March Sadness

And with that, March Madness has come to an end…and so has March Sadness.

For our 6th Annual Whiskey Riff Madness tournament, we paired up 64 all-time great sad country songs and let you, the readers, vote for your favorites.

But before we get to the winner, let’s take a look back at how we got here.

We had some close matchups, some blowouts – and every single round of the tournament had more votes cast than the previous round as people rallied behind their favorite sad country songs.

And ultimately it came down to just two: the classic “He Stopped Loving Her Today” by George Jones vs. the Whiskey Myers hit “Broken Window Serenade.”

“He Stopped Loving Her Today” came into the tournament as the top overall seed, and absolutely dominated the early rounds, taking down Kathy Mattea’s “Where’ve You Been,” Johnny Paycheck’s “Old Violin” and “Maggie’s Song” by Chris Stapleton.

The Possum faced his first real test going up against “Don’t Close Your Eyes” by Keith Whitley, but ultimately made it to the Final Four to face off against another #1-seed, “Whiskey Lullaby” from Brad Paisley and Alison Krauss.

Whiskey Myers started as a #5-seed with “Broken Window Serenade,” and took down Carrie Underwood’s “Temporary Home” and “Remember When” by Alan Jackson before really catching fire and knocking off heavy hitters like “I’m So Lonesome I Could Cry” by Hank Williams and Johnny Cash’s cover of “Hurt.”

Finally, they managed to take down Garth Brooks and “The Dance” for a chance to compete for the big trophy. (Just kidding, there’s no trophy).

So after 63 matchups and hundreds of thousands of votes cast, who did you choose as the winner?

“Broken Window Serenade” Whiskey Myers

For the second year in a row, Whiskey Myers fans put together an absolutely dominating run for their guys, this year pushing “Broken Window Serenade” to the top of a STACKED field of the greatest sad country songs ever made.

Ultimately, “Broken Window Serenade” came out on top in the final round with 65% of the vote over what was thought to be the heavy favorite to win it all.

And that, as they say, is why you play the game.

Overall we’ve had a ton of fun with this one, reading all the comments and watching the votes roll in over the past couple weeks. And once again, shoutout to all the Whiskey Myers fans out there, because that was quite the impressive run against some pretty tough matchups. Y’all made yourselves heard in a big way.

Here’s the final bracket:


So pour a drink and listen to your 2023 March Sadness winner – and if you get a few tears in your beer, that’s ok too.

The Official Whiskey Riff March Sadness Playlist:


Apple Music

A beer bottle on a dock



A beer bottle on a dock