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100 Greatest Country Songs of All-Time: Part 2 (#90-81)

9/15/2019

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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.

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: Garth Brooks

90. "Here in the Real World" by Alan Jackson (1990)

“Here in the Real World,” co-written by Alan Jackson and Mark Irwin, was Jackson’s first career hit topping out at No. 3 on the charts in 1990 and I contend is the best song he’s ever recorded. It’s a fantastic crying fiddle weeper about how relationships in the real world just aren’t as easy as they’re portrayed on the silver screen. Following in the footsteps of Randy Travis, Jackson was one of the major factors of a new wave of neotraditionalists of the time and “Here in the Real World” showed he was a force to be reckoned with. JS

89. "Blue Moon of Kentucky" by Bill Monroe and his Blue Grass Boys (1947)

It’s hard to believe that just one recording session helped launch an entire subgenre of music. “Blue Moon Of Kentucky,” in a nutshell, is remembered most famously for being one of many factors to kickstart what we call “bluegrass,’ but it’s also emblematic of what makes pure bluegrass music so pristine – Bill Monroe and his Blue Grass Boys’ high, lonesome vocal matched with an interweaving of beautiful banjo and mandolin picking along with the saw of the fiddle. Its influence is where it really makes its mark, but “Blue Moon Of Kentucky” is a beautiful song in its own right. ZK

88. "Wabash Cannonball" by Roy Acuff (1936)

Many of country music’s earliest recordings were actually folk standards originating sometime in the 1800s, with “Wabash Cannonball” being one of them. In truth, the legacy of “Wabash Cannonball” is where the real conversation with this song takes place. The Carter Family recorded their version of it, but it was Roy Acuff who made it into a smash single in 1936, earning the attention of the Grand Ole Opry and becoming one of its most beloved members of all time. If anything, “Wabash Cannonball” is partly responsible for helping to bring country music into the mainstream, and Acuff will forever be remembered as one of its greatest pioneers. ZK

87. "Wagon Wheel" by Old Crow Medicine Show (2004)

“Wagon Wheel” is a fascinating story of a song as it took more than a quarter century to complete. It began as a sketch of a song, really just a chorus, written by Bob Dylan in 1973. The song was given to Old Crow Medicine Show member Ketch Secor in the late ‘90s by fellow group member Critter Fuqua on a Dylan bootleg and Secor wrote a wonderful story of a hitchhiking journey down the Eastern Coastline around the chorus. You put the O.C.M.S. Americana bluegrass/folk feel to it and you have a modern classic. The song became a legend among the alt-country scene, but when cut by Darius Rucker in 2013 became a mainstream country smash. Today “Wagon Wheel” often causes both full-throated singalongs and groans, depending on whether or not you feel it’s been overplayed over the years. JS 

86. "L.A. Freeway" by Guy Clark (1975)

“If I could just get off of this L.A. Freeway without getting killed or caught...” Has there ever been a better open-ended, existential proposal given in a song than that? The analysis of “L.A. Freeway” deserves its own book, not just a few sentences. Is Guy Clark tired of the big-city life? Is he ready to chuck his musical dreams and return to Texas? Is he being optimistic or pessimistic? The song can be interpreted in such a wide variety of different ways. With mentions of his wife Susanna, “Skinny” Dennis Sanchez, and simpler times, Clark (as he always does) paints a vivid portrait and makes the listener think about every last detail. Oh, and the outro is one of the prettiest and most soothing pieces of music I can think of. NK

85. "Hungry Eyes" by Merle Haggard (1969)

Merle Haggard’s music is complex and simple at the same time. Complex because it explores the human condition in a deeply psychological manner. Simple because Haggard was able to write about the complicated state of humanity in such a relatable and authentic way. At its heart, “Hungry Eyes” is about growing up in deep, true poverty. And yet dig below the surface, and you find the love of a family and the strength it takes to hold everyone together. “Hungry Eyes,” along with “Mama Tried,” is the best example of The Hag’s ability to combine his own life with the classic writer’s poetic license to create a poignant, specific vignette. NK

84. "Friends in Low Places" by Garth Brooks

Garth Brooks’ “Friends in Low Places” has become the go-to country song for drunken karaoke nights and that could be a really good or bad thing depending on how you feel about that. The feel-good singalong about getting some comeuppance on an ex is one of those songs even non-country music fans will know and many will love. The song, co-written by Dewayne Blackwell and Earl Bud Lee, was made for Garth Brooks and helped to really make Garth Brooks. It’s a song that is just right for a larger than life figure. The song, released in 1990, became one of the biggest releases of the year and eventually of Brooks’ career winning Single of the Year at both the CMA and ACM Awards. JS

83. "The Pill" by Loretta Lynn (1975)

Despite its reputation as a backward-thinking genre of music, country music has largely been at the forefront of social issues throughout its history. Though while the birth control pill had been on the market for nearly a decade before this song was recorded, I don’t think anyone quite expected a song like this. Loretta Lynn had already turned heads by asserting her dominance in a male-dominated world of its time (quickly changing gears, of course) through other songs, but “The Pill” addresses a social issue in the only way Lynn knows how – by saying what’s on her mind, consequences be damned. Country music, for decades, has always been better because of it. ZK

82. "Murder on Music Row" by Alan Jackson & George Strait (2000)

Out of any song on this list, “Murder On Music Row” is the one that will inevitably make more than a few country fans smile as they pump their fist into the air. “Murder On Music Row” sways along at an easy tempo, but it resonates like an anthem. Originally recorded by the bluegrass group Larry Cordle & Lonesome Standard Time and written by front man Larry Cordle and Larry Shell, most are familiar with the Alan Jackson and George Strait version of the song. It’s the protest song to end all protest songs, pointing a fair criticism of the genre’s stray from its roots in a timeless fashion. Obviously, though, the industry must not have quite understood the message, as while it charted without being an official single and nabbed a CMA Song Of The Year distinction, it’s a message that resonates louder today than when it first debuted. ZK

81. "Killin' Time" by Clint Black (1989)

Few things in the history of country music have ever sounded better to my ears than the opening guitar licks of Clint Black’s “Killin’ Time.” The title track to Black’s 1989 debut album, co-written by Black and guitarist Hayden Nicholas, was one of a few tracks off the album that showed Black was a force to be reckoned with. The album, arguably the greatest debut in country music history, featured four straight No. 1 hits – but “Killin’ Time” featuring the tried and true country trope of drinking your lost love away is the most memorable. JS
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