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100 Greatest Country Songs of All-Time: Part 6 (#50-41)

9/21/2019

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by Nathan Kanuch, Zackary Kephart & Julian Spivey
When I heard that famed documentarian Ken Burns was putting together a definitive history of country music for an eight-part series on PBS I knew The Word had to compile a list of the 100 Greatest Country Songs of All-Time. I also knew that I wanted to collaborate on such a list with Zackary Kephart of The Musical Divide and Nathan Kanuch of Shore2Shore Country, whom I’ve worked with a few times on other collaborations. 
Methodology:
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When coming up with the idea to collaborate on a list of the 100 Greatest Country Songs of All-Time I asked Zackary Kephart of The Musical Divide and Nathan Kanuch of Shore2Shore Country to make up their own personal list of what they considered to be the 100 greatest country music songs of all-time. I had done the same.
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To get our definitive list I took songs that all three of us included on our lists and averaged those together. If a song was on all three lists, it automatically went to the top. So, if all three of us had a song ranked in the nineties on our list it could theoretically come out higher on the definitive list than a song that appeared very high on two lists but was left completely off the third (this did happen). Zack, Nathan and I were unanimous when it came to 32 songs.

This is where the methodology is a bit imperfect, but it’s the closest I could figure to get a definitive list of the greatest country songs of all-time.

If a song appeared on two out of the three lists, it would be averaged and slot in behind the 32 songs we all agreed should be in the top 100. There were 41 such songs.

The remainder of the list (27 songs) features songs that only appeared on one of the three lists and to get the most accurate ranking for the definitive list it was a “highest remaining song comes first” system. 
Picture: The Highwaymen - Willie Nelson, Kris Kristofferson, Johnny Cash and Waylon Jennings

50. "Much Too You (To Feel This Damn Old)" by Garth Brooks (1989)

“Much Too Young (To Feel This Damn Old)” was the very first taste we ever got of Garth Brooks and for my money he’s never recorded a better song. The song, co-written by Brooks and Randy Taylor, was the first single of his self-titled debut album in 1989 and is the tale of a cowboy who’s been trying to make a living on the rodeo circuit for years and not having much to show for it but a bruised body and a broken home life. It’s, without a doubt, one of the finest rodeo songs ever written and recorded. JS

49. "Highwayman" by The Highwaymen (1985)

This song is so good that it made Glen Campbell, who wanted to release the song as a single and was denied the chance, storm out of Capitol Records, never to return. There’s no doubt that Jimmy Webb is one of the finest songwriters ever, and this philosophical tale of reincarnation really did fit multiple voices best. Thankfully, the voices enlisted to tackle this were among country music’s best. Beyond the pure magnificence and scope of the song, the pure magnitude of this union can’t be overstated. Johnny Cash, Kris Kristofferson, Waylon Jennings and Willie Nelson formed the country super group, and they sounded like a polished group – not just some people thrown together as a marketing gimmick. Despite the obvious lapses in time between the character’s numerous times on earth, the verses all fit the singers perfectly. Nelson is the wild western cowboy who winds up paying a heavy price for his ways. Kristofferson is the dreamy-eyed sailor never content with letting the journey end. Jennings takes on the dangerous, reckless job because … well, someone has to, just as someone had to fight for artistic rights for all not long ago. And then there’s Cash just trying to find a place to rest his soul, especially with how many adventures he had in his time. And like they all say, they’ll be gone eventually (two of them already are). But they’ll be back again and again and again and again, if not in body or spirit, then certainly in the music they leave behind for all of us. ZK

48. "In Color" by Jamey Johnson (2008)

Jamey Johnson is one of country music’s finest songwriters of the last quarter-century and his 2008 Top 10 country hit “In Color,” which won him Song of the Year honors at both the ACM and CMA Awards is his career shining moment. “In Color,” a simple, mostly acoustic number co-written by Johnson, James Otto and Lee Thomas Miller, is the story of a young boy asking his grandfather about old black and white photos and listening to the stories of important moments in his grandfather’s life. The song was initially to be recorded by Trace Adkins, who gave Johnson the permission to record his own song first. It became the best mainstream country hit of the last dozen years. JS

47. "Lovin' Her Was Easier (Than Anything I'll Ever Do Again" by Kris Kristofferson (1971)

“I have seen the mornin' burnin' golden on the mountain in the skies/Achin' with the feelin' of the freedom of an eagle when she flies. Turnin' on the world the way she smiled upon my soul as I lay dyin'/Healin' as the colors in the sunshine and the shadows of her eyes...” Kris Kristofferson gave us the greatest ever opening verse to a song in those words right there. The imagery. The picture that Kristofferson paints. Pure poetry. The production is quiet and understated. We’re not sure if the two lovers are still together or if the narrator is fondly looking back at a previous relationship. The ambiguity of what Kristofferson gives the listener to work with is one of the many things that makes the song a classic. NK

46. "Mamas Don't Let Your Babies Grow Up to Be Cowboys" by Waylon Jennings & Willie Nelson (1978)

There are many fantastic lyrics in the legendary history of country music, but potentially my absolute favorite is: “them that don’t know him won’t like him/and them that do sometimes won’t know how to take him/he ain’t wrong/he’s just different/but his pride won’t let him do things to make you think he’s right” from “Mamas Don’t Let Your Babies Grow Up to Be Cowboys” by Willie Nelson and Waylon Jennings. I’m not sure there’s ever been a lyric that more explains the Outlaw Movement that those two essentially founded. The song, co-written by Ed and Patsy Bruce, was recorded for the collaborative 1978 Waylon & Willie album and would be one of the duo’s most successful duets of their friendship. JS

45. "Desperadoes Waiting for a Train" by Guy Clark (1975)

Guy Clark was proof that you could have a career outside of mainstream country music and Nashville and become a legend and an inspiration to many. His “Desperadoes Waiting for a Train,” that appeared on 1975’s Old No. 1, is potentially the greatest story song in the history of country music telling the story of an old man and young boy (possibly a grandfather and grandson) and the times they spend together. It’s the perfect example of Clark’s literary songwriting that’s had a huge mark on the Americana and alt-country subgenres of today. JS

44. "King of the Road" by Roger Miller (1965)

“Misunderstood” is a huge understatement when describing Roger Miller and his context in country music history. Not many people understood his goofball zaniness or that he had a much darker side. Music fans can certainly hear that side blatantly with “One Dyin’ And A Buryin’,” for instance, but “King of the Road” was another subtle portrait of Miller’s life. As someone who knew poverty all too well in his first 20 years of life, Miller combined that with his gypsy-loving lifestyle to create a child-like ode to adventure and not having to rely on anyone. In a word, it’s one of the catchiest ditties known to man with a surprisingly dark backstory. ZK

43. "Hurt" by Johnny Cash (2002)

Sure, it’s an obvious choice, but that doesn’t make it wrong. Johnny Cash’s commercial career declined by the early ‘80s, and by the early ‘90s, it was deader than a doornail. That is, of course, until producer Rick Rubin came along to make the American Recordings with Cash, giving his career not just a second wind, but a complete reinvention of what comprised a Johnny Cash song. During this time, Cash recorded plenty of unexpected songs from artists of all genres, but the one that sticks out the most is a cover of Nine Inch Nails’ “Hurt.” In a word, it was the masterpiece among many other masterpieces the two created together, and as for why it’s good … I mean, just listen to it. ZK

42. "Delta Dawn" by Tanya Tucker (1972)

The delivery Tanya Tucker gave us in the original recording of “Delta Dawn” showed the music world an artist mature beyond her years. The subject matter of the song is something we expect from an adult, not a 14-year-old. As far as the song itself: Incredible. The powerful song opens with a choir-like chorus letting the listener know he or she is in for one hell of a story (I’d love to see “Delta Dawn” turned into a movie). The subtle steel buried underneath Tucker’s voice lends itself perfectly to the heavy presence of the vocal, and the use of drums and harmonica complement the chorus so well. NK

41. "For the Good Times" by Ray Price (1970)

Ray Price’s 1970 performance of Kris Kristofferson’s “For the Good Times” might be the most beautiful sounding song to ever top the country charts, and surprisingly it was his first No. 1 in more than a decade. It’s essentially Price turning into Frank Sinatra for a song about lovers realizing their relationship has come to an end, but are trying to forget all the sadness of it for one last night together. It’s one of the most heartbreaking songs you’ll ever hear and helped, along with “Me & Bobby McGee” and “Sunday Morning Coming Down” to solidify Kristofferson as one of the world’s best songwriters. JS
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