The Saddest Country Songs

The Boot has published another  list that’s got me thinking. This time, it’s Top 10 Sad Love Songs in Country Music.  Again, the title is a bit strange, as the list includes the Suzy Bogguss hit “Letting Go”, which is about a mother watching her daughter go off to college, but there’s no rule that a love song has to be about romantic love, I guess.

Predictably and justifiably, the list is topped by “He Stopped Loving Her Today”, a George Jones classic that tops many a classic country list, including one of our own.  There’s also a pretty high body count – four outright deaths and one by implication.  Country songs sure do like to kill people off, don’t they?

So what are the saddest country songs ever?

My first instinct was to mention “Where’ve You Been”, but that Kathy Mattea classic has a ray of hope. It’s really about a perfect relationship meeting its natural end.

For real, heartbreaking sadness, all hope must be vanquished, with only regret remaining. Bonus points if somebody dies.  Here are two that I think are tragic, one with death and one without:

Dixie Chicks/Patty Griffin, “Top of the World”

A man realizes after his death that he did nothing but hurt the woman he loved, and now it’s too late to go back and change it:



John Conlee, “Backside of Thirty”

Something similar, though the man is still alive. He had everything he ever wanted – a beautiful wife and son – and somehow messed it up. He’s now living alone in an apartment, drinking away his rent money, “back on the bottom with no will to climb.”


What do you think are the saddest country songs ever?


  1. Some of my favorite sad songs:
    Wynonna – Is It Over Yet
    Vern Gosdin – Chiseled in Stone
    Vern – Today My World Slipped Away
    Alan Jackson – Monday Morning Church
    Possum – The Grand Tour

  2. Two Chris Ledoux songs come to mind. “Blizzard” is about a man riding home during, you guessed it, a blizzard. He wills his horse along until 100 yards from home his horse can’t go any more. Rather than leave his horse to die alone, he freezes to death beside “ol’ Dan.” The second is “Silence on the Line” about a rodeo cowboy who wants to come home. The heartbreaking twist comes in the third verse.

    The saddest song I’ve ever heard however is “The River” by Bruce Springsteen. It’s message of lost dreams is really scary to me, an idealistic 20 year old.


  3. The very first song that came to my mind is Sunday Morning Coming Down. I can never hear Kris’s broken, lonely version and not feel melancholy myself. It’s the anthem of people who have given up, resigned themselves to having nothing.

    I ripped the audio off of this version and put it on my iPod — great stuff.

  4. “Chiseled in Stone”–Vern Gosdin
    “It Turns me Inside Out”–Lee Greenwood
    “A Good Year for the Roses”, especially the George duet with Alan Jackson

    Saddest song by a Woman: “D-I-V-O-R-C-E”
    Saddest song by a Group/Duo: I’ll get back to this after more thought.

  5. I don’t think it’s the saddest country song, but when you pair it with the video it brings a tear to most people’s eyes, What do you say by Reba.

    Also, For My Broken Heart and If I Had Only Known by Reba are classic sad songs.

  6. “The Bridge”, “Down From Dover”, and “Mountain Angel” by Dolly Parton; “Boulder To Birmingham” by Emmylou Harris; “Mr. Pain” by The Judds; “Wake Up Older” by Julie Roberts; “Misty Blue” by Reba OR Lorrie Morgan OR anyone who sings it really; “If Wishes Were Horses” by Lucinda Williams; “Cheap Whiskey by Martina McBride; “Sorrowful Angels” by Patty Loveless; “What About The Love We Made” by Shelby Lynne; “Talking To Myself Again” by Tammy Wynette; “On A Bus To St. Cloud” by Trisha Yearwood, and “Is It Over Yet” by Wynonna are all songs I consider to be among the saddest of all time.

    For me, however, the saddest of them all is “Only In My Mind” by Reba, mostly because of her gut-wrenching delivery.

  7. A few that come immediately to mind:
    Chiseled In Stone and Monday Morning Church, both suggested by Trailer
    Whiskey Lullaby
    Patty Loveless’s Sorrowful Angels, where even the angels are crying
    Lots of George Jones

  8. There’s two songs that stand alone atop the list, both suicide notes

    “The Last Letter” by Rex Griffin. Many later singers such as Waylon Jennings left off the last (4th) verse completely which changes the meaning of the song completely from a stark tragedy to such more of a typical country lament. The best recording of this song was by Jack Greene but Glen Campbell did a terrific job with the song, and other singers havebeen effective with it too. Remember — the song has four verses – if only the first three are performed you’ve missed the impact of the song

    “Farewell Party” written by Lawton Williams, originally a regional hit for Little Jimmie Dickens in 1963 but later a monster for Gene Watson

    “you’ll be free at the end of my farewell party – but I’ll leave this world loving you”

    Behind these two songs, I would put Hank Williams’ “I’m So Lonesome I Could Cry”,Vern Gosdin’s “Chiseled In Stone” and the George Jones Classic “When THe Grass Grows over Me”

  9. I have to agree with Greg–“For My Broken Heart” and “If I Had Only Known” by Reba has to top the list for me. That entire album is just incredibly depressing. Trisha’s “On A Bus to St. Cloud” and Le Ann Rimes’ “Probably Wouldn’t Be This Way” would also get votes from me.

  10. For me “Whiskey Lullaby” can always sap all of the happiness out of me.

    Alan Jackson’s “Here in the Real World also always makes me feel sad, as does Keith Urban’s “Tonight I Wanna Cry”.

    Brad Paisley’s “Cloud of Dust” may not be a “love” song, but I also feel sad listening to it.

    There are so many… :’)

  11. Chiseled In Stone – Vern Gosdin
    I Can Still Make Cheyenne – George Strait
    Long Black Veil – John Anderson (my fav cover)
    Still – Reba
    When Love Fades – Toby Keith
    Whiskey Lullaby – Brad Paisley
    Today – Gary Allan
    When Love Dies – Brooks & Dunn

  12. Saddest country song ever HAS to be “Down to Seeds & Stems Again” (the original from Lost In The Ozone) by Commander Cody & his Lost Planet Airmen.

    Another contender – “Wild Irish Rose” by George Jones and for over-the-top sadness, George singing “Things Have Gone To Pieces”.

    Have to agree with Vern the Voice’s “Chiselled In Stone” and “On A Bus To St Cloud” (I like the original by Gretchen Peters);


    Iris DeMent’s “Easy’s Getting Harder Every Day”.
    Patty Griffin – “When It Don’t Come Easy”

    And a hundred more I can’t recall at this moment…

  13. I think what I consider the saddest country songs and the country songs that make me the saddest are probably two different things. One of the saddest lines I’ve heard in the past few years is the bridge of Lady A’s “Things That People Say,” in the context of divorce: “Well my mama won’t stop crying/She wonders what went wrong/Could I have loved a little deeper?/Did I hold on too strong?” To me, there’s something indescribably sad about a mother being affected by and trying to make sense of her child’s pain. (Happy Mother’s Day to all the mothers!)

  14. …dwight yoakam’s “johnson’s love” from his “hillbilly deluxe” album is a real gem in this context. furthermore, i’d add johnny cash’s “green green grass of home”, lorrie morgan’s “good as i was to you” and not to forget garth’ “cowboy bill” or ashton shepherd’s “how big are angel wings”.

  15. How on earth could I forget “Melancholy Blue”? Rebecca Lynn Howard did a good original version on her debut album, but Trisha OWNS that song, no doubt

  16. 1. Long Black Limousine — recorded by many people but Keith Whitley’s version is my favorite
    2. The Grand Tour — George Jones
    3. Where Do I Put Her Memory — Charley Pride
    4. Down From Dover — Dolly Parton
    5. More Than A Name On A Wall — The Statler Brothers

  17. Chris Young – Flowers

    New artist. Album cut from his first cd.

    Man kills lover drunk driving.

    I still see you on your knees
    Begging me not to drive
    But I took away the keys
    And made you climb inside
    And I’d take your place in this field of stone
    If I only had the power
    Look what it took
    For me to finally bring you flowers

  18. One that comes to my mind (not really a country song per se, though it was recorded on Music Row forty years ago) is “Long Long Time”, Linda Ronstadt’s first solo hit, from 1970. Linda, of course, is no stranger to songs about unrequited love, but how about the memory of an unrequited love that never existed? If that’s not a unique twist to a sad song (one that actually wore Linda out just recording it), I don’t know what is.

  19. Pirates of the Mississippi’s “Feed Jake” I heard brought George Jones to tears. I’d say that is the definition of sad right there.

  20. “Top Of The World” is one of the most haunting I have ever heard.

    I’d also second Trisha’s “On A Bus To St.Cloud”. A lot of Reba’s For My Broken Heart album has some, one of the saddest is “I Wouldn’t Go Far”, the woman in the story chooses to have a succesful career but gives up the chance at love in the process.

  21. “I Wonder” – Kellie Pickler

    Gets me almost everytime =)


    “The House That Built Me” – Miranda Lambert

  22. In the Lambert song, The line about the dog gets me everytime, which is probably why I chose “old Shep” as the saddest song ever.

  23. By the way, Kevin, thanks for reccing “Top of the World”. I can’t stop listening to the Patty Griffin version. It’s so heartwrenchingly gorgeous.

  24. Top of the World
    Have you seen that girl – Lee Ann Womack (It’s just really sad for some reason)
    Concrete Angel – Martina McBride
    Roll me back in time – Sara Evans
    And Whiskey Lullaby.

  25. I have a question for the bloggers. Do Bloggers stick together or are they willing to criticize each other? What I mean is: look at Alison Bonaguro. She writes some of the most ignorant and badly reasoned things on the Internet. But do bloggers call her out or defend her? I know bloggers will make fun of bad songs and bad songwriters, but will they make fun of bad Bloggers like Alison Bonaguro? If its ok to make fun of bad country music like “BOMSHEL” , why not make fun of bad Internet writers? But maybe bloggers stick together and defend each other. I don’t know. By the way, I think John Conlee’s “Miss Emily’s Picture” is pretty dern sad.

  26. Smoke Rings in the Dark – Gary Allan
    Go Rest High on That Mountain – Vince Gill
    Diamond Rio – You’re Gone
    John Michael Montgomery – Friends
    Jeff Carson – The Car

  27. A few others I haven’t seen yet…

    Reba – Greatest Man I Never Knew
    Doug Stone – I’d Be Better Off (In a Pine Box)
    Clint Black & Wynonna – A Bad Goodbye
    Brooks & Dunn – It’s Gettin’ Better All the Time
    George Strait – I’d Like to Have That One Back
    John Anderson – I Wish I Could’ve Been There
    Trisha Yearwood – This is Me You’re Talking To

    And for whatever reason, this song gets me…

    Tim McGraw – Red Rag Top (just slightly more than “Just to See You Smile”, “Can’t Be Really Gone”, and “Don’t Mention Memphis”).

  28. Pretty much every song Alison Krauss has ever recorded! “Jacob’s Dream” definitely comes to mind, made all the sadder by the fact that it’s based on actual events.

  29. Remember when by Alan Jackson makes me cry every time! Especially when you can relate it to your life. Red on a rose by Alan Jackson, Today by Gary Allan, What hurts the most by Rascal Flatts are just a few.

  30. Of all the songs the Dixie Chicks ever recorded, I can’t think of any that would leave as much of a lasting impact as “Top of the World.” The string section is enough to give you chills!

    I had never seen the music video before – thanks for including it. It really brings the story to life (and Natalie looks so pretty in the video!).

  31. My favorite sad song is probably Trisha Yearwood’s “On a Bus to St. Cloud”. I had heard once that it was written from the persepective of someone who is left behind after their lover commits suicide. Has anyone else ever heard that story or interpreted it that way?

  32. Steve Earle’s “Goodbye.” The idea of not even being able to remember is you said goodbye to someone you’ve loved and lost….

  33. Carrie Underwood’s “Just a Dream” – this one really hits home for me, personally. Plus, the raw emotion she puts in the song really gives you the chills.

    Trisha Yearwood’s “Dreaming Fields”
    Brad Paisley & Lee Ann Womack’s “Whiskey Lullaby”
    Tim McGraw’s “Can’t Be Really Gone”
    Reba McEntire’s “I Wouldn’t Go Far”

  34. Thanks for starting this thread! There have been a lot of great responses, and now I have a lot of new music to listen to find (and cry over).

  35. Has anyone seen Country Strong? I was never much into country music, but it inspired me to explore the genre, and it’s a gift that keeps on giving! So far haven’t found too many sad songs, but I’m going to check out some of the tracks on this list.

    You know, so I can feel sad. :)

  36. I used to hang out at a karaoke bar on Fridays, and a woman sang ““D-I-V-O-R-C-E” every time, after midnight, and after a few pints. She cried every time.

  37. I know it’s been said a few times, but when I was feeling sorry for myself, I listened to “Chiselled In Stone” over and over. Funny how you want to wallow in sad songs when you’re sad…

  38. @Mike Johnston:

    I was reading through the list, and I practically started crying when I just saw the title: I’d Be Better Off (In a Pine Box)

    Doesn’t get much sadder…

  39. although only very few teens can appreciate country songs (except the songs by taylor swift), I remained loyal to this genre because I believe they make more sense.. compare “A Bad Goodbye” by Clint Black and “friday:” by rebecca black..

  40. I think the saddest country song is Ronan by Taylor Swift. Its about this 4-year old boy who dies of cancer. The saddest thing is that this is a true story. Taylor co-wrote it with Ronan’s mother Maya. Its so tragic. Taylor cried while she sang it at the 2012 Stand Up To Cancer telethon. Listen to it. You will probably cry a river after like I did.

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