2 of Willie Nelson’s Final Contributions to The Highwaymen

By The Highwaymen‘s second offering, The Highwaymen 2, six of the 10 tracks were originals by all four founding members, Johnny Cash, Kris Kristofferson, Willie Nelson, and Waylon Jennings. On the album, Nelson also wrote two originals, “Two Stories Wide,” drilling in the message of living in the moment because, as Nelson croons, Life’s too long to worry, and the closing “Texas,” an ode to his (and Kristofferson’s) home state.

Videos by American Songwriter

“I had three of my favorite people out there,” said Nelson in the 2016 PBS documentary
The Highwaymen: Friends Till the End. “It was some of the best times of my life.” 

The supergroup’s 1985 debut, Highwayman, topped the Country Albums chart, and the title track, a cover of a 1977 Jimmy Webb song, went to No. 1, while their second album, Highwayman 2, peaked at No. 4.

When asked in 1991 if he thought the Highwaymen would work out when they first formed, Nelson joked, “I really didn’t know how much fun we’d all have out there together, because we all have egos as big as our buses. And I didn’t really know how we were all going to fit on one stage. As it turned out, it’s been fairly decent. There have been no knifings or shootings or anything.”

Throughout the band’s 10-year run, Nelson contributed original songs he wrote specifically for The Highwaymen, along with others he revisited from earlier in his career, through the group’s third and final union, The Road Goes On Forever, in 1995.

“The End of Understanding”

By the end of their run, Nelson contributed one last song to The Highwaymen’s third and final album, The Road Goes on Forever, a rerecording of his 1967 song “The End of Understanding.” Produced by Chet Atkins, “The End of Understanding” was released on Nelson’s sixth album, The Party’s Over and Other Great Willie Nelson Songs.

“Pick Up the Tempo”

Another Nelson song with the Highwaymen resurfaced a decade later on the 2005 reissue of The Road Goes on Forever, a rerecording of the 1974 Nelson-penned “Pick Up the Tempo,” originally recorded on This Time, Jennings 1974 album, which was co-produced with Nelson.

Though the Highwaymen came to an end after The Road Goes on Forever, its members continued on solo. Jennings died of complications from diabetes in February 2002, and Cash followed in September 2003 from diabetes complications. Kristofferson later died in 2024 at age 88.

“If you just take the music part of it and go back to, you know, Waylon [Jennings] and Kris [Kristofferson] and John [Johnny Cash] and, you know, all of us working together, the Highwaymen,” said Nelson following Kristofferson’s death. “And then I am the only one left. And that’s just not funny.” 

Photo: Rob Verhorst/Redferns