Remember When The Highwaymen Named the Greatest Country Songs of All Time in 1991?

The Highwaymen were likely the greatest country music supergroup of all time. Made up of icons Johnny Cash, Kris Kristofferson, Waylon Jennings, and Willie Nelson, The Highwaymen made waves in the 1980s and 1990s before coming to an end in 1996. With three albums and a musical collaboration clearly built on friendship and mutual admiration for one another, The Highwaymen have gone down in history as some of the best to ever do it. And, naturally, interviewers wanted to know what made them tick.

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The Highwaymen sat down with one such interviewer in 1991 while touring New Zealand. During the interview, the host asks the four superstar country icons what they consider the greatest country song ever made. Their answers might not surprise you at all… or surprise you quite a bit.

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Kris Kristofferson was the first of The Highwaymen to give his answer. He said that “Big River” by his friend and fellow Highwayman Johnny Cash was his pick for the greatest country song ever made. And yet, this 1958 jam leans more toward rockabilly than country.

“I’ve often thought that that may be the best song, country or otherwise,” Kristofferson said, as Cash sat beside him with an almost shy sort of grin.

When Cash’s turn came around, he named “I Love You Because” as his pick for the greatest country song ever written. That song was written by Leon Payne and recorded by countless musicians, from Cash himself to Elvis Presley. He sang a few lyrics in that iconic voice of his.

“Leon Payne wrote that,” said Cash.

Waylon Jennings was up next and named “Dreaming My Dreams With You” by Allen Reynolds as “one of the best song [I’d] ever heard.” That tune was not only covered by Jennings in 1978, but he named a whole album after the song.

Willie Nelson came in last with a total classic. And I’m surprised it took so long for someone to name it. He said that “I’m So Lonesome I Could Cry” by Hank Williams was the greatest country song ever written. I’m inclined to agree with that pick, though each member of The Highwaymen had fine picks as well.

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