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40 Saddest Country Songs of All Time

Cry, Cry, Cry: From George Jones to Brad Paisley, the biggest weepers ever

George Jones and Brad Paisley

George Jones (1976) and Brad Paisley (2014).

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Through the hillbilly music of the 1920s, the honky-tonk of the Forties and Fifties, the Bakersfield movement of the Sixties, bluegrass, Western swing, outlaw and contemporary pop, country songs still continue to break our hearts. Like no other musical genre, country stories of loss and heartbreak turn the old “tear in my beer” cliché into a sad, salty reality. So grab a few tissues and check out our list of the 40 saddest country songs ever written.

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Faron Young, “Hello Walls”

Honky-tonk star Faron Young was hanging at Tootsie's Orchid Lounge near the Grand Old Opry when a struggling tunesmith with a stack of rejected demos played him this song. The melody suggests lonesome isolation even if you don't understand a word of English. "Hello Walls" became a major crossover hit for Young, and established the career of that young writer, Willie Nelson.

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Johnny Cash, “Sunday Morning Coming Down”

From breakfast beer to dirty shirts, no song better describes the feeling of waking up hungover and alone than "Sunday Morning Coming Down." Kris Kristofferson wrote it from the depths of a condemned Music Row tenement soon after his wife had left and taken their daughter with her. "Sunday was the worst day of the week if you didn't have a family," Kristofferson told biographer John Morthland in 1991. "The bars were closed until 1 in the afternoon… so there was nothing to do all morning." Ray Stevens recorded "Sunday" first, but Cash's version — with all the pathos a phrase like "nothin' short of dyin' that's half as lonesome as the sound" deserves – was the one that made it to Number One. "Actually," Kristofferson told NPR last year, "it was the song that allowed me to quit working for a living."

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John Michael Montgomery, “The Little Girl”

A dysfunctional family's plight hits a disastrous final note in John Michael Montgomery's soap opera tale "The Little Girl." The last Billboard Hot Country Songs Number One of his career details a young girl hiding behind the couch while her drug-addled ma and alcoholic pa duke it out — with fatal results. Backed by harmonies from bluegrass stars Alison Krauss and Dan Tyminski and an arrangement to urge on the waterworks, Montgomery remains even-keeled as the fable reaches its spiritual conclusion.

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George Jones, “He Stopped Loving Her Today”

 Written by the same team behind ex-wife Tammy Wynette's 1968 signature "D-I-V-O-R-C-E," "He Stopped Loving Her Today" might be country music's greatest punchline song ever. In well-drawn detail, it describes a torch-carrying man whose love finally comes back to him — at his funeral. It's such a natural fit for the Possum's anguished voice, you can’t imagine anyone else singing it. And it almost didn’t happen.

In Bob Allen’s 1996 Jones biography The Life and Times of a Honky Tonk Legend, producer Billy Sherrill said that Jones "hated the melody and wouldn’t learn it" because it was "too long, too sad, too depressing." Even after he finally gave in, Jones groused that, "Nobody'll buy that morbid son of a bitch." Instead, “He Stopped Loving Her Today” became Jones' first chart-topper since 1974 and singlehandedly breathed new life into his career.

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Brad Paisley and Alison Krauss, “Whiskey Lullaby”

On record and especially onstage, Brad Paisley and Alison Krauss can both play the class clown to perfection, but this duet (off Paisley's 2003 Mud on the Tires) will exquisitely ruin your whole afternoon, a star-crossed lovers' lament in which both parties drink themselves to death, one verse at a time. Written by Bill Anderson and Jon Randall (the latter starting with the line "He put that bottle to his head/And pulled the trigger" and spiraling outward, and/or downward), it went Top Five country and took the ACM Award for Vocal Event of the Year. The video packs a Lifetime movie's worth of pathos into the first two minutes alone.

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Hank Williams, “I’m So Lonesome I Could Cry”

Not just one of country music's most evocatively ripe lyrics but maybe also its most acute diagnosis of clinical depression: Everything the singer encounters — from the weep of a robin to the whine of a train to the fact that a falling star makes no sound at all — mirrors his dark mood. Hank thought it was a poem, not a song, written initially for his alter ego "Luke the Drifter" to recite. Good thing he reconsidered: Without the gentle lope of the melody softening the mood, what Elvis introduced as "probably the saddest song I've ever heard" during his legendary 1973 televised concert in Hawaii might have been too hopeless to endure.

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Martina McBride, “Concrete Angel”

No one in country music has done more to bring attention to abuse than Martina McBride. Where her smash "Independence Day" (one of Rolling Stone's Greatest Country Songs of All Time) is about spousal abuse, McBride's 2002 track "Concrete Angel" details the abuse of a little girl at the hands of her mother: "She hides the bruises with linen and lace." Toward the end of the song the narrator describes "somebody [crying] in the middle of the night," while the neighbors try to ignore it. But does it at least have a happy ending? Well, while the song doesn't (the "concrete angel" in question is a grave marker), but its legacy does. "I've certainly had a lot of people tell me when I'm performing at shows what the song means to them," said co-writer Rob Crosby. "The fact that a few kids have seen the music video, which flashes the number for Child Help USA, and have been able to escape a bad situation is a gratifying thing."