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100 Greatest Country Songs of All-Time: Part 8 (#30-21)

9/22/2019

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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:
​

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.

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: Kenny Rogers

30. "East Bound & Down" by Jerry Reed (1977)

Jerry Reed’s “East Bound and Down” is one of the songs of the ‘70s. It’s one of those rare songs that is just *perfect.* As in, I wouldn’t change a single thing about it. The chorus just begs to be sung out at the top of your lungs, and the driving guitar literally gives you a ride down the highway in the passenger seat of a Burt Reynolds-driven Trans Am. An iconic song fitting of such an iconic movie in “Smokey & the Bandit.” NK

29. "Hello Walls" by Faron Young (1961)

Truth be told, “Hello Walls” will always shine more of a spotlight on its writer, Willie Nelson, than its singer, Faron Young, but that’s not to discount Young’s ability as an artist. In fact, the two artists helped one another during this time – Young, the still budding honky tonk superstar influenced by Hank Williams, found his biggest hit through “Hello Walls,” the tune that also helped launch a young Nelson’s career into the spotlight. On that note alone, this song would naturally make a list of this caliber, though there’s always been something strangely appealing about a song where the narrator has a subdued, one-sided conversation with himself. If it weren’t so damn catchy, you’d swear it’s one of the saddest country songs you’d ever heard, and that’s saying something. ZK

28. "Seminole Wind" by John Anderson (1992)

Rarely in the history of country music has there ever been a song that served as a protest song and a socially conscious one as John Anderson’s 1992 top-five country hit “Seminole Wind.” The song told of the plight of the Florida Everglades, from Anderson’s home state, and how one of America’s greatest pieces of nature was being destroyed for profit. The soft piano and fiddle that opens the track gives it the dire feel it deserves and the song finishes out with the same while in between delivering a nice country-rock flavor while Anderson sings of the atrocities happening “in the land of the Seminole.” JS

27. "The Gambler" by Kenny Rogers (1978)

The setting? “A train bound for nowhere.” The time? Late at night. The year? Unknown. Tell me those elements don’t make a classic country song, and I’ll call you a liar. Kenny Rogers has always been one of those great artists that can tell a story like few others. He draws you in and dispenses words of wisdom or advice, none greater than “The Gambler.” I can’t imagine any other artist doing the Don Schlitz-penned song justice. Some songs are just meant for an artist, and “The Gambler” was meant for Kenny Rogers. NK

26. "On the Other Hand" by Randy Travis (1986)

If you’ve read Randy Travis’s excellent new book, Forever And Ever, Amen, you know how much of a struggle it was to release a song like this in the mid-’80s. Yet it’s because of that struggle that Travis is hailed as a hero today, a performer who released a stone cold country song at a time when the industry didn’t know what to do with itself (it was still dealing with the aftermath of the “Urban Cowboy” movement, in a large respect). As great as the song is on its own, it was like a wake-up call for the industry, and a defiant proclamation from its singer that he wanted to be a country music singer, dammit! But that song sure is a goldmine on its own, featuring one of the simplest, yet best hooks the genre has ever heard, and laying down its case for why it’s a classic all on its own. As George Jones once said, he was so excited to hear this song he urged people to pick up a copy of Travis’s debut album, Storms Of Life. That’s a good enough reason for me to put this song here. ZK

25. "Guitar Town" by Steve Earle (1986) 

Sometimes I wish I were alive in the summer of 1986 (I would be born the following year) to see and hear the revolution that must’ve been Steve Earle’s “Guitar Town.” The song, which would be the second single off Earle’s debut album of the same name, would become the singer-songwriter troubadour’s highest charting single of his career at No. 7. With its throwback guitar sound, and one of the greatest solos in country music history, and a devil may care attitude of life on the road it served as a message that country-rock hadn’t died off with the end of the ‘70s. JS

24. "Midnight in Montgomery" by Alan Jackson (1992)

Tributes to past musical heroes, while potent, are fairly hard to frame as anything other than a love letter from a fan. “Midnight In Montgomery” defied the concept, turning a tribute to Hank Williams Sr. into an actual story. Sure, it derives its concept from David Allan Coe’s “The Ride,” but Alan Jackson strips away the surprise bombast for something more eerie and everlasting – the young, budding country artist stops to pay respects only to be visited by the ghost of Williams himself. It’s the little details that have always made “Midnight In Montgomery” stand out, from one of the best pedal steel riffs ever in a country song to the lyrical odes; the artist is on his way to a show on New Year’s Eve, and even in death, Williams appreciates the fans who stop to pay their respects, but the company will never be enough to satisfy that aching loneliness he carried with him when he was alive. ZK

23. "Streets of Bakersfield" by Dwight Yoakam & Buck Owens (1988)

One of the great things about Dwight Yoakam when he burst upon the scene in the mid-‘80s was that he had modern day coolness about him, but also paid homage to the Bakersfield sound of the past that inspired him – no more so than to his obvious hero Buck Owens. Potentially my all-time favorite country music collaboration is Yoakam and Owens cutting “Streets of Bakersfield” together for Yoakam’s 1988 album Buenas Noches from a Lonely Room, which became a No. 1 hit. The song was written by Homer Joy and released as a single, to shockingly little success, by Owens in 1973. “Streets of Bakersfield” features one of the all-time great country choruses in: “You don’t know me but you don’t like me/You say you care less how I feel/But how many of you that sit and judge me/Ever walk the streets of Bakersfield?” This one’s cool as hell. JS

22. "Guitars, Cadillacs" by Dwight Yoakam (1986)

Man, what I’d give to have been around in 1986 when Dwight Yoakam burst out of the gates with an update of rockabilly and the Bakersfield Sound all thrown into one with some modern flare on “Guitars, Cadillacs” from his debut album Guitars, Cadillacs, Etc., Etc. The song, which went to No. 4 on the country charts, was Yoakam showing the mainstream of country music that he was a rebel and was going to do things his way – and all these years later he’s still doing just that. Yoakam’s sound is throwback, but cool and this song which Billboard’s Larry Flick called “a pure hillbilly delight” sounds as good as it did more than 30 years ago when it debuted. JS

21. "The Devil Went Down to Georgia" by Charlie Daniels Band (1979)

“The Devil Went Down to Georgia” seems like a song that could’ve been passed down generation to generation with Charlie Daniels providing a new rendition. But it’s an original, with a few elements of Southern folk-lore thrown in. The Devil plays first in the fiddle matchup, giving Johnny a tune more aligned with the disco of the era. Flashy but unsubstantial. Then Johnny goes and blows the Devil out of Georgia with a few Southern traditional standards. “I done told you once you son of a bitch, I’m the best that’s ever been...” It’s an iconic piece of country music. NK
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