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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.

Red Foley 'Saddest Songs'

UNSPECIFIED - circa 1960: (AUSTRALIA OUT) Photo of American musician Red Foley (1910-1968) posed with acoustic guitar circa 1960. (Photo by GAB Archive/Redferns)

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10

Red Foley, “Old Shep”

The rule about Chekhov's gun applies to dogs in country songs: If the pup appears in the first verse, it's going to be dead by the last. "Old Shep," a song written and originally recorded by Red Foley in 1931 (and performed by a 10-year-old Elvis Presley at the Mississippi-Alabama Fair in 1945), is based on a dog Foley had as a boy. As Shep gets older and his health wanes, the vet tells the boy that he needs to put the canine down. Even though the narrator picks up his gun, Old Yeller-style, he "just couldn't do it, I wanted to run/And I wished that they'd shoot me instead." Instead, Old Shep puts his head on the boy's knee and knowingly looks at him before peacefully passing away. In its final verse, Foley sings sweetly about Doggie Heaven, where "Old Shep has a wonderful home."

Lefty Frizzell Saddest Country Songs
9

Lefty Frizzell, “Long Black Veil”

Recorded during the dawn of the highly stylized Nashville Sound era, "Long Black Veil" was a musical departure for honky-tonk singer Lefty Frizzell. Amid a weeping slide guitar and soft, shuffling rhythms, Frizzell tells the tale of a man falsely accused of murder: Our hero can't provide an alibi — to do so would expose the affair he had been having with his best friend's wife — so he ends up executed for the crime, literally taking his secret to the grave. The saddest moment, however, is reserved for his lover, wailing under cover of the night winds. "Nobody knows but me," Frizzell sadly sings with his deep, gentle twang. "The Long Black Veil" was written by Danny Dill and Marijohn Wilkin, who say part of the inspiration for the song was based on a mysterious veiled woman who often visited the grave of Rudolph Valentino. 

Reba McEntire Saddest Country Songs
8

Reba McEntire, “She Thinks His Name Was John”

Like the somber second verse of TLC's "Waterfalls" ("Three letters took him to his final resting place"), this 12-hankie weeper from 1994 took on the AIDS/HIV crisis in no uncertain terms, with an errant one-night-stand spelling a young woman's doom: "She let a stranger kill her hopes and her dreams." Written by Steve Rosen and Sandy Knox (whose brother died of AIDS after a 1979 blood transfusion), the shattering ballad stalled out at Number 15 on Billboard's Hot Country Songs chart, but remains country music's highest-profile response to the crisis.

Faron Young Saddest Country Songs
7

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.