmy Webb, about a soul with incarnations in four different places in time and history: as a highwayman, a sailor, a construction worker on the Hoover Dam, and finally as a captain of a starship. Webb first recorded the song on his album El Mirage, released in May 1977. The following year, Glen Campbell recorded his version, which was released on his 1979 album Highwayman. In 1985, the song became the inspiration for the naming of the supergroup The Highwaymen, which featured Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson. Their first album, Highwayman, became a number one platinum-selling album, and their version of the song went to number one on the Hot Country Songs Billboard chart in a twenty week run. Their version earned Webb a Grammy Award for Best Country Song in 1986. The song has since been recorded by other artists. Webb himself included a different version on his 1996 album Ten Easy Pieces, a live version on his 2007 album Live and at Large, and a duet version with Mark Knopfler on 2010 album Just Across the River.

Jimmy Webb version[edit]

According to Jimmy Webb, he wrote the song in London while he was finishing up work on his album El Mirage, which was produced by George Martin. After a late-night round of "professional drinking" with his friend Harry Nilsson, Webb went to sleep and had "an incredibly vivid dream":[1]

I had an old brace of pistols in my belt and I was riding, hell-bent for leather, down these country roads, with sweat pouring off of my body. I was terrified because I was being pursued by police, who were on the verge of shooting me. It was very real. I sat up in bed, sweating through my pajamas. Without even thinking about it, I stumbled out of bed to the piano and started playing "Highwayman". Within a couple of hours, I had the first verse.[1]

Webb included the phrasing in the line, "Along the coach roads I did ride" to convey a kind of "antique way of speaking".[1] Not sure of where the song was leading him, Webb realized that the highwayman character does not die, but becomes reincarnated, and the three subsequent verses evolve from that idea.[1] In the second verse he becomes a sailor, in the third verse a dam builder, and in the fourth verse Webb switches to future tense and the character becomes an astronaut who will someday "fly a starship across the universe divide".[1]

The song may have been influenced by the real-life hanged highwayman Jonathan Wild. The dam builder verse alludes to the deaths of over one hundred men during the construction of Hoover Dam near Boulder City, Nevada. Webb's version of the song was first released on the album El Mirage in May 1977.

Glen Campbell version[edit]

Webb then brought the song to Glen Campbell, who recorded it in 1978. His record label, Capitol Records, wanted him to go in a different direction and record music like the group The Knack.[2] Campbell wanted to release the song as a single, but Capitol refused.[3] After recording thirty albums for the only record label he had worked with since 1962, Campbell left the main studios of Capitol and never returned. Although he would record three more albums for Capitol, the relationship was at an end.[4] Campbell eventually released the song on his album Highwayman in October 1979.

The Highwaymen version[edit]

Single by The Highwaymen
from the album Highwayman
Released May 6, 1985
Recorded 1984
Length 3:06
Label Columbia
Writer(s) Jimmy Webb
Producer(s) Chips Moman
The Highwaymen singles chronology
"Desperados Waiting for a Train"

In 1984, Glen Campbell played the song "Highwayman" for Johnny Cash, who was making a quartet album with Willie Nelson, Waylon Jennings, and Kris Kristofferson. A few years earlier, Webb brought the song to Jennings, but Jennings, having heard the Campbell version, said "I just couldn't see it then".[5] The four were all together in Switzerland doing a television special and decided that they should do a project together.[6] While the four were recording their first album, Marty Stuart again played the song for Cash, saying it would be perfect for them—four verses, four souls, and four of them.[7] Campbell then played the song again, this time 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.[6]

In The Highwaymen version of the song, each of the four verses was sung by a different singer: first Nelson, then Kristofferson, then Jennings, and finally Cash. Webb later observed, "I don't know how they decided who would take which verse, but having Johnny last was like having God singing your song (laughs)."[1] 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).[8] 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.[9] It finished 1985 as the number 5 country song of the year in terms of airplay.[10]

Chart positions[edit]

Chart (1985) Peak
U.S. Billboard Hot Country Singles 1
Canadian RPM Country Tracks 1
Canadian RPM Adult Contemporary Tracks 19
Preceded by
"I'm for Love"
by Hank Williams, Jr.
Billboard Hot Country Singles
number-one single

August 17, 1985
Succeeded by
"Real Love"
by Dolly Parton and Kenny Rogers
Preceded by
"40 Hour Week (For a Livin')"
by Alabama
RPM Country Tracks
number-one single

August 24, 1985


The Highwaymen version of the song earned songwriter Jimmy Webb a Grammy Award for 1985's "Best Country Song".[11]

Other versions[edit]

"Highwayman" has also been recorded by numerous other artists. Irish traditional musicians Makem and Clancy covered the song on their album We've Come a Long Way in 1986. Norwegian folk singer Finn Kalvik recorded his version of the song, called "Fredløs", in 1993. Finnish rock musician Pate Mustajärvi recorded a Finnish-language version of the song for his album Ukkometso, which was released in 2000. The band Arbouretum covered the song on their 2011 album The Gathering. Canadian band Walk off the Earth covered the song in their 2012 album Vol 1. Independent Americana-folk artist Jake Smith, also known as The White Buffalo, covered the song in 2013. Heavy metal band Iced Earth also covered the song on their 2014 album Plagues of Babylon in the format of The Highwaymen with four different singers singing. In this case it is Jon Schaffer of Iced Earth singing Willie Nelson's part, Russell Allen of Symphony X singing Kris Kristofferson's part, Stu Block of Iced Earth singing Waylon Jennings' part and Michael Poulsen of Volbeat singing Johnny Cash's part


  1. ^ a b c d e f Hutchinson, Lydia (August 15, 2012). "Jimmy Webb's Story Behind The Highwayman". Performing Songwriter. Retrieved February 1, 2015. 
  2. ^ Burnes, John. "Campbell is Riding His Success Nicely". St. Louis Post-Dispatch. June 23, 1988.
  3. ^ "The Express: Legend Glen is no punk". - The Express. - December 29, 2008.
  4. ^ Hoekstra, Dave. "Glen Campbell, The Zelig of Roots Music". Chicago Sun-Times. July 24, 2005.
  5. ^ Hurst, Hawkeye. - "Waylon and Johnny Walk the Straight and Narrow Together". - Orlando Sentinel. - July 21, 1985.
  6. ^ a b Campbell, Mary. - "High-powered Highwaymen are musical outlaws". - Associated Press. - (c/o The Augusta Chronicle). - June 1, 1995.
  7. ^ Hurst, Hawkeye. "Marty Stuart Has Come a Long Way to Just Now be Arriving". Orlando Sentinel. June 15, 1985.
  8. ^ Complied from data from Allmusic - allmusic.com and Billboard - billboard.com.
  9. ^ "Highwayman". - Hot Country Songs. - Billboard. - billboard.com.
  10. ^ MacDonald, Patrick. - "Proud Time for Pop". - The Seattle Times. - December 29, 1985.
    — "Billboard's Ratings of 1985's Top Pop Music Artists". - San Francisco Chronicle. - January 1, 1986.
  11. ^ "Highwayman". - Grammy Awards. - c/o grammy.com.

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