Song · The Highwaymen
“Highwayman” by The Highwaymen
From the album Highwayman (1985)
“Highwayman” by The Highwaymen appears on 3 radio countdowns from 3 stations between 2010 and 2023. It was first released in 1985 on the album Highwayman. Its best result is #451 on the 90.9 The Bridge Top 909 Songs of the '80s.
The song came before the band. When Johnny Cash, Waylon Jennings, Willie Nelson and Kris Kristofferson joined forces in 1985, they named themselves after Jimmy Webb's "Highwayman" and made it the title track of their first album together. Webb's tale follows one soul through four lives across history, a highwayman, a sailor, a laborer on the Hoover Dam and at last a starship captain, and it takes four voices this seasoned to sell a reincarnation saga with a straight face.
Chips Moman produced and engineered it with a deep bench behind the stars, Mickey Raphael on harmonica, Marty Stuart on mandolin and Gene Chrisman on drums among them. Their version went to number one on Billboard's Hot Country Songs chart during a 20-week run and won Webb the Grammy for Best Country Song in 1986.
Written with AI assistance from RockLists chart data, MusicBrainz and Wikipedia.
RockLists rankings
Indie & Adult Alternative
All Rock Formats
All-time and decade countdowns
| Year | # | Station | Countdown | of |
|---|---|---|---|---|
| 2010 | 584 | WXPN | WXPN 885 Ultimate Road Trip Songs (2010) | 885 |
| 2021 | 451 | 90.9 The Bridge | 90.9 The Bridge Top 909 Songs of the '80s | 909 |
| 2023 | 756 | The Colorado Sound | The Colorado Sound Top 850 Songs of the 1980s | 850 |
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