With Kris Kristofferson’s recent passing, Willie Nelson stands as the last surviving member of the legendary country music supergroup, THE HIGHWAYMEN. The group was named after their signature song, “Highwayman,” which was written by country singer-songwriter Jimmy Webb.
In a special interview about Johnny Cash’s life, Stuart recounted how he played a pivotal role in the formation of the Highwaymen. He explained how in the 1980’s, Cash was feeling a bit down on himself because his music wasn’t performing as well as it used to. Stuart said that Cash got his “first glimmer of hope” in some time after performing a Christmas special with three guests: Willie, Waylon, and Kris. Most of the guys were already friends at the time except for John and Willie. Afterward, Stuart shared that Nelson’s producer, Chip Moman, proposed a duet album for Cash and Nelson to strengthen their bond. Anyone who has ever heard Nelson and Cash sing knows how distinct their voices are. That uniqueness clashed when the duo came into the recording studio, and Stuart said that the “magic” was lacking between them. “Their voices were so polar opposite,” Stuart said.
Eager to make the collaboration a success, Stuart recalled a song his friend Carl Jackson had mentioned: “Highwayman,” which had already been recorded by Glen Campbell. Luckily, Stuart had some connections in the industry. He managed to get his hands on the song.
Stuart came into the studio and played the song for Moman and Cash. He approached the two of them with a simple pitch, saying, “Listen, four verses, four guys, no harmony required.” Stuart was clearly referring to the legendary quartet: Cash, Nelson, Jennings, and Kristofferson.
The title track became a No. 1 hit on Billboard‘s Hot Country Songs Chart. Other notable tracks include their rendition of Guy Clark’s “Desperados Waiting for a Train.” From there, the group went on to release two more studio albums: Highwayman 2 and The Road Goes On Forever – all of which have gone down as singular and vital pieces of country music magic.
Their solo careers were so iconic that only their combined star power could even hope to outshine them. But, according to those closest to the foursome, their success was rooted in the admiration and love they shared for one another.