Country music was practically built on hard times and bad luck. Since its inception, a do-or-die attitude surrounding romance leaves many of our cowboys heartbroken and alone more often than they’d probably like to be. It’s a common theme that, when executed correctly, provides us with some harrowing accounts of what it’s like to walk a mile in their boots. In the spirit of Valentine’s Day, we’ve decided to collect and rank what might be the ten most chilling ballads on lost love and how our favorite artists respond to heartbreak.
The selection process was fairly abstract, so apologies beforehand if your favorite breakup got left off the list. We’re mostly looking for tracks that adhere to the theme of losing a loved one, willingly or unwillingly, and how artists and songwriters interpret that grief. This isn’t as much a ranking of the songs by objective quality as it is trying to see who checks most or all these (fairly undefined) boxes. While another artist or writer originally wrote some of these, we’re more looking at a performance that evokes the most emotion you could get out of a particular song. That being said, we’ll try to show some love to the original penmen or performers if we can.
The country is known for not pulling its punches, and these few knock the wind out of you from the first pluck of a guitar string.
10. Empty As A Drum – Turnpike Troubadours
We’ll start off with a little red-dirt rasp as Turnpike takes us to the back of the bar with high hopes and low self-esteem. A quaint arrangement coating Evan Felker’s matter-of-fact delivery is a great way to paint the picture of creaky floorboards and empty hearts the group is going for. He waits patiently for a girl to arrive after something goes wrong in the relationship. When she finally does, well, who knows? We end on a bit of a cliffhanger when she bursts through the front door and leaves the rest of the evening up to interpretation. While the ambiguity may spin some of this into the positive, that mystery and misery that’s apparent is enough to earn it the first spot on this long, dark, and winding list.
9. Cryin’ – Glen Campbell
Originally performed by Roy Orbison, the closer on 1967’s Gentle On My Mind is as delicate as the wind Campell seems to float with, sending shivers down your spine with his signature vocals and almost shocking falsetto. Here, Campbell imagines he’s over that lost love, only to have two of his five senses send him into a shock when he’s confronted with her presence. Its grand, almost orchestral arrangement swells, and swells and holds off on its climax for almost two minutes before bursting into life and before Campbell bursts into tears on the last refrain of the chorus. It’s a heart-wrenching rendition of a classic song and one that just screams with the theatrics that can come with misery.
8. Teardrop Inn – Sundy Best
It’d be remiss of us to have this list void of any cheating songs, infidelity, or adjacent storytelling. So, it’s essential to acknowledge that trope while paying homage to one of country music’s darkest corners and soul-bearing sounds.“Teardrop Inn” was originally released by Tommy Webb in 2009 (and based on an actual bar) but has since taken the Kentucky and West Virginia bluegrass circles by storm. Sundy Best, the brainchild of Nicholas Jamerson, encapsulates their warts-and-all mentality perfectly. It’s an ode to love in the Appalachian hills, the minor imperfections and major implications that come from a place called the “Teardrop Inn” and all those who inhabit it. It’s a haunting and hellish rendition of small-town love, and rather seeing your beau six feet under than with that skank from down the street. According to Tommy Webb, it’s an urban legend from Kermit, WV, that holds some truth to it. That might make it all the more dour.
7. Funny How Time Slips Away – Willie Nelson
In interviews, Willie Nelson stated that the title of this song came to him on a drive where he thought it was peculiar that no one had thought of the title before. Over 60 years later, it’s clear that while the Redheaded Stranger had solid gold in his hands, he also practically incited a new saying alongside his then-new hit. Before he was smokin’ and tokin’ down the highway, Nelson was making astute observations on the evasive qualities that time holds and displaying how gently it consumes us. You imagine he’s speaking to someone who was once his everything, now having trouble grasping that his former lover has let it consume her far more than he has. In the end, all he can do is sit back and laugh.
6. Whiskey and You – Chris Stapleton
It seems to be a recurring theme where some of the most dour moments come from the most insular tracks or stripped down on their respective records. Rather than hone in on the blues-infused jams Stapleton spends most of 2015’sTraveller dispensing, “Whiskey and You” hits the brakes virtually without warning. About halfway through the record, we ponder if drowning out your sorrows is such an unhealthy alternative to facing heartbreak cold turkey. “But one’s a liar that helps to hide me from my pain, and one’s the long gone bitter truth. That’s the difference between whiskey and you,” Stapleton croons behind stifled sobs. A whisper climbs into a wail under tactfully placed plucks and strums. It makes you wince with every breath—just unbelievably raw, minimalistic storytelling from one of the modern country’s most grandiose voices.
5. Caroline – Colter Wall (feat. Belle Plaine)
Colter Wall is maybe country music’s preeminent orator of the modern era. It’s especially evident in “Caroline” as he recounts the tale of a man whose wife is long gone and now taking residency amongst the clouds far out of his reach. His voice, leathery in its texture, is a perfect embodiment of that old man widow archetype he’s going for here, and he’s even smart enough to seek assistance with an uncommon feature from Belle Plaine. Her backing vocals throughout the track’s chorus help emulate that sense of being watched over by a loved one. He’s certain that their headstones in death like their hands were in life, will be clasped together for eternity. True endearment in the most depressing of senses.
4. Broken Window Serenade – Whiskey Myers
There’s a girl breaking your heart of her own sound mind, and then there’s a girl breaking your heart because of her unsound actions. Whiskey Myers practically owns the deed to the latter piece of that puzzle after his breakout hit in 2011. We’re in for a bumpy ride when that harmonica cries out its first few notes. In just under six minutes, we get a horrific retelling of falling in love with someone ill-fated and looking for fulfillment in all the wrong places. Patiently, our narrator waits for her to realize that he can at least provide her some comfort, only for her final resting place to be in a coffin rather than in his arms. It’s an incessantly traumatic track, never letting up on the recounting of our girl next door’s hard luck. Maybe it’s only a silver lining; she equally gets her flowers in life and death.
3. They’re Hanging Me Tonight – Marty Robbins
This one is tough because it cross-breeds between a heartache tune and a murder ballad. Still, Marty Robbins’s implications on practically every other track on this list make this an absolute necessity in structure and influence. The beats are pretty simple: our cowboy catches his lady with another man, he kills him, and now he’s facing justice. Robbins and his flighty, righteous baritone have a knack for painting him as the hero throughout his catalog, never really reaching a register that suggests malice or ill-intent, but that’s what makes this one so great. It’s downright evil, never really suggesting an interpretation of fate.
2. Whiskey Lullaby – Brad Paisley (feat. Alison Krauss)
We all knew it was coming. Brad Paisley’s standout slow-burn, “Whiskey Lullaby” grapples with some of the most intense themes in songwriting and handles them in a brutal yet delicate fashion. The dichotomy of those emotions over a haunting backdrop is amplified to eleven here with lines like “put a bottle to your head and pull the trigger.” Depression and alcoholism are commonplace in the great American songbook, but rarely are they utilized in such a smart and savvy fashion as they are here on one of modern music’s most gut-wrenching breakup ballads.
1. He Stopped Loving Her Today – George Jones
A good ole boy always keeps his word; nowhere is that better exemplified than at the top of our list. Not having had a #1 song in over half a decade, plenty began to write off George Jones as a has-been, and apparently, so did the soulmate of our protagonist on “He Stopped Loving Her Today.” After pledging his love to her for all eternity, the song’s subject lives his life vowed to one woman only, till death do him part, and eventually carrying that loyalty with him to the grave. It’s a blossoming track that builds and builds as our subject and our hearts continue to fall apart. Not only is it one of the most iconic Jones songs, but it’s also one of the greatest tragedies in the history of twang.
