9. Conway Twitty – “That’s My Job”
Conway Twitty was one of country music’s most commercially successful artists, but he is less often called one of its greatest singers. This song shows the error in such a judgment. Though not one of his dozens of #1 country hits, “That’s My Job” stands out as a tearjerker with few parallels in country music. Like multiple songs on this list, this song is an example of what scholar Nadine Hubbs calls the Three-Verse Life Cycle song, here paying tribute to a father’s nonchalant, matter-of-fact approach to parenting. The recording is made more emotionally affecting by Twitty’s exceptional performance.
8. Tim McGraw – “Live Like You Were Dying”
This anthem became an instant classic and a signature song of Tim McGraw’s three-decade run of hits, winning Single of the Year and Song of the Year at the CMAs. Probably the loudest-sounding production on this list, “Live Like You Were Dying”, boasts an uplifting message and has inspired many, including myself, to live in their truth, as I wrote about in this essay. Say what you want about mainstream country, but this is a masterpiece.
7. Townes Van Zandt – “Pancho and Lefty”
“Pancho and Lefty” is one of the greatest story songs ever written. Made most famous by Willie Nelson and Merle Haggard’s 1983 version, Townes Van Zandt’s song tells of bandits on the run until one is killed, with the other likely acting as the police informant. The best version of this song is on the solo acoustic album Live at the Old Quarter, Houston, Texas, released in 1977, with Van Zandt performing with just his voice and an acoustic guitar. The most gorgeous cover of this song belongs to Emmylou Harris, but like with other Van Zandt songs, “Pancho and Lefty” was best performed by the man himself.
6. Lefty Frizzell – “The Long Black Veil”
The spookiest record on this list features a story with murder, a ghost, gallows, and cheating, plus extra-spare acoustic backing, with quiet acoustic guitar strumming and brushed drums echoing Lefty Frizzell’s muted delivery. “The Long Black Veil” is in the tradition of older murder ballads like “Pretty Polly”, “Knoxville Girl”, and “Delia” (aka “Delia’s Gone”), but the story, the production, and Frizzell’s eerie performance make it more significant than any of them.
5. Bobbie Gentry – “Ode to Billie Joe”
Bobbie Gentry’s 1967 self-penned crossover smash hit, “Ode to Billie Joe”, is one of the most understated and least sentimental country hits ever. The song is a masterpiece of detail-oriented showing and not telling in storytelling, but Gentry’s propulsive acoustic guitar and moody vocals make this recording rich with unique atmosphere, as does the call-and-response string arrangement echoing the drama in the lyrics. The song is most remembered for its ambiguities–listeners will never know or stop speculating what Billie Joe and the narrator threw off the Tallahatchie Bridge–but the family’s indifference to Billie Joe’s suicide makes for an unusually chilling portrait.
4. Johnny Cash – “Folsom Prison Blues”
Few lyrics in country music are as iconic as, “I shot a man in Reno just to watch him die,” that one line about death defines the song, especially as Johnny Cash performed it in 1968 at the real Folsom Prison. Critic Hanif Abdurraqib wrote that the cheers following that line in that performance were overdubbed on record to make the song sound more chilling. Still, Cash’s song was always a standout, but here, his performance with his band is incendiary.
3. George Jones – “He Stopped Loving Her Today”
In any universe, this recording is a towering achievement. Many have called this the greatest country song ever, and the titanic performance of George Jones is a big reason why. In the verses, Jones is both restrained and soaring, as he insinuates and imbues lines like “Dated 1962” with enough emotion to suggest something is about to explode. When the chorus comes around and the orchestral arrangement swells, the song’s drama unfolds to a far greater degree. Despite the potentially cringy elements of humor and sentimentality–the dead man’s smile in the casket and the recitation near the end come to mind–this is one of the most moving records of all time. Though I do not put “He Stopped Loving Her Today” at #1 here, it is an incontestable masterpiece that deserves all the accolades it has received.
2. The Carter Family – “Can the Circle Be Unbroken (By and By)”
The quintessential theme song of country music, known as “Will the Circle Be Unbroken”, is adapted from a hymn and tells a sad story with redemptive strains of a possible reunion in the afterlife. The recording is spare with three voices and one guitar, played by the legendary Maybelle Carter. Today, this 1935 recording puts most country records to shame with its performance and sense of atmosphere. Sara Carter’s lead vocal sounds plaintive, but when she, Maybelle, and A. P. blend, the song soars with joy. This recording is among the very greatest in country music.
1. Kathy Mattea – “Where’ve You Been”
Before anyone attacks me for putting this at #1 ahead of “He Stopped Loving Her Today”, I must assert that this song is one of the most heartbreaking and well-written story songs I have ever heard. Achingly tender and sparsely arranged, “Where’ve You Been” is based on the true story of the love co-songwriter Jon Vezner’s grandparents had for each other. An immediate standout among Kathy Mattea’s 1980s and 1990s hits, the recording makes the already great song even more remarkable. I won’t spoil the story, but If you aren’t paying attention and miss its trajectory, you will miss one of the most genuinely moving and well-written songs ever recorded. To my ears, this is the ultimate tearjerker in country music.