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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).

Getty Images

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 Sovine, "Teddy Bear"

Red Sovine, "Teddy Bear"

27

Red Sovine, “Teddy Bear”

In Red Sovine's best song, "Phantom 309," an out-of-luck traveler encounters the supernatural when he hitches a ride from a mysterious trucker named Big Joe. In his saddest, "Teddy Bear," a different trucker has some CB radio talk with a lonely boy who is "crippled and can't walk." Eventually, he gives the boy a ride in his rig, the boy's mom calls to thank him and Sovine himself sniffles the song to a close: "I'll sign off now, before I start to cry/May God ride with ya', 10-4 goodbye." "My ol' friend Teddy Bear" would later reappear in the singer's "Little Joe" — about a faithful dog who helps the same narrator get around after a thunder-storm crash somehow leaves him blind.

Dwight Yoakam Saddest Country Songs
26

Dwight Yoakam, “I Sang Dixie”

Even though he broke through as a West Coast cowpunk, the Kentucky-born Yoakam remains a Southern boy through and through. With its keening fiddle and general morbidity, "I Sang Dixie" is as forlorn as a Civil War lament, recounting a vagrant's sad and lonely death on a "damned old L.A. street" before concluding, "No more pain, and now he's safe back home in Dixie." It's one of several homesick songs Yoakam wrote after inspirational visits back home, and it was in his repertoire for nearly a decade before he released it. Pete Anderson, Yoakam’s producer-guitarist collaborator, regarded it as a hole card. “I thought it was his best song… a Number One record,” Anderson said in Don McCleese’s 2012 Yoakam biography A Thousand Miles From Nowhere. He was right. Released as a single off 1988's dark Buenos Noches From a Lonely Room, "Dixie" became Yoakam’s second Number One hit.

Doug Supernaw Saddest Country Songs
25

Doug Supernaw, “I Don’t Call Him Daddy”

"I Don't Call Him Daddy" tells the tale of a divorced couple and the young son caught in between them. In Dad's absence, Mama's new live-in boyfriend "takes care of things" — but despite this, the little boy refuses to call this new man, "Daddy," loyally assuring, "he can never be like you." Written by Reed Nielsen, "I Don't Call Him Daddy" was first recorded by Kenny Rogers, who released it as a single in 1987. The song never cracked the country Top 40 for Rogers, but Supernaw's version stayed at Number One for two weeks in December 1993. In a sad real-life twist, Supernaw has been cited for failure to pay child support.

Ray Charles and Willie Nelson Saddest Country Songs
24

Ray Charles & Willie Nelson, “Seven Spanish Angels”

When Ray Charles' career reached its late-Seventies nadir, the then 50-year-old singer found that Nashville, of all places, hadn't forgotten about him: Clint Eastwood duet "Beers to You" reached the country Top 50, a Loretta Lynn Opry gig was a rowdy hit and his fall 1980 Hee Haw appearance was so successful that Buck Owens joked, "You keep hangin' around here, and you'll get on steady." As it turned out, that's exactly what happened. In 1983 and '84, Charles recorded his first two country albums since the second Modern Sounds, and in March of 1985 Willie Nelson duet "Seven Spanish Angels" gave him his first Number One since 1966. A Marty Robbins-esque gunfighter ballad, the song tells the story of a pair of Mexican bandits who lose their life to a posse of bounty hunters attempting to bring them back to Texas. After the dude gets shot in his attempt to escape, the lady points his empty gun at his attackers, ensuring that she will suffer the same fate.

Rascal Flatts Saddest Country Songs
23

Rascal Flatts, “Skin (Sara Beth)”

Rascal Flatts tackle an affliction that hurts even more than "What Hurts the Most" with "Skin (Sara Beth)." For a Kentucky teenager, the transformative challenges of cancer and chemotherapy fly in the face of normalcy on this ballad (originally a hidden track on 2005’s Feels Like Today) that reached Number Two on the Billboard Hot Country Songs chart. Strings, piano, light pedal steel, and a stoic Gary LeVox flesh out how she’s "scared to death" of an upcoming prom she must face with no hair. Wisely, her date assuages trepidation by showing up with his dome shaved to bring this emotional scene to a close.

Lucinda Wiliams Saddest Country Songs
22

Lucinda Williams, “Sweet Old World”

Written in tribute to a friend who committed suicide, "Sweet Old World" is a standout from Williams' 1992 album of the same name, which is full of contemplations about life, death and all that we leave behind. Williams began writing the song in 1979 after poet Frank Stanford killed himself with three gunshots to the heart, but it didn't see the light of day until more than 13 years later. Williams told the New Yorker she held the ballad "because my career has been distinguished by other people, who have always been men, telling me what I should sound like." Sonically, it's rather simple, with Williams singing into an empty abyss, bursting with both sadness and anger.

Vern Gosdin Saddest Country Songs
21

Vern Gosdin, “Chiseled in Stone”

Within the weepy "Chiseled in Stone," the boundlessly forlorn Vern "The Voice" Gosdin goes straight for the heartstrings and yanks. Tinged with gospel harmony and a tad overstuffed production-wise, the 1989 Country Music Association Song of the Year details the aftermath of a lovers' quarrel, a.k.a. "another piece of heaven gone to hell." While Junior drinks his sorrows away, an elderly figure reminds him that he could have it a lot worse: "You don't know about sadness, 'til you face life alone/You don't know about lonely 'til it's chiseled in stone." In other words, buck up and figure it out — at least she's not dead.

Saddest Country Songs

UNITED KINGDOM - JULY 05: O2 ARENA Photo of Dolly PARTON, Dolly Parton performing on stage (Photo by Harry Scott/Redferns)

Harry Scott/Redferns

20

Dolly Parton, “I Will Forever Hate Roses”

The red rose is our culture's most enduring symbol of romance — which is just a nice way of saying it's the hackiest, most overused love cliché there is. But Dolly uncovers a new wrinkle in a shopworn image. Here, her man sends her the flowers, along with a curt goodbye note when he dumps her, leading her to discover, as another poet once sang, that every rose has its thorn, just like every cowboy sings a sad, sad song.

Saddest Country Songs
19

Mel Tillis, “Life Turned Her That Way”

Songwriting great Harlan Howard — the man who defined country music as "three chords and the truth" — masterfully straddles the line "sympathetic" and "kind of patronizing" in this sharp appraisal of how a history of heartbreak left a woman "cold and bitter." Little Jimmy Dickens recorded it first. Ricky Shelton had a Number One hit with it. But Tillis' cool reserve in his 1967 version, echoed in a stately piano accompaniment, mined the lyric for maximum devastation.

Saddest Country Songs
18

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

17

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
16

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
15

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
14

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
13

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
12

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
11

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

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.