17 More Sad Country Songs

There was no more holding out. I had to add to the list of Sad Country Songs. It’s been the most popular series in the history of CML and with all of the suggestions for more sad country songs I thought I’d put together another post with more songs.

These include every song you’ve mentioned in the comments along with a few others I thought fit the sad situational country songs.

It’s not that we want to be sad all the time, but when we’re feeling a little down these are the songs that help us know we’re not alone in the world. Country music has always had a way with sadness and these are more of the songs that make it the best genre of music.

So with a little tip of the hat to George Strait and his 22 More Hits album we continue with…

17 More Sad Country Songs

1. Whiskey Lullaby – Brad Paisley & Alison Krauss

Brad PaisleyThis was the most requested addition to this list. In 2004, Brad Paisley and Alison Krauss had an unlikely it with Whiskey Lullaby. The song about a double suicide kind of surprised a lot of people since the subject isn’t really made for a safe country song. Brad and Alison really made this a great track as they took the story and added the emotion necessary to tell it. It’s a huge song and one that definitely belongs on the list of the saddest country songs of all time.

2. Chiseled In Stone – Vern Gosdin

Some of us get lucky in life. Some of us get the chance to learn from the life lessons of others. With his well known song Chiseled In Stone Vern Gosdin played the role of a guy that gets a second chance. The narrator has an argument with his woman. He heads to the bar where he finds an old timer. The guy he meets tells him he ought to feel lucky. He has someone to go home to. He tells him he’ll never know lonely till it’s chiseled in stone on her grave. Now that’s a warning and it’s too bad it came for the old man in the bar.

3. Probably Wouldn’t Be This Way – Leann Rimes

Leann RimesThere are a lot of opinions about Leann Rimes these days, but all I care about is the fact that she can sing the hell out of a country song. As Leann came into her own as an adult singer she really found a great song with Probably Wouldn’t Be This Way. It’s the story of a woman trying to move on from the loss of her lover. She’s looking at going out on dates, but she can’t take herself away from the one she’s lost. She sees him at his grave and just has the hardest time moving on. It’s sad, but that’s how life is sometimes. It’s a great track.

4. I Sang Dixie (As He Died) – Dwight Yoakam

It’s hard to believe I left Dwight off the list the first time around. He’s classic country and a few of hits should qualify as pretty sad country songs. With I Sang Dixie Dwight sings about the loss of his good friend. He just sings Dixie as his buddy passes on. It has to be sad to see someone you love slip away to the next life. It’s something that happens to all of us at some point in life and with songs like this we know we’re not alone.

5. Today My World Slipped Away – George Strait

George StraitDivorce is getting common these days. It’s hard to know if people are really falling out of love or if they’re simply getting married too soon. Whatever the reason there is no doubt divorce is common. George Strait sang about divorce with his song Today My World Slipped Away. It’s the story of a couple at the courthouse making things final. The woman is ready to move on, but the guy isn’t really ready. He feels like his entire world is getting away from him. He’ll probably be alright, but right now he feels like he has nothing. Now that’s a sad song.

6. Baby’s Gotten Good At Goodbye – George Strait

This is the second George Strait song on this additional part of the list. George can really sing about anything and make it have an impact on the listening audience. Back in 1989 he took the somber route and really had himself a big hit with Baby’s Gotten Good At Goodbye. It’s the classic song about a guy not being up to a woman’s standards. She leaves and he’s left alone. I guess it’s become a classic sad country song, but George always seemed to be an original.

7. Almost Home – Craig Morgan

Craig MorganBack in 2002 there weren’t a lot of people that knew about Craig Morgan. He knew he had the potential and it just took that one breakthrough hit to really get the attention of the general country audience. The song was Almost Home and it really became a surprise hit during its run on the charts. It’s about a homeless man that kind of inspires the narrator of the song in a way. Things begin pretty sad in this story and eventually work out to the understanding that life is too good to throw away.

8. Sissy’s Song – Alan Jackson

Alan JacksonAlan Jackson released this song back in 2009. It was his tribute to his late housekeeper. Alan has released plenty of somber tunes in his 20+ years of hit making, but this one had a different sound to it. Alan really poured emotion into this track and it’s obviously because he felt strongly for his lost friend. We all suffer difficult losses in life and even if we hear a song about someone else we can always put our own stories into the context.

9. Dear Me – Lorrie Morgan

Lorrie Morgan can still sing a country song. She’s one person I’d love to see in concert and I hope I get the chance someday soon. With songs like Dear Me Lorrie really showed just how special her voice is. She could sing the hell out of a sad country song. Dear Me is about a woman that’s lost her man. She screwed things up and now he’s gone and probably for good. She’s only realizing now that he’s gone just how good they were together. All the plans are out the door and life is going to be different. That’s a sad feeling.

10. If You Came Back From Heaven – Lorrie Morgan

With this track Lorrie sings about love and loss. The track is about the love of her life leaving her. There is a ton of sadness in the story and plenty of emotion in Lorrie’s vocals. She’s one of the best singers of all time and hearing her sing about maybe having the one chance to see her loved one again is enough to bring tears to your eyes.

11. The Last One To Know – Reba McEntire

RebaOften in relationships there is one person ready to move on while the other is obliviously to the waning of love. It’s not really being oblivious as much as it is about just not seeing what is right in front of you. That was the case for the narrator in Reba’s song The Last One To Know. She didn’t see things coming. She didn’t realize she was in a dying relationship. There is no one better than Reba. She can sing any kind of song and that includes a classic sad country song.

12. Don’t Close Your Eyes – Keith Whitley

If you want sad country songs you need to listen to the classic hits of Keith Whitley. The man seemed to have ┬ásad life if you just listen to his collection of songs. One of the tracks that really hit home with country fans was Don’t Close Your Eyes. This song really cemented Keith’s status as a rising country superstar. It’s about a man that knows his woman doesn’t really love him. All he wants is for her to think of him and keep her eyes open when they’re intimate. It’s a sad situation and one most of us hope to never be in.

13. All The Good Ones Are Gone – Pam Tillis

There is something about being 30 years old that drives women nuts. I can’t say what it is since I’m a guy, but when women turn 30, especially if they aren’t married and don’t have kids, they go a little crazy. There must ben some kind of clock in their head that makes them think about if they’ll ever find love and be able to have a family. I suppose it’s a little sad depending on the situation and it’s just the sentiment Pam Tillis sang about with her big hit All The Good Ones Are Gone. This song still makes me feel a little sad and I’m not even a woman. It’s just a great track from one of my all time favorite artists.

14. Cryin’ For Me (Wayman’s Song) – Toby Keith

Toby KeithIn late 2009 Toby Keith kind of caught everybody off guard with his sad country song Cryin’ For Me (Wayman’s Song). The song was Toby’s tribute to the late basketball superstar and jazz musician Wayman Tisdale. The two had formed a relationship around their love for music and when Toby got the news about Wayman’s death he sat down and did what he does best – write a great country song. For fans the song had to catch them off guard a bit. Toby is usually all about bravado and masculinity, but we see the softer side of him on this emotional song.

15. 21 to 17 – Doug Supernaw

When we think back on the impact artists of the 1990s we don’t often include Doug Supernaw. And it’s not our fault. Doug had something special going after a run of successful albums and albums, but he threw it all away when he couldn’t keep control of his life. That’s how things work out sometimes. In late 1999 we got our last bit of country music from Doug. He released the track 21 to 17 and even though it didn’t chart the video for the song saw some play on the country channels. It’s a song about a young couple that finds themselves breaking up just as the local high school football team wins their homecoming game.

16. When She Cries – Restless Heart

By 1992, Restless Heart had lost their main lead singer and were probably wondering if they couldn’t continue their run at the top of the country charts. All worry subsided when the band released what is often considered their biggest hit – When She Cries. The song shot into the country top ten and became a crossover hit on multiple charts including pop and adult contemporary. The song is about a man that realizes he’s making his woman sad to be with him. She’s crying and he’s sad about making her cry.

17. Lucille – Kenny Rogers

Kenny Rogers was nearly 40 years old when he had his first solo number one hit in 1977. The song was Lucille and country fans couldn’t resist the catchy chorus and the sad nature of the song. It’s a story told by a guy that meets a woman in a bar one night. He introduces himself to a woman sitting just down the bar. The woman’s husband comes along and the guy thinks he’s a dead man. Then out of nowhere the husband gets really sad and tells Lucille about how she’s left him at just about the worst possible time. There are a lot of emotions in this song and if you’ve ever been in the husband’s shoes you know it’s sad.

Entire List

The Saddest Country Songs of All Time

The Saddest Country Songs of All Time Part 2

The Saddest Country Songs of All Time Part 3

The Saddest Country Songs of All Time Part 4

The Saddest Country Songs of All Time Part 5

Dayne Shuda

Founder of Country Music Life. Follow on Twitter: @dayneshuda Follow on Google+: Dayne Shuda

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  1. David says

    Great list! But how can you omit Doug Stone’s “I’d Be Better Off (In a Pinebox)? That’s gotta be the most depressing song of all time.

    Another less known song is Dusty Drake’s “One Last Time”. It’s got a 9/11 theme and breaks me down everytime.

    I love country music because it’s so emotional.. any emotion. Thanks for the list and keep up the good work!

  2. says

    David…I love Doug Stone and you’re right. That song deserves to be on here (and probably a couple of his others).

    I’ll have to put another list together soon.

    Thanks for suggesting :)

  3. brent n says

    I like this list but there is a song missing entitled “custody”. I can’t remember who sings it but it will jerk the tears! It is an older song prolly 70’s thanks

  4. Derrick says

    you have a lot of good sad songs but you failed to mension the song that i feel is the saddest ever Teddy Bear by Red Sovine

  5. Dee says

    Don’t forget about baby blue by George Strait, and the baby by Blake Shelton. Not to mention just to see you smile by Tim McGraw. Those are a few songs that always leave me teary eyed!

  6. Rozanne says

    Don’t forget some of the oldies, such as:

    Dan Seals – Addicted
    Con Hunley – They Never Lost You
    Earl Thomas Conley – What I’d Say
    John Conlee – Holding Her and Loving You

    I always LOVE finding new country songs that I haven’t heard before. “A House with no Curtains” was new to me!
    I LOVED reading your posts! Thanks =)

  7. Edith says

    No one ever seems to remember “Waitin’ on Joe” by Steve Azar – wow – I can hardly listen to it without tearing up.

  8. Dayne Shuda says

    Great song, Edith. I still have that album. Very underrated song and full-length album.

  9. Phil barrett says

    No ken mellons, daryle singletary, johhny paycheck? Give me a break, Steve azar? Some of the best singers aren’t even on the list just because their not mainstream. Learn country music first before you make a list. This list is laughable, Vern gosdin would be in top 5 easy, mellons “I can bring her back”, tear jerker. Paychecks “old violin” is #1 on my list but I’m sure most never heard. It’s ok because “real country fans” know ” real country”

  10. says

    Looking for the lyrics to a country song after the war titled “No Children Allowed”. A song about a returning soldier that no matter where he goes to find a home for his family, he is met by “No Children Allowed”

  11. Greg says

    I am looking for a special song I heard in the late 1990’s. The timing for me was right. I had just lost my wife to cancer and this song came on the radio. It was about a man losing his wife to cancer and they had a daughter who he was then raising. He tries to explain the loss to her but she ends up telling him that her mother is looking in on both of them. I thought maybe a Tim Mcgraw song but I am still trying to find who wrote it and who sang in it came out around 1999 I think. Anyone know the tune?

  12. Dayne Shuda says

    Hi Greg. That’s a tough one. My best guess would be Holes In The Floor Of Heaven by Steve Wariner, but it doesn’t match the story perfectly.

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