Kris Kristofferson (Sterling Munksgard / Shutterstock)

The Songs The Highwaymen Thought Were The Greatest Country Song Of All Time

For those of you who love the music of Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson, The Highwaymen were a genuine treat. When the four of them joined forces to create that supergroup, fans rejoiced. They made some sublime tunes together. That, combined with their "outlaw" sensibility, was exceptional. Sadly, Nelson is the sole member of the group who is still living.

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As American Songwriter succinctly observed, "Other than their apparent musical talent, another facet that made the collaboration so illustrious was the fact that they were all friends." The natural camaraderie between the quartet of country music icons enlivened everything they did and heightened its authenticity. And when it came time for them to chose the greatest country song of all time, they did not hesitate.

The Highwaymen Gave A Rambunctious Interview On A New Zealand Talk Show In 1991

There was plenty of laughter and good-natured joshing during that interview on Holmes, hosted by Paul Holmes. He posed an interesting question to each of The Highwaymen - namely, what is the greatest country song ever? Cash, Kristofferson, Jennings, and Nelson forthrightly gave their expert opinions.

The Four Singers Discussed Their Picks For The Greatest Country Song Ever

Kristofferson said, "Maybe 'Big River.' I've often thought that might be the best song, the best country or otherwise." It was penned and recorded by Cash in 1958.

Then Cash himself took a crack at the host's challenging question. He modestly said, "Well, I'm overwhelmed because I wrote that song. The best song that I think was ever written, I don't know, I think probably, a country song... 'I Love You Because'."

Waylon Jennings was The Highwayman who plunged in next. "One of the best songs I ever heard, several people have recorded it, I've recorded it, but I had nothing to do with it, it just says something that I think is really great and that's called 'Dreaming My Dreams.' And it says no matter how bad things have been, in a relationship of any kind, you should come out of it with no bitterness."

Nelson took his turn last. "I think the best song I've ever heard, especially a country song, is 'I'm So Lonesome I Could Cry.' Hank Williams song, one verse in particular that is the greatest line I've ever heard is 'The silence of a falling star lights up a purple sky / And as I wonder where you are, I'm so lonesome I could cry.'"

There you have it. All four of The Highwaymen weighed in with their pick for greatest country song. Do you agree?