Video Resurfaces Of The Highwaymen Sharing Their Favorite Country Songs

The Highwaymen Revealed Their All-Time Favorite Country Songs In An Interview With Paul Holmes In 1991

In 1991, the members of The Highwaymen shared the titles of their favorite country songs during an interview with New Zealand broadcaster Paul Holmes. Beyond that, the songs they named were ones they believed were some of the best country songs ever written.

Willie Nelson, Waylon Jennings, Kris Kristofferson, and Johnny Cash formed The Highwaymen. Following Kristofferson’s death on September 28, 2024, Nelson is the last living member of the former country supergroup.

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As Marty Stuart once shared in a video about the story behind The Highwaymen’s formation, almost all of the artists were friends before they started singing together. But Nelson and Cash were practically strangers. They tried to record some duets together, but something was off.

That’s when Stuart brought Cash the song “Highwayman,” which was written by Jimmy Webb. Cash, Nelson, Kristofferson, and Jennings each sang a verse before uniting on the song’s final lines.

They struck gold. The track reached #1 on the country charts in the U.S. and Canada.

The singers formed The Highwaymen and released three studio albums over the course of their ten-year run. The four men became even closer friends and had the utmost respect for each other.

That was obvious during their interview with Holmes about their favorite country songs. Kristofferson, who answered the question first, named Cash’s “Big River” as his pick.

“I’ve often thought that that may be the best song, country or otherwise,” he said.

Kristofferson also recited a few lines of “Big River” at Holmes’ request.

The Story Behind Johnny Cash’s “Big River”

“Big River” was written solely by Cash. He released the track as a single in 1958, and it reached the fourth spot on the Billboard Hot Country Singles chart. It also crossed over to claim the 14th spot on the all-genre Billboard Hot 100.

The song tells the story of lost love, with some of the lyrics being:

“Now I taught the weeping willow how to cry, cry, cry. And I showed the clouds how to cover up a clear blue sky. And the tears that I cried for that woman are gonna flood you Big River. Then I’m gonna sit right here until I die.“

One verse was scrapped from the recorded version of “Big River.” But Cash often included the extra verse in his live performances.

Many artists have covered “Big River” over the years, including Bob Dylan, Hank Williams Jr., and The Highwaymen themselves.

Which Songs Did The Other Highwaymen Name As Their Favorites?

Cash felt honored and “overwhelmed” when Kristofferson named “Big River” his favorite country song.

For his part, Cash said he believed the best country song ever written was “I Love You Because.” The track was written by Leon Payne and recorded by artists such as Elvis Presley, Jim Reeves, and Cash.

As for Jennings, he named “Dreaming My Dreams with You” as “one of the best songs [he’d] ever heard.” Allen Reynolds wrote the song, which has been covered by artists such as Jamey Johnson, Martina McBride, and Jennings. In fact, Jennings named his 1978 album after the song.

Nelson was the last Highwayman to share his favorite country song. He named Hank Williams’ “I’m So Lonesome I Could Cry.” Nelson closed out the interview by sharing some of his favorite lyrics from the song.

Watch The Highwaymen discuss their favorite country songs in the video below. Their discussion starts around the five-minute mark in the video, but the whole conversation is worth watching.