When Johnny Cash, Waylon Jennings, Willie Nelson and Kris Kristofferson released their first album together in May 1985, the second song on the record was “The Last Cowboy Song.” To a lot of listeners it sounded brand new, a slow, aching goodbye sung by four of the biggest voices country music ever produced.
But the song was not new to two of the men singing it. By the time the four of them gathered around it, Willie Nelson and Waylon Jennings had each already put “The Last Cowboy Song” on a record of their own. The Highwaymen version was the third time the song had been recorded in five years.
Willie Was There From the Start
“The Last Cowboy Song” was written by Ed Bruce and Ron Peterson. Ed Bruce recorded it first, for his self-titled 1980 album on MCA Records, produced by Tommy West. The album credits list it as a duet with Willie Nelson.
Willie did not take over the record. He came in as a guest, adding harmony and singing the final chorus alongside Ed Bruce. Ron Peterson has since recalled that the original was the first time the song was ever cut, and that Willie handled the last chorus and some of the harmony parts.
Released as a single in 1980, Ed Bruce’s version reached No. 12 on the Billboard country chart. That original runs well over four minutes, longer than any version that came after it.
A Songwriter Willie and Waylon Already Trusted
It made sense that Willie Nelson would lend his voice to an Ed Bruce song. A few years earlier, Ed Bruce and his then-wife Patsy Bruce had written “Mammas Don’t Let Your Babies Grow Up to Be Cowboys.” Ed recorded it himself first, and then Waylon Jennings and Willie Nelson turned it into a No. 1 hit in 1978.
So when “The Last Cowboy Song” came along, another Ed Bruce song about cowboys and the life they stood for, it was already close to home for both men.
Waylon’s Turn in 1982
Two years after Ed Bruce’s single, Waylon Jennings recorded “The Last Cowboy Song” for WWII, his 1982 album with Willie Nelson on RCA. On that record it is one of Waylon’s solo tracks, and a short one, barely over two minutes.
It was a quiet moment on a busy, uneven album, but some critics singled it out. A 1983 review in The Christian Science Monitor named it one of the most beautiful songs on the record, describing it as a song about the lost art of being a cowboy.
The producer of WWII was Chips Moman. That detail matters, because three years later, Chips Moman would be the man in the producer’s chair again.
Four Voices, One Chorus
In 1985, Chips Moman produced the first album by the four men who would come to be known as the Highwaymen. Every one of its ten songs was a cover. The record opened with Jimmy Webb’s “Highwayman,” and right behind it came “The Last Cowboy Song.”
This time the song was built for four voices. The chorus belongs to all of them, and it comes back again and again: at the start, after the second verse and after the third. In the closing stretch, Johnny Cash’s verse overlaps with the chorus and carries straight through to the end.
The song itself looks back at the American West as something already slipping away. It calls up figures from the old stories, including Lewis and Clark and Wyatt Earp, and follows a nameless cowboy who stands in for the values that were disappearing with that world. Sung by four men who had spent their careers being called outlaws and living legends, the song took on a new weight.
Behind them sat a deep band, including Marty Stuart on guitar and mandolin, Reggie Young on guitar and Mickey Raphael on harmonica.
A Song They Kept Singing
“The Last Cowboy Song” did not stay in the studio. When the Highwaymen played Nassau Coliseum in 1990, it was part of the set, and it appears on the concert film later released as The Highwaymen Live. Ed Bruce, for his part, counted the Highwaymen recording among the proudest cuts of his long songwriting career.
The Last Voice Still Singing
There is a quiet irony in how the story has played out. A song about the end of an era was sung by four men who have, one by one, left the stage. Waylon Jennings died in 2002. Johnny Cash followed in 2003. Ed Bruce, who wrote it, passed away in January 2021 at 81. Kris Kristofferson died in 2024.
Willie Nelson, the man who was there when the song was first recorded in 1980, is the last of the four still out on the road. At 93, he spent 2026 touring and releasing new music.
Do you remember the first time you heard “The Last Cowboy Song”? Was it Ed Bruce’s original, Waylon’s version or the four Highwaymen together?