After Kris Kristofferson’s Death, Willie Nelson Is the Only Surviving Member of the Highwaymen
The Highwaymen, often called the Mouth Rushmore of outlaw country, was a supergroup comprised of four of the most iconic country music artists of all time: Kris Kristofferson, Willie Nelson, Johnny Cash and Waylon Jennings. They formed the group in 1985 and helped contribute to the outlaw country subgenre, which started in the ’70s. Sadly, after the recent death of Kristofferson, Willie Nelson is the only surviving member of the group at 91 years old.
For one magical decade, the Highwaymen recorded three albums together and had one No. 1 hit song called “Highwayman,” from their 1985 debut album of the same name. Hitting the stage together for the first time at Willie Nelson’s Fourth of July Picnic on July 4, 1985, they did not yet have a name for their group and were just going by Nelson, Jennings, Cash, Kristofferson for the first two albums. Eventually they decided to take the name of their popular single. While the group split in 1995 to pursue more solo opportunities and the declining health of Waylon and Cash, they did reunite between 1996 and 1998 to provide the voice and dramatization for the Louis L’Amour Collection, stories from American novelist Louis L’Amour.
How did the Highwaymen form?
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So, how did four amazing country superstars decide to form their own supergroup? Of course, all of them were already famous. The group was reportedly born from friendship. They had the idea while performing at a Cash Christmas television special in Switzerland. In between filming, they jammed out together and decided to record an album.
Cash’s son John Carter Cash once said, “It’s the honesty and the purity of that friendship that made the Highwaymen stand out. Individually, these gentlemen had their own style, their own thoughts, their own feelings, their own emotion. But they came together as friends, and that’s the unifying power of the Highwaymen.”
However, there was supposed to be a fifth member. Merle Haggard reportedly was asked to join the group. He said, “I turned it down because I said, ‘Hell, it will cut the money down so low so the four of you guys won’t even want to do it.’ But they did offer me a part.”
However, the group hit a few snags along the way. In 1990, the original members of a ’50s and ’60s folk group of the same name sued the four men. The suit ended up being dropped after it was determined that the original folk group owned the name and they would grant a nonexclusive, nontransferable license to the supergroup for the name. All’s well that ends well, and they performed together during a Hollywood show that same year.
Not only did the group sing together, but they all also appeared in one film together: the 1986 film Stagecoach. Stagecoach was the second remake of the 1939 film of the same name, based on a short story by Ernest Haycox. It was a TV movie starring Kristofferson as Ringo, Nelson as Doc Holliday, Cash as Marshal Curly Wilcox and Jennings as Hatfield.
When did members of the Highwaymen die?
Kristofferson died on Sept. 28, 2024, Cash died on Sept. 12, 2003, and Jennings died on Feb. 13, 2002. Following the deaths of Cash and Jennings, Kristofferson and Nelson reunited several times, often paying tribute to their late group members. The two recorded “Roll Me Up and Smoke Me When I Die” together in 2012 for Willie’s album Heroes, along with Snoop Dogg.
Kristofferson once said about the group, “Those tours and the records we made were a great time. I just wish I was more aware of how lucky I was to share a stage with those people. I had no idea that two of them would be done so soon. Hell, I was up there and I had all my heroes with me. These are guys whose ashtrays I used to clean. I’m kinda amazed I wasn’t more amazed.”
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In honor of the group and the men we have lost, jam out to their hit song that started it all … “Highwayman”:
Remind 
Kings Of Country
March 2022
From outlaws Willie & Waylon to the Man in Black, Johnny Cash, we have every tear in your beer covered
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