10. Hank Williams - "I’m So Lonesome I Could Cry"
If you’re looking for this song on the charts for Hank Williams, you would be mistaken. The song served as the B-side of “My Bucket’s Got A Hole In It,” a No. 4 hit in 1949. Still, the song made an impact with future generations. B.J. Thomas made it a pop hit in 1966, and artists such as George Jones, Gram Parsons and even Pittsburgh Steelers QB Terry Bradshaw recorded it, with the latter making it a Top-20 Country hit in 1976. And, if you had any doubt about this song’s inclusion on a list of sad country song, no less of an expert than Elvis Presley put those thoughts to rest, saying during his 1973 Aloha From Hawaii concert that “I'd like to sing a song that's ... probably the saddest song I've ever heard." So, that works for us!
9. Diamond Rio - "You’re Gone"
Paul Williams is typically recognized for some of the greatest copyrights of the pop music era, but the tunesmith -- also known for his acting work in the Smokey and The Bandit films -- also had success in the country market with this masterfully written composition that Diamond Rio made a hit in 1998. The song details a man who is enduring the break-up of a relationship, but also knows that he’s better for the experience. Diamond Rio’s Marty Roe delivered a standout performance, but Williams’s inspiration for the song -- penned with Jon Vezner -- was about the loss of a close friend. In 1998, he told Billboard’s Deborah Evans Price, “It just seemed like what we should write about are the people who are no longer in our lives who had a positive effect on us. And it just poured out of us. The people that pass through our lives -- we remember what they say to us, and we remember how they touch us.”
8. Porter Wagoner and Dolly Parton - "Jeannie’s Afraid Of The Dark"
The early works of Dolly Parton are filled with moments of Appalachian-tinged tragedy. Whether it be the eventual passing of “Gypsy, Joe, and Me” or the devastating sucker punch of “Me and Little Andy,” Parton has an uncanny knack for the sad country song. Quite possibly the top moment of this chapter of her illustrious career was this weeping ballad about a small child being afraid of the dark that served as the flip side of the 1969 top 10 hit, “We’ll Get Ahead Someday.” While the A-side was a No. 5 hit compared to this song’s No. 51 ranking as an album cut, in country music circles, you might be surprised which song has most effectively stood the test of time.
7. Merle Haggard - "Misery and Gin"
Country music has long had a reputation for “Cry In Your Beer” ballads about love lost. Merle Haggard’s 1980 nod to heartbreak remains one of his most essential moments, even though the record only made it to No. 3. The tune, from Clint Eastwood’s Bronco Billy film soundtrack, features Haggard in a bar with the beverage of his choice, lamenting a break-up he had just gone before. "Misery" never sounded more beautiful.
6. Red Foley - "Old Shep"
Many of the younger readers of this post about sad country songs might not know this early country music classic from Red Foley. But, if you have ever endured the pain of losing a pet -- either naturally or from having to put one down -- this song will grab you. Originally written in 1933, the song’s subject was a dog that the Foley family had as a child. According to the highly respected journalist Charles K. Wolfe in his book Kentucky Country, “Shep” was actually a German Shepherd named Hoover that wound up being poisoned by a neighbor. The song earned a place in pop culture as Elvis Presley sang it at his first public performance at age 10, and Led Zeppelin referenced the song in "Bron-Y-Aur Stomp,” a song about Plant’s dog.
5. Martina McBride - "Concrete Angel"
As far as modern country music is concerned, Martina McBride handles the four-minute sad country song about as well as anyone in the business. At the heart of that distinction is this 2002 release about a child who endures the torture of physical abuse at the hands of her mother before succumbing to her injuries. The Stephanie Bentley / Rob Crosby trademark was a sobering reminder that child abuse -- even in the modern era -- was still a major problem of social significance.
4. Rascal Flatts - "Why"
Though the No. 18 peak of this 2009 Rascal Flatts single was lower than any of their hits to that point, the message of this song was as emotional as anything the band had ever recorded. A song from the collective pens of Allen Shamblin and Rob Mathes, this gripping ballad about a man questioning why a close friend chose to end his own life touched an emotional chord with anyone who had ever gone through that experience. What you might not know about this selection on our list of saddest country songs is that the song was originally recorded by Faith Hill, but didn’t make her 2005 set Fireflies. Her version finally made an appearance on her 2016 Warner Bros. platter Deep Tracks.
3. Vern Gosdin - "Chiseled In Stone"
Nobody -- not even Jones, Haggard or Conway Twitty -- could exude pain and loss in a song in such a manner as Vern Gosdin. After all, that’s why he earned the moniker “The Voice.” The Alabama native had never really gotten the spotlight he deserved until he signed with Columbia in the fall of 1987 after recording for a series of independent labels. At the centerpiece of his debut album for the label, the singer chalked up perhaps his greatest moment with this composition -- penned with Max D. Barnes -- about the ultimate loss. At age 54, it was Gosdin’s time in the spotlight, earning a CMA Song of the Year trophy for his pain-drenched efforts.
2. Patty Loveless - "How Can I Help You Say Goodbye"
With growing up, we all go through a huge sense of loss. This wistful Patty Loveless performance from the pen of Karen Taylor-Good and Burton Banks Collins details two important moments in a woman’s life -- moving away from a friend at a young age and the end of a marriage, and how a mother’s love helped her to make it through the pain of the loss. However, the final verse -- about the eventual passing of her maternal influence -- knocks this one out of the tear-jerker ballpark, no doubt selling a lot of Kleenex boxes upon its release in the spring of 1994.
1. George Jones - "He Stopped Loving Her Today"
This 1980 George Jones evergreen routinely tops every list of this type -- almost to the point that you can get immune to the lyrics from Curly Putman and Bobby Braddock about a man who takes his love for his former flame to the grave. And, it’s been played so many times that would be easy, but try this. Listen to the song line by line with an open mind -- as if you never heard it before. Chances are pretty good that Jones’s timeless vocal will grab you even more than ever, but it’s impossible to discount the production of Billy Sherrill and the haunting funeral-like chorus notes of Millie Kirkham. It almost seems like a stock answer on lists such as these, but trust us, the song is just that damn good.