, No. 52 in Best Western: Ed Bruce and Ron Peterson’s song, the original Highwayman album, and official audio.){kind=link}
No. 52 in our Best Western Songs countdown. The Highwaymen’s “The Last Cowboy Song” brings four distinctive country voices to a reflection on the passing of the cowboy era. Willie Nelson, Johnny Cash, Waylon Jennings, and Kris Kristofferson give the 1985 recording the feeling of old friends looking back together.
The song on Highwayman
Ed Bruce and Ron Peterson wrote “The Last Cowboy Song.” The official Johnny Cash song page credits E. Bruce and R. Peterson and identifies Highwayman as its parent album. Released by Columbia in 1985, the album brought the four singers together on a collection of songs with a strong storytelling character.
Chips Moman produced the recording. The Columbia recording credits displayed by Qobuz list all four singers as performers on the track and confirm Moman’s production credit. “The Last Cowboy Song” is the second selection on the original ten-track album, immediately after “Highwayman.”
A farewell to a changing West
The song looks at the distance between the cowboy of legend and a modern world with fewer open spaces. Everyday work sits beside memories of frontier adventure, creating a sense that an entire way of imagining America is slipping into the past.
Its references draw on Western storytelling, art, and popular memory. They work as a collage of the cowboy legend, rather than a literal account of one man’s life. That broad perspective gives the song its elegiac mood: the loss is cultural as well as personal.
Four voices sharing the same trail
The appeal of this performance lies in the contrast among the singers. Their individual tones remain recognizable, yet the shared refrain gives the song a collective weight. It feels like a conversation among men who understand the affection behind the Western image.
The arrangement leaves room for that character to emerge. The performance does not need to rush its farewell; the melody and the blend of voices carry the feeling. Within Highwayman, it sits naturally beside other reflective story songs, including “Desperados Waiting for a Train” and “The Twentieth Century Is Almost Over.”
The Western Writers of America list reproduced by Dave’s Music Database places the Highwaymen’s 1985 recording at No. 52. Continue with the preceding selection, John Denver with Emmylou Harris’s “Wild Montana Skies,” or revisit the group’s “Highwayman.”
Listen to “The Last Cowboy Song”
Hear the studio recording below, supplied by Columbia Nashville on the Highwaymen’s official artist channel.