MARCH SADNESS: Sad Country Songs Sweet Sixteen Voting Is LIVE

March Madness

Another round down – and this one had some upsets.

For our 6th Annual Whiskey Riff Madness tournament – or as we’re calling this one, March Sadness, we paired up 64 all-time great sad country songs and let you, the readers, vote for your favorites.

One thing we’ve heard over and over is how tough it is to choose between some of these songs, and it shows in the voting. So let’s take a look at the results from the Round of 32.

There were only a handful of matchups that weren’t even close this time around. “He Stopped Loving Her Today” blew by Johnny Paycheck’s heartbreaker “Old Violin” with 94% of the vote, and is a heavy favorite to win the whole thing at this point. But “Blue Eyes Crying in the Rain” also made easy work of Benjamin Tod’s “Using Again,” and “Whiskey Lullaby” by Brad Paisley and Alison Krauss also continues to dominate, easily taking down Luke Combs’ “Even Though I’m Leaving,” which means that some of these heavy hitters are on a collision course with each other in these upcoming rounds.

A couple of my all-time favorite sad country songs also got knocked out this round, with Doug Stone’s “I’d Be Better Off (In a Pine Box)” getting a tough draw and going down to Hank Williams’ classic “I’m So Lonesome I Could Cry,” and Steve Wariner’s “Holes In the Floor of Heaven” losing to Zach Bryan’s “Billy Stay.” Just some tough matchups for some all-time great songs.

In another surprising upset, this round also saw “Follow You to Virgie” by Tyler Childers edge out “That’s My Job” by Conway Twitty. The biggest upset though, came from Whiskey Myers, who had an incredible comeback after being down 10% on the final day of voting to take down Alan Jackson’s “Remember When” with 58% of the vote.

Craig Morgan’s “Almost Home” also put up a tough fight against #16 seed “I Wish Grandpas Never Died,” but ultimately Riley Green’s Cinderella run rolls on.

But the closest matchup of the round came from Chris Stapleton’s “Maggie’s Song” versus “Travelin’ Soldier.” At the end of the day, Stapleton managed to pull of the win with a razor-thin lead of only 50.8%. Just proof that every vote counts…

So now we’re down to the Sweet Sixteen. Can “Broken Window Serenade” pull off another incredible upset over Hank Williams? Will “He Stopped Loving Her Today” continue to dominate against a modern-day powerhouse like Chris Stapleton?

And how in the hell am I supposed to choose between “Weatherman” and “Don’t Close Your Eyes?”

I guess we’ll find out – because voting in the Sweet Sixteen is open now.

Here’s the updated bracket:

March Madness bracket


March Madness bracket



March Madness bracket


March Madness bracket


March Madness bracket

You have until 11:59 PM CDT on Friday, March 24 to get your votes in, and as always you can vote as many times as you want either down below or by clicking the link here.

If you have a favorite song you want to win, it’s probably a good idea to throw them a few extra votes. As we saw in the last round, every vote matters.

The Official Whiskey Riff March Sadness Playlist:


Apple Music

A beer bottle on a dock



A beer bottle on a dock