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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.

Saddest Country Songs

Ray Price, “For the Good Times”

Though Ray Price first met Kris Kristofferson when the latter was a janitor at Columbia Studios, the singer wouldn't remember the songwriter's name until he heard his "For the Good Times" demo between sets during an 1969 tour. After opening with the line "Don't be so sad," the song becomes increasingly tragic, detailing the last moments of a failing relationship before winding down to the closing chorus, "Hear the whisper of the raindrops blowing soft against the window/And make believe you love me one more time/For the good times." Price was immediately taken by these lyrics, but Columbia initially released his take on them as a B side for the honky-tonk "Grazin' in Greener Pastures." Nevertheless, by the end of 1970 "For the Good Times" had become the biggest country song of the year, and in the years following it would become a pop standard covered by artists like Elvis Presley, Frank Sinatra, Johnny Cash and Michael Jackson, who sang it for his mother at her 50th birthday party.

Saddest Country Songs

Vince Gill - Go Rest High On That Mountain


Vince Gill, “Go Rest High on That Mountain”

Though it sounds like an old standard, Vince Gill wrote "Go Rest High on That Mountain" in 1994, inspired by the death of country great Keith Whitley due to complications from alcoholism in 1989. Though Gill began writing the song after Whitley's death, he finished it following the death of his own older brother in 1993. Despite the devastating lyrical content and tragic circumstances, it's noted for its spiritually optimistic note. Plenty of others thought so too, as the song won two Grammys that year and received the BMI award for "Most Performed Song" in 1997.

Willie Nelson Saddest Country Songs

Willie Nelson, “Blue Eyes Crying in the Rain”

For years, Nelson had been writing hits for everybody from Patsy Cline to Frank Sinatra. But it took a cover to break him through as a singer in his own right — "Blue Eyes Crying in the Rain," written by Fred Rose in 1945 and recorded by Roy Acuff, Hank Williams, Conway Twitty and many others. Nelson's version might be the sparest of them all: just guitar, accordion and wounded warble painting an unbearably sad last-goodbye scene in vivid sepia tones.

"Blue Eyes" was centerpiece to Nelson's 1975 magnum opus Red Headed Stranger (a concept album about a cuckold turned murderous fugitive), and it didn't take long for Nelson's version to top the charts and become the definitive rendition. Even the Reivers and UB40 have recorded "Blue Eyes" since, and legend holds that it was the last song Elvis Presley ever played on his piano in Graceland before his 1977 death.

Dixie Chicks Saddest Country Songs

Dixie Chicks, “Travelin’ Soldier”

Austin-based singer-songwriter Bruce Robison was inspired to write "Travelin' Soldier" after a friend was activated for duty in the first Iraq war. Robison released the initial version of the song — the tragic love story of two lonely teenagers whose budding romance is trampled under the weight of the Vietnam War — in the mid-Nineties, but it became a chart-topping hit in 2003 after the Dixie Chicks re-recorded it when it again became relevant. The song peaks on a Friday night at the football game, when the young man's name is read over the loudspeaker as the crowd is asked to pray for the "list of local Vietnam dead." We find our young waitress "crying all alone under the stands," and it's clear that she's crying not only for her lost love, but for her dashed hopes of "never more to be alone, when the letter said, the soldier's coming home." Shortly after it topped the charts, controversy erupted when Natalie Maines said she was ashamed President Bush was from their home state of Texas. In the two weeks following, "Travelin' Soldier" dropped to Number Three, then off the charts completely.

Merle Haggard Saddest Country Songs

Merle Haggard, “If We Make It Through December”

Released in October 1973, "If We Make It Through December" tells the tale of a factory worker who gets laid off shortly before the holidays and then becomes wracked with guilt over his inability to buy his daughter some "Christmas cheer." With unemployment and inflation at a record high in 1973, and both oil and steel in short supply, America was in the middle of one of its worst recessions to date. But while headlines screamed of "bear markets" and "economic indexes," Haggard's song got right to the heart of the issue: the people behind those headlines. More importantly, it mirrored the optimism that shone through the struggles: "If we make it through December, we'll be fine." All of this gave the song — which hit Number One on the country charts that December — a shelf-life that lasted well beyond the holidays.

saddest country songs

Lee Brice, “I Drive Your Truck”

At the dawn of the 21st century, country ballads are indistinguishable from power ballads, give or take some small-town signifiers — in this case, the Braves hat, the field, the truck, the attention to gas mileage. Inspired by the story of a father who kept his son's Dodge around after the son was killed in Afghanistan, "Truck" isn't just an exploration of the ways we try and maintain connection to people we've lost through what they left behind, but about men: how they're allowed to feel, how they aren't. "You'd probably punch my arm right now if you saw this tear rollin' down on my face," Brice sings. "Hey, man I'm tryin' to be tough." Given the chance to visit his son's grave, the father quietly opts out. The song is there to emote in ways he feels like he can't.

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)

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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.