The favourite country songs of The Highwaymen: “That may be the best song, country or otherwise”
A collision of America’s favourite musical cowboys, the likes of which had never been seen before, The Highwaymen have gone down in history among the greatest supergroups to ever graced the airwaves, unified under a common adoration of country music and its enduring impact on the cultural landscape of the United States.
The Highwaymen first emerged in 1985, but the friendships forged within the group stretch back much further. Despite being one of America’s prevailing cultural contributions, it would appear as though the country music scene of the mid-20th century was fairly tightly-knit, with the likes of Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson rubbing shoulders long before Columbia Records unleashed Highwayman.
Cash and Kristofferson, for instance, first met in the corridors of Columbia, when the latter was working as a janitor and bumped into a pretty, worse-for-wear Cash at the peak of the Arkansas songwriter’s addiction struggles. Still, that didn’t stop the pair from striking up a friendship which quickly extended beyond the floor polish and bog brushes and landed onto some of the most iconic stages in the country world.
With Willie Nelson and Waylon Jennings entering the picture, the union was secured. Even though all four of them were huge names in the country realm, unlike other supergroups, though, there never seemed to be a power struggle within The Highwaymen. Their varied output eluded overlap just enough that instead of clashing, they created a beautiful blend of country influences that was greater than the sum of its parts.
During a tour of Australia in 1991, the superamalgam was given the platform to voice some of those enduring influences, when each member was asked to cite the greatest country song of all time. The respective answers affirm both the strong bonds between the members and the expansive sound at the heart of their output.
“Maybe ‘Big River’,” Kristofferson shared, kicking off the discussion by heaping praise onto his comrade, Johnny Cash, and his 1958 ode to the Mississippi River. “I’ve often thought that may be the best song, country or otherwise,” he added, to the stunned self-effacement. Admittedly, ‘Big River’ is a pretty solid choice as one of the greatest country songs ever written; it certainly stands among the crowning jewels of Cash’s beloved discography.
Quick to move things on, Cash himself chimed in, “The best [country] song that I think was ever written, I don’t know. I think probably ‘I Love You Because’”. Penned by Leon Payne back in the 1940s and popularised by Jim Reeves years later, the track offers a much more vulnerable, romantic view of the country spectrum, much like Jennings’ own pick for the greatest country song.
“One of the best songs I ever heard, and several people recorded it—I recorded it but I had nothing to do with it—it just says something that I think is really great, and it’s called ‘Dreaming My Dreams’,” Jennings shared, highlighting the song which formed the basis of his 1975 album. “It says no matter how bad things have been, in a relationship of any kind, you should come out of it with no bitterness and go ahead with your life.”
Nelson was the final member to contribute to this list, adding a mention for one of the genre’s defining stars. “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,” he said, before poetically noting, “One verse in particular I think is the greatest lines that I’ve ever is, ‘Silence of a falling star lights up a purple sky, and as I wonder where you are, I’m so lonesome I could cry’.”
Those four songs offer an unparalleled insight into the pillars of the country sound, going from early pioneers like Hank Williams to the revelation of Johnny Cash’s early efforts. With that plethora of influences at their core, The Highwaymen was bound to resonate across generations of country fans, as it does to this very day.
