25 Saddest Country Songs
Dolly Parton
Every genre of music has its sad songs, but no genre does sad songs like country music. There are songs about breakups, of course, but there are also heartbreakers about the devastation of coal mining, fighting off a posse, child abuse, abortion and every other devastating topic you can name.
Even Dolly Parton, purveyor of joy and sequins, has written plenty of songs that can only be listened to with a glass of whiskey in hand. “I used to write a lot of sad ass songs,” she said on the “Dolly Parton’s America” podcast in 2019. “You gotta remember too, that's how I grew up.”
One of her most emotional songs, “Daddy Come and Get Me,” is about a woman trapped in a mental institution at the behest of her husband. Parton based the song on her real-life aunt, whose husband put her away after she had a nervous breakdown. “I grew up with that,” Parton said. “And I was very impressionable.”
While that song is a sad one, it’s not one of the two Parton tunes to make this list (the first would be another, far more famous song made doubly sad by its association with the late Whitney Houston). Keep reading for more sad country songs to listen to when you need a good cry.
Related: Dolly Parton Shares the Heartwarming Stories Behind 10 of Her Favorite Songs
25 sad country songs
1. “I Will Always Love You,” Dolly Parton
It remains a hilarious irony that people use this song at weddings given that it is quite literally about saying goodbye to someone. Dolly Parton wrote it about her professional breakup with Porter Wagoner, but it’s versatile enough to apply in all kinds of heartbreaking situations.
2. “You’ll Never Leave Harlan Alive,” Patty Loveless
Written by Darrell Scott, “You’ll Never Leave Harlan Alive” has been covered by many, but Patty Loveless’ version—and her 2022 CMA Awards performance with Chris Stapleton—remains definitive. The six-minute ballad is about the devastation caused by coal mining in Harlan, Kentucky, and was inspired by a real gravestone Scott saw in the area that read, “You’ll never leave Harlan alive.” Loveless, whose father was a coal miner who died of black lung disease, was born in nearby Pikeville and imbues the song with a devastation that can’t be faked.
3. “Long Black Veil,” Lefty Frizzell
Lefty Frizzell originally recorded this classic tale of love and death (written by Danny Dill and Marijohn Wilkin) in 1959, but it’s been memorably covered by many artists, including Johnny Cash. His daughter Rosanne Cash released her own beautiful take, featuring Wilco’s Jeff Tweedy, in 2009.
4. “He Stopped Loving Her Today,” George Jones
A man vows to never stop loving a woman after she leaves him—and he doesn’t, until he dies: “He stopped loving her today / They placed a wreath upon his door / And soon they'll carry him away.”
5. “She Thinks His Name Was John,” Reba McEntire
Recorded by Reba McEntire in 1994, “She Thinks His Name Was John” is about a woman dying of AIDS after a one-night stand with a man who may have been named John. Cowriter Sandy Knox was inspired to write the song after losing her brother to the disease. “My brother was 29 years old when he passed away, and I put myself in his position if I had gotten that news,” Knox told CMT in 2004. “I wrote it from the standpoint of all the things that he was going to be missing—having a child, getting married, all of those things.”
6. “Where Do I Put Her Memory,” Charley Pride
This 1979 song is a pretty standard breakup tune about being haunted by the memory of a former lover, but Charley Pride gives the song a deeply spiritual touch with help from a gospel choir.
7. “Seven Spanish Angels,” Willie Nelson and Ray Charles
Only in country music can you find a ballad about an outlaw and his lover trying to outrun a posse who then share a romantic embrace before dying in a gunfight. The Willie Nelson and Ray Charles version is iconic, but Sierra Ferrell’s 2023 cover is gorgeous as well.
Related: Willie Nelson Reflects on Turning 90 and Why He Loves Being 'On the Road Again'
8. “Go Rest High on That Mountain,” Vince Gill
Vince Gill began work on this tearjerker following the death of country singer Keith Whitley, who died of alcohol poisoning in 1989 at age 34, and finished the song years later after his own brother died of a heart attack. The final result—featuring backing vocals from Ricky Skaggs and Patty Loveless—is nearly impossible to listen to without shedding a tear.
9. “Travelin’ Soldier,” The Chicks
The Chicks earned a reputation for hating America because they opposed the Iraq War, yet they’re responsible for one of the early aughts’ most devastating songs about the local ramifications of seemingly distant military action. While the song was written by Bruce Robison, The Chicks’ version was the first one released as a single—and it became a hit, despite its shattering subject matter.
10. “Sunday Mornin’ Comin’ Down,” Kris Kristofferson
Johnny Cash made this song a No. 1 hit, but it was written by fellow Highwayman Kris Kristofferson, who knew a thing or two about being down and out—he worked as a janitor at Columbia Records before his career as a songwriter took off.
11. “If We Were Vampires,” Jason Isbell
Jason Isbell’s “If We Were Vampires,” featuring harmonies from his wife, Amanda Shires, is about coming to terms with the fact that nothing lasts forever, even a love story between two soulmates. Sample lyric: “Maybe we'll get 40 years together / But one day I'll be gone / Or one day you'll be gone.”
12. “She’s Got You,” Patsy Cline
Patsy Cline’s version of this tune about a woman missing an ex who’s moved on can’t be beat, but plenty of covers will tear your heart in two as well: Cat Power did a version for her 2008 album, Jukebox, and Cline’s friend Loretta Lynn recorded her own take for 1977’s I Remember Patsy.
13. “Apartment #9,” Tammy Wynette
Tammy Wynette’s discography is full of tearjerkers, but nothing stings as much as “Apartment #9,” the tale of a woman sitting quietly in her apartment hoping her lover will come back after leaving her. Spoiler alert: he won’t.
14. “The Dance,” Garth Brooks
This song is basically the country music version of Eternal Sunshine of the Spotless Mind. You know how a relationship ends, and yet you wouldn’t give up your memory of it because you cherish the good parts too much.
15. “Concrete Angel,” Martina McBride
This soul crusher from Martina McBride is about a little girl suffering from child abuse. Some of the people around her start to notice but fail to report it, and she dies. She then goes to the afterlife, where she finally receives the love she deserves.
16. “Angel From Montgomery,” John Prine
There is so much unrequited longing in this 1971 classic from John Prine that it’s hard to listen to without feeling like you too are an old woman dreaming that someone will come take you away from your unhappy life. See also: Bonnie Raitt’s 1974 version from her album Streetlights.
17. “Top of the World,” Patty Griffin
The Chicks won a Grammy for their version of Patty Griffin’s lament, which tells the story of a man reflecting on his regrets near the end of his life. Griffin’s recording of the song appeared on her 2004 album, Impossible Dream, after it was originally written for 2000’s Silver Bell (which didn’t get released until 2013 because of a label dispute).
18. “In Your Love,” Tyler Childers
While it’s possible to intuit a happy ending from the lyrics of “In Your Love,” the music video offers no such respite, telling the story of two gay coal miners whose romance ends when one dies suddenly at a young age.
19. “I’m So Lonesome I Could Cry,” Hank Williams
No list of sad country songs would be complete without Hank Williams, who really outdid himself with this all-timer. Even if you’ve never heard a lonesome whip-poor-will, Hank will make you feel like you have—and that’s why this song still hits nearly 75 years after its debut.
20. “Tin Man,” Miranda Lambert
Never has a Wizard of Oz reference hit harder than this ballad from Miranda Lambert’s 2016 double album, The Weight of These Wings. Sample lyric: “By the way there, Mr. Tin Man / If you don't mind the scars / You give me your armor / And you can have my heart.”
21. “Always on My Mind,” Willie Nelson
When choosing a sad Willie Nelson song, it’s a real toss-up between this one and “Blue Eyes Crying in the Rain,” but “Always on My Mind” wins out for the way his voice wavers with regret from note one.
22. “Hello Walls,” Faron Young
Popularized by Faron Young but written by Willie Nelson, “Hello Walls” is a song about being so heartbroken you can’t do anything but talk to your own walls and windows. If you thought crying into your beer was bad, then think about having a one-sided conversation with your ceiling.
23. “Mercy Now,” Mary Gauthier
It’s a shame that Mary Gauthier isn’t more famous than she is, because she can write a weepy ballad like nobody’s business. “Mercy Now” from her 2005 album of the same name represents some of her best, most heartbreaking work.
24. “Down From Dover,” Dolly Parton
Perhaps it’s unfair to put Dolly Parton on the list twice, but she’s written literally thousands of songs in her life, so if anyone deserves two entries, it’s her. Released in 1970 on Parton’s album The Fairest of Them All, “Down From Dover” tells the story of a teenager whose lover deserts her after he gets her pregnant. She hopes all the while he’ll come back to her, but he doesn’t—and the tale only gets bleaker from there.
Related: Dolly Parton’s Net Worth In 2023 Is Fit for a Country Queen
25. “Hurt,” Johnny Cash
Johnny Cash sang plenty of heartbreakers in his career, but his 2002 cover of the Nine Inch Nails song “Hurt” was so poignant that Trent Reznor himself said, “That song isn’t mine anymore.” Adding to the Cash version’s resonance is the fact that the country icon died at age 71 just seven months after the single’s release.
