Johnny Cash, Willie Nelson, Waylon Jennings and Kris Kristofferson Share Their Favorite Country Music Songs Of All-Time

The highwaymen country music

Oh, what country music fans would give for the opportunity to have The Highwaymen back in one room together.

But thank heavens for archives that give us some small glimpses, including a 1991 interview with New Zealand broadcaster, Paul Holmes.

Holmes sat down with Willie, Waylon, Johnny and Kris for an exclusive prior to their overseas tour and asked them a few questions about working together, their love for America, and their upcoming live shows.

Holmes even addressed some baseless accusations that the men were only teaming up as The Highwaymen to drum up business they couldn’t get individually.

As the interview concluded, Paul brought out the big guns with his final question, asking the men to share their opinions on the best country songs to ever be written. The tone of the room became very solemn as the men considered countless songs:

“Just to finish this, the best country song you think was ever written.”

Country music lovers know how daunting a question this truly is, but when you ask four of the best in the business, there’s an added layer of injustice in the question. They themselves have written and recorded many of the longstanding “bests.”

But take it from The Highwaymen themselves, here are their standout favorites as of the year 1991, Kris leading it off:

“Ugh, maybe ‘Big River,’ I have often thought that may be the best song country or otherwise…

Again, I will add that this is probably the highest stakes environment to ever be asked your favorite country song, because right next to Kris was the man who wrote and recorded ‘Big River’ – Johnny Cash.

Johnny followed up:

“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 ‘I Love You Because’ … Leon Payne wrote that.”

To hear this one, you have to time travel to the 1960s in black and white.

But watching Jim Reeves sing the song in his soulful voice will make it easy to see why Cash was so drawn to it.

Waylon continued:

“One of the best songs I ever heard… Several people recorded it, I recorded it but I had nothing to do with it. It just says something I think is really great and that’s ‘Dreaming My Dreams…’”

In a 1984 live performance of the song, Waylon shared with the audience:

“I guess this is my favorite song I ever recorded.”

And finally, Willie Nelson:

“I think the best song I’ve ever heard, especially a country song, is ‘I’m So Lonesome I Could Cry,’ a Hank Williams song. One verse in particular I think is the greatest lines I’ve ever heard, ‘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.’

Hank recorded the song on a summer day in Ohio, 1949. It has been re-recorded many times in different styles, including renderings by Elvis Pressley and Johnny Cash.

In the following vocal from the ‘Health and Happiness Show’ in the same year of its recording, Hank Williams called the song one of his most requested by fans, as well as his own favorite song.

A beer bottle on a dock



A beer bottle on a dock