My buddy Nick swears that “Chiseled in Stone” by Vern Gosdin is the saddest country song ever written. “You ran crying to the bedroom,” it begins:

I ran off to the bar
Another piece of Heaven gone to Hell
The words we spoke in anger just tore my world apart
And I sat there feeling sorry for myself

It’s a hell of start. Seldom has romantic strife been evoked so concisely. What words did they speak in anger? None, we suspect, that lovers haven’t always said. The point, I think, is that these lovers never dreamed they’d be the ones saying them. Nobody sets out to be miserable in love.

After a modest run as a singer and guitar player in California folk-country bands, Gosdin retired in the early seventies only to rally as a solo act later in the decade. Beginning in his mid-forties, he sent one song after another—“I’m Still Crazy,” “Is It Raining at Your House?,” “This Ain’t My First Rodeo”—into the top 10. “Chiseled in Stone,” which won the’89 CMA award for best song, helped him mount one of the greatest comebacks in country music. He was Music City’s patron saint of late bloomers.

Gosdin looked like a Burt. He had Bacharach eyes, Reynolds sideburns and mustache, Lancaster air. His pliant, world-worn voice took cues from George Jones, whose vocal performances of sentimental lyrics dredged out of wretchedness a pitiful joy. 

“Chiseled in Stone” harkens back to Jones’ signature hit, “He Stopped Loving Her Today.” In that song, Jones tells the story of a man who makes good on his promise to love the woman who broke his heart until the day he dies. Apart from Jones’ singular voice, which is its own steel guitar, what sets “He Stopped Loving Her” apart is the song’s narrative conceit. See, the story in question is recounted by one of the man’s friends. “You know,” he says in the final verse, as if pulling the listener aside and sharing a piece of privileged information, “she came to see him one last time,”

And we all wondered if she would
And it kept runnin’ through my mind,
“This time he’s over her for good”

The device enfolds the listener in the human drama. The move sort of turns the song into a simulacrum of country music. What country does best, “He Stopped Loving Her” suggests, is what this song is doing right now, namely converting a private and particular sadness into a shared and singable experience, one that provides no succor but the sad music of itself.

“Chiseled in Stone,” despite its grief-stricken tone, has something far more redemptive in mind. The contrition at the end of the first verse—“I sat there feeling sorry for myself”—injects a measure of expectancy, even hope, into the heartache invoked by the opening lines. The narrator was boiling when he fled the house, but now he’s cooled off. What, we wonder, has changed his mind? The second verse picks up the story. “Then,” Gosdin sings,

that old man sat down beside me and looked me in the eye,
And he said, “Son, I know what you’re going through”

There’s been an intervention. An old man, a widower, has heard the narrator venting to the barkeep, and has inserted himself into the conversation. His empathic overtures, gentle at first blush, amount to a jab before a left hook. “You don’t know about sadness till you’ve faced life half alone,” the old man continues, before delivering the line that gives the song its title: “You don’t know about lonely till it’s chiseled in stone.”

In response to the old man’s riff, the narrator has beaten a path back to his house, which, as it turns out, is where we’ve been all along, listening as he relays the fortuitous encounter to his partner. En route he has picked up a peace offering. “So,” he tells his lover, “I brought these pretty flowers hoping you would understand sometimes a man is such a fool,”

Those golden words of wisdom
From the heart of that old man
Showed me I ain’t nothin’ without you

I don’t know about saddest country song ever, but I think “Flowers” by Billy Yates could give “Chiseled in Stone” a run for the saddest song featuring a bouquet. The two songs, at least to my ear, are in conversation. It’s as if Yates, who performed “Chiseled in Stone” at Gosdin’s ’09 Grand Ole Opry tribute concert, suspected Gosdin’s ballad had anguish to spare.

“Flowers” never bagged any industry awards. It was released in’97, just as the neo-traditionalist movement ushered in by artists such as Gosdin and carried forward by Alan Jackson and Patty Loveless was ceding territory to the pop sensibilities of Tim McGraw and Shania Twain.

“Flowers” peaked at #36 on the Billboard country chart and then faded from country radio all together. Yates, who worked as a barber on Music Row before landing his first record deal, found greater success as a songwriter. Among others, he co-wrote “Choices,” the stunning recantation of honkytonk living for which George Jones won his final Grammy, in ’99.

Like “Choices” and “Chiseled in Stone,” “Flowers” is relayed from the perspective of a brokenhearted man. Here, however, Yates withholds the details of what his character has done, beginning instead with a litany of what he hasn’t. “I should’ve took you dancin’,” the song opens, “a little candlelight romancin’, with roses.” Offset by that comma, by a heavy pause in Yates’ delivery, the roses are key. They hang over the rest of the song even though they don’t appear again until the final line.

In the following verses, the reasons for the narrator’s romantic negligence come into view. “But I was high up on a barstool,” the song goes on, “I was such a blind fool, now I know it.” He was “high up” back then, but he’s humbler now.

You won’t believe how much I’ve changed since you left
It took losin’ you, for me to find myself

The changes are manifold. In the following verses, we learn the narrator has kicked the bottle and secured a steady job. He’s bought “a brand-new suit” to wear to church on Sundays. To hear him tell it, he’s a brand-new man. Our suspense grows—we wonder whether a partner walking out would in fact bring about a change of such magnitude; we wonder if he’s stretching the truth.

Where the song goes next you just don’t see coming. “I went by the junk-yard,” the narrator tells us. His car is there and yet the sight of the wreckage doesn’t bring back memories of a crash but rather of the scene that preceded it. “I still see you on your knees,” he says

Beggin’ me not to drive
But I took away the keys
And made you climb inside

What starts as a hackneyed meditation on heartache, one that seems like yet another rearranging of the tropes used in a thousand country songs, has been transfigured into a solitary graveside service. “Oh, I’d take your place,” the narrator concludes,

in this field of stone
If I only had the power
Look what it took
For me to finally bring you flowers

There’s a touch of gallows humor to that phrase “look what it took,” as if the man’s failure to buy flowers while his partner was living had been a running joke between them, as if all of the other changes wrought by her death pale in comparison to this one gesture, which is heartfelt and carefully calibrated, if, in the end, fruitless. Flowers, after all, don’t mean a thing to the dead.

The differing trajectories of “Chiseled in Stone” and “Flowers”—one regarded as a classic, the other hardly regarded at all—could be used to make the case, common among enthusiasts of traditional country music, that somewhere in the nineties the genre lost its way.

Country music, the line goes, stopped sounding sad and lonesome. It lost touch with its broken heart, started looking and sounding like the suburbs. Red wine replaced cheap whiskey. The night club drove out the corner bar. “The love of money and the search for worldwide fame slowly killed tradition,” George Strait and Alan Jackson sang in ’99 in “Murder on Music Row,” “and for that someone should hang.”

To be sure, there is some truth to this cynical characterization of the mainstreaming of country music. It’s telling that in the months before and after Yates released “Flowers,” Garth Brooks charted two number #1 songs, “Long-Neck Bottle” and “Two Piña Coladas,” a pair of boozy, breezy up-tempo anthems that sound something like the foil to Yates’ marvelous, if undoubtedly maudlin, tearjerker.

And yet for all their top-40 catchiness, the essential subject matter of Brooks’ songs—drinking, heartbreak, self-loathing—is undeviating. Perhaps the difference between Brooks and Yates, between nineties country and what came before, has to do, at least in part, with attitude. Instead of remorse, Brooks’ songs are fueled by a kind of giddy delusion, an approach that isn’t without precedent in the annals of classic country.

In Golden Age staples such as “Dang Me” and “In the Summer,” Roger Miller yowled about romantic frustration with an impromptu jauntiness that combined Jimmie Rodgers’s blue yodeling with Cab Calloway’s scat. Indeed Miller makes you wonder whether there ever was such a thing as traditional country music when country music, to hear him sing it, is so evidently a blender of musical styles.

What I mean to say is that in country music, as in every genre, sad songs take many forms. And if, on the one end, there’s the grandiose, nearly baroque sorrow of Gosdin or Yates and on the other the insouciance of Brooks or Miller, might there also be a place for the kind of entrenched sadness, situated just a hair shy of ambivalence, that finds expression in a song like Miranda Lambert’s “Dead Flowers,” a 21^st-century addition to the heartbreak canon?

Lambert’s records cover the emotional spectrum. Few singers do indignation and regret with more panache. With her whipsaw range, she is, more than any living country singer, the heir of George Jones. In “Dead Flowers,” however, rage and sorrow take a back seat to ennui. “I feel like the flowers in this vase,” Lambert deadpans over a forlornly propulsive electric guitar:

He just brought them home one day
“Ain’t they beautiful,” he said
They been here in the kitchen and the water’s turnin’ gray
They’re sittin’ in the vase but now they’re dead

Sad songs take many forms and the saddest songs are the ones about flowers.

Drew Bratcher was born in Nashville. He received his MFA from the University of Iowa. He lives in Chicagoland.