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"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.[1]


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.[2]

"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."

— Jimmy Webb, on the song: "The Highwayman".[3]

Webb's lyrics allude to the life of hanged highwayman Jonathan Wild,[4] the "sailer's graveyard" near Cape Horn, and the deaths of over 100 men during the Hoover Dam construction near Boulder City, Nevada.

He first recorded it for his 1977 album El Mirage, released that May.

Glen Campbell version[edit]

Webb then brought the song to Glen Campbell, who recorded it in 1978. But his record label, Capitol Records, wanted him to go in a different direction and record music like the group The Knack.[5] Campbell wanted to release the song as a single, but Capitol refused.[6] After recording 30 albums for the only record label he had worked with since 1962, Campbell got up and left the main studios of Capitol, never to return. Although he would record three more albums with Capitol, the relationship was at an end.[7] After disagreeing with the label, he released the song on his 1979 album Highwayman, released in October.

The Highwaymen version[edit]

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

Campbell then played the song for 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".[1] 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.[8] 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.[9] 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.[8] 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).[10] 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.[11] It finished 1985 as the number 5 country song of the year in terms of airplay.[12]

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 version by The Highwaymen earned songwriter Jimmy Webb a Grammy Award for 1985's "Best Country Song".[13]

Other Versions[edit]

Heavy metal band Iced Earth covered Highwayman on their 2014 album, Plagues of Babylon.

Finnish rock musician Pate Mustajärvi recorded a Finnish-language version of the song for his album Ukkometso released in 2000.

Independent Americana/folk artist Jake Smith aka The White Buffalo covered Highwayman as "The Highwayman" and recorded his version in 2013.

Arbouretum covered the song on their 2011 album, The Gathering.

Norwegian Folksong singer Finn Kalvik made a version of Highwayman called "Fredløs". It was released in 1993.

Makem and Clancy covered the song on their album "We've Come A Long Way".


  1. ^ a b Hurst, Hawkeye. - "Waylon and Johnny Walk the Straight and Narrow Together". - Orlando Sentinel. - July 21, 1985.
  2. ^ Holmes, Peter. - "Jimmy Webb - The hot seat". - The Sun-Herald. - September 24, 2000.
  3. ^ Cooper, Peter. - "Webb a master at songwriting". - The Tennessean. - June 23, 2006.
  4. ^ Wikipedia Contributors. "Jonathan Wild". Wikipedia, The Free Encyclopedia. Wikimedia Foundation. 
  5. ^ Burnes, John. - "Campbell is Riding His Success Nicely". - St. Louis Post-Dispatch. - June 23, 1988.
  6. ^ "The Express: Legend Glen is no punk". - The Express. - December 29, 2008.
  7. ^ Hoekstra, Dave. - "Glen Campbell, The Zelig of Roots Music". - Chicago Sun-Times. - July 24, 2005.
  8. ^ a b Campbell, Mary. - "High-powered Highwaymen are musical outlaws". - Associated Press. - (c/o The Augusta Chronicle). - June 1, 1995.
  9. ^ Hurst, Hawkeye. - "Marty Stuart Has Come a Long Way to Just Now be Arriving". - Orlando Sentinel. - June 15, 1985.
  10. ^ Complied from data from Allmusic - allmusic.com and Billboard - billboard.com.
  11. ^ "Highwayman". - Hot Country Songs. - Billboard. - billboard.com.
  12. ^ 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.
  13. ^ "Highwayman". - Grammy Awards. - c/o grammy.com.

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