Artist Picks: Sad Songs

We’re kind of clingers to sad ol’ songs, and we’ve got some friends that are too, so we’ve compiled our favorite sad country songs! Let’s get sad, y’all.

Alexis May

Down From Dover- Dolly Parton

Dolly has never been afraid to tell a painful story. The narrator of this song has been hurt and betrayed, and is now left with a baby on the way. Dolly sings this in a way that makes me believe that this story is close to her heart, and the haunting pedal steel cuts like a razor through this song. I’ll never forget buying this album and hearing this for the first time; I had chills all over my body.

Ain’t No Time to Go- Loretta Lynn

Right now, more than any time before, this song finds a way into my heart and shatters it. She sings about someone who is passing, begging them to stay. After losing my great grandmother last year (who also loved Loretta), I haven’t been able to hear this without getting teary-eyed. Now with Miss Loretta gone, this song is a reminder of how much the county music community needed her.

Promises- Randy Travis

“Promises” is about a man who swears he will change his ways and stop cheating. I love this song because it has a painful honesty from a voice that carries so much emotion. He admits his faults, and beyond that, admits to knowing he will break her heart again until she finally can’t stand it. The narrator of this song is probably supposed to be the bad guy, but by the last verse, I sympathize for him. 

Help Me Make it Through the Night- Kris Kristofferson

I’ve never never heard a version of this song that I didn’t like. I think that Kristofferson did such a fantastic job of capturing the raw emotion of one person wanting another for the sake of killing a lonely feeling. For me, this song can break or mend a hurting heart. Somehow, when I feel alone, these lyrics let me know that I’m not the only one who has ever felt this way.

Hungover- Brandy Clark

One of the hardest things a person can do is outgrow someone they love. This song tells a story about someone learning about who they are and bettering themselves, while they watch a loved one continue to drink their life away. I heard this song for the first time when I was 17, right before leaving my hometown to start life on my own. I’ve changed a lot since then, and it’s strange to see that some things haven’t, just like this song says.

Shelby Lee Lowe

Chiseled in Stone- Vern Gosdin

This song is powerful. The story, the melody, the voice and the production hit me in the soul every time I hear it. It’s a beautiful and sad reminder to make the most of everyday with the people you love, because someday, they will be gone.

He Stopped Loving Her Today- George Jones

This song is most likely number one on most folks’ list, and I can’t argue with them. I’ve seen grown folks break down and cry in public hearing this song. It’s hard to beat the Possum.

I’m So Lonesome I Could Cry- Hank Williams Sr.

This is one of the most beautifully poetic sad songs ever composed. It’s no wonder they called him Hillbilly Shakespeare.

An Empty Glass- Gary Stewart

This song is pure heartache. There’s not much of a story to it. just a song about a man who is helplessly drinking his pain away. The melody and the performance by Gary Stewart is what sets this song apart as one of the saddest songs of all-time.

Misery and Gin- Merle Haggard

Merle has some killer sad ballads, but this song just hits different. It’s a man in a bar missing the woman he loves while pretending to be happy. If you’ve ever been there, you can’t not feel this song in your soul.

Hershell Golden

Wish You Were Here- Mark Wills

This may very well be my favorite written song of all time. I’ve always been drawn to songs that have a good twist in the story line. What initially seems to be a typical “love song” ends up with a tragic but reassuring feeling of how true love never dies. I’m not crying, you’re crying [laughs]. 

Ships That Don’t Come In- Joe Diffie

I absolutely love this song’s arrangement, writing and delivery! The story starts with two gentlemen who are down on their luck having a heart-to-heart conversation, but are appreciative to have received some opportunities in life that so many others never had. It’s somewhat of a reality check every time I hear it, and a reminder to be thankful for all the blessings in life. 

I Know She Still Loves Me- George Strait

You can’t ever go wrong with a good ol’ George Strait ballad, and this one has always been a favorite of mine. I’m very happy this song has no significance to myself, but I can see how many people can relate to it. It just goes to show you how a relationship, no matter how much you love one another, can slowly deteriorate, and there’s nothing you can do about it. The love is there, but the spark is gone. It tears my heart out for the poor guy in the storyline every single time. 

She Was- Mark Chesnutt

Wow. To say this song is deep would be an understatement. I’m glad Mark was pitched this song, because he absolutely nails it! I’m not sure what else to say about it other than if you haven’t heard it, then do yourself a favor and give it a listen. Keep the Kleenex nearby! [laughs] 

What Am I Gonna Do (With the Rest of My Life)- Merle Haggard

Classic Merle Haggard right here! Through the years of playing honky-tonks and bars, I’ve noticed many men and women that I can guarantee were going through the same struggles Merle writes about in this song. Sometimes losing a loved one, either through break-up or death, can make a person fall off the deep end if you will. Maybe turn to drinking, drugs or whatever puts a temporary band-aid on the situation, all the while knowing it is not their best option to cope, but it sure helps at the time. Mighty Merle kicked it out of the park with this one! Arguably the best country song written to date in my opinion. 

Darby Sparkman

I am no stranger to storm clouds spitting rain on the brim of my black felt hat. In fact, I spend most of my creative time reveling in the fact that sadness is something every human experiences, no matter where their bootjack is. 

When we sit and think of the greatest country songs ever written, I’m willing to bet there’s a higher percentage of sad songs on that list than any other. 

Let’s take a gander at my top five saddest country songs ever (that also happen to be my favorite!)

That Kind of Lonely- Patty Griffin

This song rips out my soul and lays it on a tarnished silver platter. 

I’d Be Better Off (In A Pine Box)- Doug Stone

Seeing the one who broke your heart with someone new, nothing worse could ever happen. Losing yourself over losing your love is certified sad. 

Does He Love You- Reba McEntire ft. Linda Davis

Fighting the other woman for who is loved more? This song (and their beautiful voices) rips my heart right in two. 

It Won’t Always Be This Way- Kaitlin Butts

This story hurts my feelings. It feels so close to home that it almost feels like Kaitlin is talking about my life. I don’t want to interpret the story for you, you’ll just have to listen and be prepared to cry. 

Beaches of Biloxi- Mike and The Moonpies

Having to tell your wife that you can’t start a family because you’ve gambled away all the money you two had? What’s sadder (or more country) than that? 

I can’t cram every sad song I love into this little article, these are just the ones I’m currently listening to!

Justin Loretangeli (Pro Country)

If you follow Pro Country on social media, you know how much I love a good sad song, so I had to join in as well!

Family Reunion- Wade Hayes

Man, can Harlan Howard write a song. As much as we’d like it to be, not everyone has a picture-perfect family dynamic, and this song paints that picture in an absolutely heartbreaking way.

Whiskey Lullaby- Brad Paisley featuring Alison Krauss

For my money, this is the saddest country song ever written. Is there a better opening line than “She put him out like the burning end of a midnight cigarette”? I mean, come on.

A Man’s Home is His Castle- Faith Hill

The first time I heard this song, it stopped me dead in my tracks, so much so that I spent literally an entire year trying to track down the sole songwriter to ask her about it. Domestic violence isn’t a topic that gets tackled too often, and Faith delivers the true story in devastating fashion.

Flowers- Chris Young

Man. This one will rip your heart out, chew it up and spit it on the ground. The hook will shatter you (in the best way) and make you think twice about getting behind the wheel when you’ve had a few.

He’ll Be Back- Lee Ann Womack-

If you put me on the spot, I’d say that Lee Ann Womack has the best female voice in the history of country music. Is there anything sadder than trying to move on from an old flame but their memory keeps sticking around?

Just for the Record- Ruston Kelly

I tried to whittle my list down to five songs, but I’ll have to break my own rules and include a sixth. Ruston Kelly’s vocal delivery is heartbreakingly haunting. Realizing you’re not enough for someone you love is enough to chill you to the bone.

Follow Alexis, Shelby, Hershell and Darby on Spotify!

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