Willie Nelson is the last Highwayman. Waylon Jennings, Johnny Cash and Kris Kristofferson are gone, and the supergroup they formed in 1985 lives on in records, old broadcasts and one man who is still on the road at 93. The four of them played Willie’s Farm Aid benefit three times. But only one of those shows, on April 24, 1993, in Ames, Iowa, had all four of them standing on the stage together.
The other two times, somebody was missing. And the way each gap got filled says a lot about the song that held them together.
1985: Kris Had to Leave Early
The very first Farm Aid was held in Champaign, Illinois, in September 1985, just weeks after “Highwayman” had spent a week at No. 1 on the country chart. Kris Kristofferson played an early set that day but had to leave before the Highwaymen were due onstage later in the day. Glen Campbell stepped into the quartet in his place.
There was a quiet irony in that. Jimmy Webb wrote “Highwayman” in the 1970s, and Campbell recorded it as the title track of his 1979 album. In 1984, it was Campbell who played the song for Johnny Cash, who was then putting together an album with Willie, Waylon and Kris. So at Farm Aid, the man who had handed the song to the group got to sing it with them.
1992: “You’re Wearin’ All Black”
The Highwaymen came back to Farm Aid in March 1992, at Texas Stadium in Irving, Texas. This time, Johnny Cash was sick and could not perform.
Jimmy Webb happened to be backstage. Years later, he told No Depression that Willie walked up, explained that Cash was ill, and asked him to come out and sing Cash’s part. Webb was dressed in black that day, and Willie, as Webb remembered it, told him:
“you’re wearin’ all black, just go out there and they’ll think you’re Johnny Cash”
So the songwriter went out and sang his own song as one of the Highwaymen. Webb called it one of the great moments of his life, and he said he resisted the urge to do a Johnny Cash impression.
April 24, 1993: All Four in Ames
A year later, Farm Aid VI came to Cyclone Stadium at Iowa State University, the stadium now known as Jack Trice Stadium. It was the only time the benefit has been held in Iowa, and a crowd of around 40,000 turned out to raise money for America’s family farmers. Willie was just days away from his 60th birthday.
This time, nobody was missing. Johnny Cash, Willie Nelson, Waylon Jennings and Kris Kristofferson took the stage together and worked through a set that included “Folsom Prison Blues,” “Shipwrecked in the Eighties” and Guy Clark’s “Desperados Waiting for a Train.”
Before “Highwayman,” Cash spoke to the crowd. “We’ve had a pretty good run,” he said, and he told them the four of them had been across the country and around the world together. By then they had released two albums, Highwayman in 1985 and Highwayman 2 in 1990, and had toured Europe as recently as the spring of 1992.
Then came the song. “Highwayman” follows one soul through four lives: a highwayman, a sailor, a dam builder and, finally, a starship captain. On the record, Willie sings the first verse, Kris the second, Waylon the third, and Cash takes the last. Webb once said he never knew how they chose who sang which verse, but that “having Johnny last was like having God singing your song.” In Ames, after two Farm Aids with a stand-in, all four of the original voices were finally there to carry it.
Nobody Called It Goodbye
Nothing about that day was billed as a farewell, and it was not the group’s last show. A month later, on May 23, 1993, the four were photographed together onstage at Central Park SummerStage in New York. They went on to record a third and final studio album, The Road Goes On Forever, in 1995.
But Farm Aid’s own archive lists the Highwaymen’s appearances at 1985, 1992 and 1993, and that is where the list ends. Ames was the last time they played the benefit, and the only time all four of them did it together.
The Last Highwayman
Waylon Jennings died on February 13, 2002. Johnny Cash followed on September 12, 2003. Kris Kristofferson died peacefully at his home on Maui on September 28, 2024, at the age of 88.
Willie Nelson is now 93, and Farm Aid is still his. This September, his name was at the top of the lineup again, this time in Virginia Beach.
The Ames set did not stay in the vault. When Sony released the Highwaymen’s live box set, Live: American Outlaws, in 2016, the Farm Aid VI recordings were on it, including a track listed as “Intro / Highwayman.”