What's The Saddest Country Music Song Ever Made? Intense Debate Rages Online
George Jones' "He Stopped Loving Her Today" is a classic example of a sad country song.
A debate is raging online about the saddest country song ever made, and the answers are pretty fascinating.
It's no secret that I'm a huge country music fan. It takes all of five minutes of reading the stuff I write to figure that out.
There's something about a great country song that hits differently. I'm not talking about that pop trash that has become popular over the past decade.
I mean real country music, and that includes all the sad songs made over the years.
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Country music is a great genre of music that has produced plenty of epic songs over the decades. (Photo by Michael Hickey/Getty Images)
Internet debates saddest country song.
It seems a debate pops up at least once a year online about the saddest country songs ever made, and it never disappoints.
Whiskey Riff discovered a Reddit thread popping off on the subject. You can read some of the answers below, and then I'll give you guys my take:
- He Stopped Loving Her Today - George Jones
- Sam Stone - John Prine
- She think his name was John- Reba
- Alyssa Lies by Jason Michael Carroll deserves a shout out
- Whiskey Lullaby - Allison Kraus and Brad Paisley
- The Reckoning - Whiskey Myers
- Evangeline - Turnpike Troubadours
- Ballard of Ira Hayes- Johnny Cash
- May be a bit too modern, but Cloud of Dust, You'll Never Leave Harlan Alive and Whiskey Lullaby by Brad Paisley
- Blue Eyes Crying in the Rain by Willie Nelson
- Brother Joe - Ole 60
- Well since you posted Hank, Im So Lonesome I Could Cry is my nomination. Simple, but raw and haunting. The amount of emptiness he evokes w a couple of lines about birds is mastery.
- Finger on the trigger - Bleu Edmondson
- David by Cody Jinks makes me bawl. There’s sooo many other good ones too though
- Riding with Private Malone- David Ball, I never see it on these lists, so maybe it's just me, but it makes me cry
- Maggie’s Song - Chris Stapleton
- Jamie by Zach Bryan and CWG
- The Beaches of Cheyanne - Garth Brooks
- If Your Reading This…Tim McGraw
- Whiskey Lullaby
- The Road Goes On Forever - The Highwaymen. Not the most obvious choice but the guy ends up on death row.

Country Music singer George Jones' "He Stopped Loving Her Today" is considered one of the most popular country songs ever made. (photo by Beth Gwinn/Getty Images)
Lots of good answers there, with a couple of repeats showing up for obvious reasons. My opinion on this topic remains pretty fluid and open.
It depends on the mood you catch me in, but I think there's always been two clear ones that stand out above the rest.
"David" by Cody Jinks and "Whiskey Lullaby" by Brad Paisley are incredibly hard to beat in terms of country music songs.
The song by Jinks tells a story the listener can tell is going to end in absolute tragedy long before it does, and it speaks to the struggles of working-class people in rural America.
It also shows how the simplest of choices can send people on very different paths in life.
As for "Whiskey Lullaby," the song turned Brad Paisley into a legit star more than 21 years ago. It's hard to believe it's already been more than two decades since the track was released.
Alison Krauss' vocals are damn near chilling.
I could sit here all day with more examples, but those two will always be near the top of the list for me. Do you have a country song you find particularly sad? Let me know at David.Hookstead@outkick.com.