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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.

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,