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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.

Patsy Cline

Patsy Cline


Patsy Cline, “I Fall to Pieces”

Songwriters Hank Cochran and Harlan Howard were sure their new "I Fall to Pieces" would be a hit, but before it reached Patsy Cline, singers Brenda Lee ("too country") and Roy Drusky ("too feminine") both passed. But when the latter left the studio, however, Cline made sure that it wouldn't reach anyone else. "Drusky, that's a hit song you just let go," she remarked, "and I'm gonna get Owen [Bradley, Decca producer] to let me have it." That's how Drusky tells it, at least. According to Howard's wife Jan, Cline hated the song and refused to record it. Either way, "I Fall to Pieces" was put to tape in late 1960 and became the biggest country single of the following year. While the song's restrained honky-tonk beat emanates composure, Cline tries her best to do the same, keeping herself together in the presence of an old love wants her to be just his friend.

Saddest Country Songs

Alan Jackson, “Monday Morning Church”

Lyricist Brent Baxter's mother was an English teacher who used the phrase "as empty as a Monday morning church" to explain poetry to her students. Over a simple yet classic Erin Enderlin melody, Baxter applied that metaphor to the heart of an inconsolate widower enraged with God. The song was considered by Lee Ann Womack and Terri Clark before finding its ideal interpreter in the melodrama-averse Alan Jackson, whose quietly desperate performance suggests that Patty Loveless' backing vocal is all that stands between him and the abyss.

George Jones Saddest Country Songs

George Jones, “The Grand Tour”

Deciding which of Jones' sad songs is sadder than the next is like trying to decide whether coal is blacker than the bottom of the ocean or midnight on a moonless night. A husband's walkthrough of his empty house fresh after his wife has left for good, "The Grand Tour" marks the moment when Jones found synergy with Epic Records producer Billy Sherrill, whose downtown violins were initially seen as antithetical to Jones' honky-tonk roots but ultimately functioned as the castle that isolates the king from the world. Typically, the song is read as a story about Jones' painful divorce from fellow country star Tammy Wynette, finalized the year the song came out. One of its co-writers? George Richey, who married Wynette a few years later.

Saddest Country Songs

Pirates of the Mississippi, “Feed Jake”

At the heart of this song by early Nineties crew Pirates of the Mississippi is the stirring image of a man kneeling down to deliver the "Now I Lay Me Down to Sleep" bedtime prayer — pleading someone care for his best friend, a dog named Jake, if his owner should die before he wakes. However, "Feed Jake" is much deeper than the ballad of an orphaned pet. Remarkably progressive for a circa-1991 country song, "Jake" champions the rights of the homeless and lends support to the gay community: "Now, if you get an ear pierced, some will call you gay/But if you drive a pick-up, they'll say, 'No, you must be straight'/What we are and what we ain't, what we can and what we can't/Does it really matter?" 

Martina McBride Saddest Country Songs

Martina McBride, “God’s Will”

A classic in country music's ever-flourishing You-Think-You've-Got-Problems subgenre, "God's Will," the slow-burning piano ballad and emotional capstone to McBride's 2003 album Martina, valorizes a young boy with braces on his legs and a permanent, resilient smile on his face. Written by Barry Dean and Tom Douglas (and inspired by Dean's daughter), its lyrics dole out one Forrest Gump-channeling, Pinterest-worthy heart-suplex after another: "'Hey Jude' was his favorite song/At dinner he'd ask to pray/And then he'd pray for everybody in the world but him." 

Saddest Country Songs

UNSPECIFIED - JANUARY 01: Photo of Charley PRIDE; Country singer Charley Pride performing on stage, (Photo by David Redfern/Redferns)

David Redferns/Redferns


Charley Pride, “Where Do I Put Her Memory”

This Jim Weatherley-penned Charley Pride track never specifically says what happened to the woman whose memory can't be put away, but the way Pride sings it, it's safe to assume she's probably dead. The song, which became his 21st Number One on the Country chart when it came out in 1979, walks through all the things the narrator hid of his lost love. Gifts she gave him, the pillow she slept on and her drawers of clothes are all par for the course, but the lyrics get particularly sob-worthy with the devastatingly realistic mention of picking up "her hairpins and curlers/That she dropped on her side of the bed."

Gene Autry Saddest Country Songs

Gene Autry, “That Silver-Haired Daddy of Mine”

The Singing Cowboy's 1931 breakout hit and lifelong calling card — co-written with Jimmy Long at a railroad depot, and a gentle, pre-eulogistic apology to Dear Old Dad for slowly worrying him half into the grave — was the first Gold record ever, which hopefully was some consolation. A robust 80-plus years later, everyone from Simon & Garfunkel (sweet, delicate) to Jim Reeves (booming, authoritative) to Johnny Cash (reverent, quavering) to the Everly Brothers (intricate, definitive) to Sesame Street (furry, blue) to Billie Joe Armstrong and Norah Jones (um, hmm) has taken a shot at it.

Saddest Country Songs

Brooks & Dunn, “Believe”

A lithe, soulful, organ-driven eulogy slinking amid the duo's otherwise semi-raucous 2005 LP Hillbilly Deluxe, "Believe" tells the morbidly uplifting tale of "Old Man Wrigley" (no connection to the Chicago Cubs, which would be sadder), a neighborhood widower patiently waiting for the day he'll rejoin his wife and son in the hereafter. After drawing it up with superstar songwriter Craig Wiseman, Ronnie Dunn just absolutely sang the hell out of it, darting ahead of the beat and belting with a preacher's conviction. It just snuck into the country Top 10, but higher honors awaited it: "Believe" took the 2006 CMA for Song of the Year.

Merle Haggard 'Saddest Country Songs'

Merle Haggard, “Sing Me Back Home”

There's a toughness to Merle's sentimentality in this 1967 song befitting its real-life source material. It's a eulogy to fellow San Quentin inmate "Rabbit" Hendricks, who killed a police officer during a botched escape attempt and was sent to the gas chamber. We can only wonder what last song was sad and sweet enough for the death row prisoner to request his "guitar-playing friend" to peform.

Towns Van Zandt Saddest Country Songs

Townes Van Zandt, “Waiting Around to Die”

"This is the first serious song I ever wrote," Van Zandt told the audience before introducing this somber tune on his 1973 record Live at the Old Quarter. Originally released on 1968's For the Sake of the Song, it's the solemn story of a boozy rambler struggling to see the point of a fruitless existence that precedes eternal silence, ending with this tragic couplet: "His name's Codeine, he's the nicest thing I've seen/Together we're going to wait around and die." It's delicately heartbreaking and eerily prophetic to Van Zandt's early demise at 52 from alcoholism. Still, he was hesitant to play it at concerts since, as he said, "Nobody wants to hear blues on blues on blues." Turns out, they sure do. "That's what music's all about, when you hear something and you don't really have a choice," said Alex Turner of Arctic Monkeys of Van Zandt's work, "but to think, 'Oh fuck, all right, I'm going there.'"

Mary Gauthier - Mercy Now Saddest Country Songs

Mary Gauthier, “Mercy Now”

Mary Gauthier didn't begin her career until the age of 35, after struggling through alcoholism and drug addiction. But she certainly made up for lost time, with her 2005 major label debut, Mercy Now, proving a unique gift for stellar storytelling and composing characters that speak subtly to the human condition. On the title track, Gauthier seeks forgiveness and compassion from the micro to the macro level, using an unfolding lyrical device inspired by a similar mechanism on Lucinda Williams' "I Changed the Locks." "I honestly didn't even know if it was a good song or not after I finished it," she has said.  "I played it for my publisher and it was received with a yawn, and I think that threw me off. Once people started responding to it, I realized I might need a new publisher."

Tim McGraw Saddest Country Songs

Tim McGraw, “If You’re Reading This”

Inspired by a magazine article on war casualties, Tim McGraw and Brad and Brett Warren wrote "If You're Reading This" in the spring of 2007. The song's lyrics are in the form of a letter a soldier has written in case he dies in combat, with personal goodbyes to his mother, father and wife. McGraw performed the song for the first time at the ACM Awards in May 2007, and was joined onstage by military families who lost loved ones while in service to their country. Radio stations begin playing what was essentially a bootlegged version, which gained momentum with each passing week until the singer's label issued an official release.

Steve Wariner Saddest Country Songs

NASHVILLE, TN - OCTOBER 10: Painter/Singer/Songwriter Steve Wariner presents Wariner's Watercolors during the Three Part Harmony preview & private reception featuring Steve Wariner, celebrity portraits from photographer Russ Harrington, and dulcimers from the collection of the late dulcimer performer David Schnaufer at the Tennessee State Museum on October 10, 2013 in Nashville, Tennessee. (Photo by Rick Diamond/Getty Images)

Rick Diamond/Getty Image


Steve Wariner, “Holes in the Floor of Heaven”

In Steve Wariner's touching tale of loss, mourning and faith, the protagonist endures both the death of his grandmother and his young wife — who dies tragically after giving birth to their daughter. To cope with those losses, he's told that whenever it rains, it means there are "holes in the floor of heaven and her tears are pouring down. That's how you know she's watching, wishing she could be here now." In an extra twist, the song closes on their daughter's rainy wedding day. Thankfully, the lyrics didn't exactly mirror Wariner's real life. "I had just lost my grandmother not long before that," Wariner told CMT. "Billy [Kirsch, co-songwriter] and I were both drawing on the perspective of our grandparents for the first verse. And then just kind of used our creative liberty to paint the picture."

Red Sovine, "Teddy Bear"

Red Sovine, "Teddy Bear"


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

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

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

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

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.