The 6th Annual WHISKEY RIFF MADNESS Tournament: Sad Country Songs Edition

March Sadness

Whiskey Riff Madness is BACK!

It’s that time of year again: March Madness kicks off today, which means by the time you’re reading this my bracket is probably already busted. Oh well…

But March Madness isn’t the only tournament going on. For the sixth year in a row, we’re bringing you our annual Whiskey Riff Madness tournament.

And who doesn’t love sad country music? from good ole’ tear-in-your-beer heartbreakers to cheatin’ songs to tales of murder and everything in between, sad songs have always been a staple of country music. And let’s be honest, sad country songs just make me happy.

A couple of days ago, we asked you for some of your favorite country songs – and got a ton of great responses.

So for the 6th annual tournament, we decided to do a little March Sadness: We matched up some of the greatest sad country songs of all times and we’re puttin’ em head to head.

And as always, we’re letting you, our great Whiskey Riff readers, pick the winner.

Our Methodology

Because there are so many incredible sad country songs, we had to set some ground rules for this one.

First, we only included one song per artist (because if we didn’t make that rule then we would have just ended up with 64 George Jones songs…which might be a good idea for another bracket later on down the road, but that’s for another time).

But by limiting it to just one song, that means that we had to make some tough decisions on which songs to include. How do you decide between “Don’t Close Your Eyes” and “I’m Over You” by Keith Whitley? It’s a tough job but hey, somebody’s gotta do it.

We also wanted to make sure that all different types of country music were represented. So there are some classics, some newer mainstream country, some Texas country…a little bit of everything.

Did we have to leave some great songs out? Absolutely. But there were so many to choose from, and we had to narrow it down somehow. If your favorite song’s not on there, or if we didn’t choose the song that you think we should have from your favorite artist, it obviously doesn’t mean that we didn’t like it: It’s just impossible to include everything.

Hey, just like March Madness, a lot of deserving teams have to get left out.

The seeding was also damn near impossible, and was done pretty loosely based on a number of social media polls, with more of the classics pushing towards the higher seeds. If you disagree with our seeding…well, vote for your favorites anyway. Because that’s all that matters in the end.

And that’s really it. We got the songs narrowed down, got the bracket built, and now all that’s left is the voting.

The Final Bracket:

March Madness Bracket

And here’s a closer look at each region:


South Bracket


East Region


Midwest Region


West Region

So now it’s time for you to do your part.

Voting is open NOW for the Round of 64, and the first round ends at 11:59 PM central time on Saturday, March 18.

You can vote down below, or by clicking the link here, and you can vote as many times as you want if you have a favorite that you want to see move on to the next round.

And if last year’s tournament was any indication, some of these matchups are going to be CLOSE, so throw a few extra votes to your favorite song if you really want to see them stay alive.

VOTE NOW in the 2023 Whiskey Riff Madness: March Sadness Round of 64:

The Official Whiskey Riff March Sadness Playlist:


Apple Music

A beer bottle on a dock



A beer bottle on a dock