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And The Saddest Country Song Of All Time Is…

Whiskey Riff
Whiskey Riff
Beth Gwinn via Getty Images

We asked. You voted.

And now the results are in.

We asked you to vote on what you thought was the saddest country song of all time. Not your favorite sad country song, but the saddest song of all time, the one that you can’t listen to without your eyes getting misty.

And boy did you respond.

We got over 4,700 votes, including a ton of great write-in submissions. People love their sad country music.

So before we get to the song that you voted the saddest of all time, let’s take a look at some of the other results.

The Write-Ins

There were a couple of songs that got enough write-in votes that they probably should have been included on our list of songs to choose from. But by far the most popular write-in song was “You Should Be Here” by Cole Swindell.

A few others that were popular choices:

  • “The Father, My Son and the Holy Ghost” by Craig Morgan
  • “How Can I Help You Say Goodbye” – Patty Loveless
  • “Dad’s Old Number” – Cole Swindell
  • “Drink a Beer” – Luke Bryan
  • “Drowning” – Chris Young

Another song that was frequently mentioned was “Teddy Bear” by Red Sovine, the heartbreaking tale of a young boy who keeps himself company by talking to a trucker on his late father’s CB radio.

Actually there were so many good choices that it’s impossible to list them all here, everything from “Follow You To Virgie” by Tyler Childers to Hank Williams’ “Your Cheatin’ Heart” and “Broken Window Serenade” by Whiskey Myers.

But now, on to the winners.

The Top Five

In fifth, we had “Concrete Angel” by Martina McBride, which finished only a handful of votes behind Vince Gill’s “Go Rest High on That Mountain” in fourth.

In third place was the song that I honestly expected to win the whole thing: The George Jones classic, “He Stopped Loving Her Today.”

Your runner up was a song that never fails to bring tears to my eyes: “Alyssa Lies” by Jason Michael Carroll.

And in the top spot with 20% of the vote, the song that you the readers voted the saddest country song of all time…

“Whiskey Lullaby” by Brad Paisley and Alison Krauss.

So there you have it. I’ll be honest, I was a little surprised by the vote. And it wasn’t even particularly close when you considered that there were so many songs to choose from.

But that’s the great thing about sad country music: There ARE so many great songs to choose from.

Comments / 21


No one. I mean no one can touch his masterpiece….. he stop loving her today-The Possum. He lived in the same small city I lived in in the 80’s and 70’s off and on. He loved the Cajun culture and rich music Cajun ,country and zydeco

one o bob

the poll reflects the age group to a large degree. The old c&w songs are as sad as can be and beautiful in their simplicity. Hank sr. takes a backseat to no one when it comes to sad........and Patsy.

unclebuck 66

vern gosling, you don't know lonely until it's written in stone also a good one


Comments / 0