So Lonesome I Could Cry: Twelve of the Saddest Classic Country Love Songs

Lovesick blues.

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14 February 2015, 8:46pm

Photo courtesy of George Jones' Facebook

In a perfect world, we'd celebrate our love for our partners to the fullest every day of the year. There would also be no war, no sickness, no suffering, and free pizza every Friday. As it is, we've got ISIS, measles, and Valentine's Day. Bummer.

We've posted a lot of sexy music, fuckin' music, and cutesy music today, but for my last post of the day, I thought I'd redirect Cupid's arrow and go out on a low note. Really, it'd be easier to just list Hank Williams and George Jones' entire collected discography and leave it at that, but in the spirit of fairness, I've rounded up a few other lovelorn crooners to make extra sure that your Valentine's Day is as miserable as possible. There are plenty of modern hits that are more than capable of ruining your evening—from Dixie Chicks' "Travelin' Soldier" to Brad Paisley and Alison Krauss' weepy "Whiskey Lullaby"—but when it comes to lonesome, lovesick blues, you really can't go wrong with the classics.

Whether it's a woman, a man, or the bottom of a bottle of whiskey that done 'em wrong, the following tunes will make you wonder if it's worth getting out of February 14th alive.


"Cold, Cold Heart" - Hank Williams

Country music's eternal lonesome cowboy penned more than a few tearjerkers during his brief spell on this earth, but this one always rings especially blue. If you're going crazy loving someone who don't love you back, ol' Hank's got you covered.


"He Stopped Loving Her Today" - George Jones

The Possum lived hard and loved harder, and the bad times came out in his music. He really is the king of the sad country song, and his immortal tune boasts a surprise kicker that hits you like a ton of tear-stained bricks.


"D.I.V.O.R.C.E." - Tammy Wynette



Tammy's best known for her inadvertently feminist-baiting hit "Stand by Your Man," but her rendition of "D.I.V.O.R.C.E" is a far better repreentation of the darkness that haunted the soul of country's tragic one-time queen. Their dueling moans on "Golden Ring" may have summed up her doomed marriage to George Jones better than she or he could've ever predicted, but this one's all Tammy. Dolly Parton's version is more than worth a listen, too.


"Miss Being Mrs." - Loretta Lynn

The most famous coal miner's daughter to have ever come up out of Butcher Holler has had no shortage of hard times and written more than a few sad songs, but this widow's lament from her most recent album, Van Lear Rose, is absolutely devastating.


"Hello, Darlin'" - Conway Twitty

Conway belted out albums worth of love songs with Loretta Lynn, but he's a great talent in his own right; just witness how this desperate plea will stomp all over your heart quicker than you can say "Mississippi Woman."


"I Fall to Pieces" - Patsy Cline

Weeping strings, heartstring-tugging lyrics, and good lord, that VOICE...It's no wonder Patsy's such a legend. "You walk by and I fall to pieces..."


"She's Actin' Single (I'm Drinkin' Doubles)" - Gary Stewart

This one's got it all: a clever title, a cheating woman, a heartbroken man, and streams of whiskey. Knowing how Gary eventually met his Maker gives it an extra edge of pathos, though—in 2003, less than a month after his wife of 42 years' death, he was found dead of a self-inflicted gunshot wound to the neck.


“You Never Even Called Me By My Name“ - David Allan Coe

DAC isn't known for showing his soft side—he'd rather court controversey and romanticize bar fights—but this semi-parody ends up having a brutal effect on anyone who's ever felt love's sting.

"Amanda" - Don Williams

The Gentle Giant was so stranger to sadness, but one of his biggest hits, "Amanda," offered equal measures of sweetness and sorrow—standing behind his dreams while grieving over the life he wasn't able to give his lady.


"The Long Black Veil" - Lefty Frizzell

True love never dies—even if it ends in infidelity and murder—in this ghostly tune from a true Texas legend.


"Jolene" - Dolly Parton

Everything that Dolly touches turns to solid gold anyway, but this enduring classic cuts to the quick. Its urgent pace and Dolly's impassioned, pleading wail are impossible to ignore, and we've all watched as some would-be Jolene (or Joel) did their damndest to steal our loved one away.


"Give My Love to Rose" - Johnny Cash

God, this one HURTS.

"Give my love to Rose, please won't you mister
Take her all my money, tell her to buy some pretty clothes
Tell my boy his daddy's so proud of him
And don't forget to give my love to Rose..."

Kim Kelly is riding the lost highway on Twitter - @grimkim