MARCH SADNESS: Sad Country Songs Round Of 32 Voting Is LIVE

March Sadness

Round one is in the books, and we saw a shocking 16-seed upset over a 1-seed.

No, I’m not talking about Fairleigh Dickinson’s insane win over Purdue. I’m talking about our 6th Annual Whiskey Riff Madness tournament – or as we’re calling this one, March Sadness.

We paired up 64 all-time great country songs and let you, the readers, vote for your favorites. And now we’re down to 32.

But before we get into the next round, let’s take a look back at some of the matchups.

We saw more close votes than we’ve ever seen in any of our tournaments. But there were still a few blowouts, like the #1 overall seed “He Stopped Loving Her Today” absolutely dominating its matchup against Kathy Mattea’s “Where’ve You Been” with a whopping 97% of the vote.

Hank Williams Jr.’s “Weatherman” also put on a strong showing in the first round, easily coming out on top of “She’s Using” by Kaitlin Butts. And Tim McGraw’s “Don’t Take the Girl” got the second highest number of votes in the first round, beating Kylie Rae Harris’ heartbreaker “Twenty Years From Now.”

Only three other songs managed to crack 90% of the vote: “Three Wooden Crosses” by Randy Travis, Keith Whitley’s classic “Don’t Close Your Eyes,” and the haunting “Whiskey Lullaby” by Brad Paisley and Alison Krauss.

Those were the blowouts. But there were quite a few more that were separated by only a handful of votes.

After a back and forth matchup over the past couple days, Steve Wariner’s “Holes in the Floor of Heaven” managed to inch by John Prine’s “Sam Stone” at the last minute and sneak into the next round. And “Billy Stay” by Zach Bryan just barely edged out Justin Moore’s “If Heaven Wasn’t So Far Away” to stay alive.

One of the closest battles of the round was between “Almost Home” by Craig Morgan and “David” by Cody Jinks – but at the end of the day, Craig Morgan got just enough votes to move on to the round of 32.

But by far the closest matchup of the round came from Miranda Lambert’s “Over You” going up against “The Little Girl” by John Michael Montgomery. And by only a handful of votes, “Over You” managed to pull off the win.

There were a few surprising upsets along the way too. “She Thinks His Name Was John” never really stood a chance against “Travelin’ Soldier,” and while I’m not sure it’s ever fair to call Chris Stapleton an underdog (no pun intended), “Maggie’s Song” took down the classic hit “Crazy” by Patsy Cline.

Vince Gill’s tearjerker “Go Rest High On That Mountain” was another surprising early loss, but it faced a tough matchup against “Follow You To Virgie” by Tyler Childers. And a song that got a lot of discussion in the comments, “Alyssa Lies” by Jason Michael Carroll, couldn’t manage to take down “Lead Me Home” by Jamey Johnson, and ultimately made an early exit from the tournament.

But by far the biggest upset came from the 16-seed “I Wish Grandpas Never Died” by Riley Green taking down the iconic Dolly Parton hit and #1 seed “I Will Always Love You.”

So that’s the first round. But now it’s time to do it all over again.

Here’s the bracket for the Round of 32:

March Madness

And now it’s time to vote.

You have until 11:59 PM CDT on Tuesday, March 21 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.

VOTE NOW in the 2023 Whiskey Riff Madness: March Sadness Round of 32:

The Official Whiskey Riff March Sadness Playlist:


Apple Music

A beer bottle on a dock



A beer bottle on a dock