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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.

Shelby Lynne Saddest Country Songs

Shelby Lynne, “Heaven’s Only Days Down the Road”

Heavy doesn't even begin to describe Shelby Lynne's acoustic retelling of her own fractured home life in "Heaven's Only Days Down the Road." Off 2011's Revelation Road, the track turns the clock back to 1986, when Lynne was 17. It was then that her estranged alcoholic father shot and killed her mother before turning the gun on himself. The gripping murder ballad digs deep into her dad's psyche ("Load up the gun full of regret/I ain't even pulled the trigger yet") and eventually remarks that the two little girls — Lynne and younger sister/fellow country artist Allison Moorer — are better off this way. Two gunshots serve as final punctuation.

Alan Jackson Saddest Country Songs

Alan Jackson, “Where Were You (When the World Stopped Turning)”

Written after the terrorist attacks on September 11th, 2001, "Where Were You (When the World Stopped Turning)" stands as one of the most poignant "of the people" songs ever written. Jackson started the song as a way for him to make sense of what was happening in the wake of the attacks, and when the song was finished, he was reluctant to release it to the public — because of its very personal nature and because he didn't want anyone to think he was exploiting tragedy. Eventually, his family and friends at his record label persuaded him, and Jackson debuted "Where Were You (When the World Stopped Turning)" live at the 35th Annual CMA Awards that November, receiving an emotional standing ovation. Jackson's heartfelt expression of stunned helplessness encapsulated the American collective consciousness perfectly and the song stayed at the top of the charts for five weeks. However, its highest distinction lies in the fact that on November 16th, 2001, Georgia congressman Mac Collins, honored the song on the floor of the U.S. House Of Representatives, placing it in the permanent Congressional Record.

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)

GAB Archive/Redferns/Getty


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

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

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

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.

Johnny Cash saddest country songs

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."

John Michael Montgomery Saddest Country Songs

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.