WHISKEY RIFF MADNESS: ’90s Country Round Of 32 Voting Opens NOW

90s country
Whiskey Riff

The first round is in the books.

It’s March Madness, so this year for our annual Whiskey Riff Madness tournament we decided to take it back to the ’90s. We paired up 64 all-time great ’90s 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 from the opening contests.

We had the biggest opening round we’ve EVER had for our annual Whiskey Riff Madness tournament, with over 118,000 total votes cast. And all of the #1-seeds sailed through easily, but by far the biggest blowout of the first round came from Toby Keith and “Should’ve Been A Cowboy,” which racked up 97% of the vote against Lee Roy Parnell’s “What Kind Of Fool Do You Think I Am.” A lot of people are saying that Toby’s going to be impossible to beat this year, and after his first round performance, it’s hard to argue with that.

But despite the blowouts from the top seeds, we had a ton of close matchups throughout the rest of the bracket. Vince Gill and Martina McBride were locked in an intense back-and-forth battle, but ultimately “Independence Day” came out on top, narrowly beating out “Go Rest High On That Mountain.” And two underrated classics in “I’d Be Better Off (In a Pine Box)” and “Goodbye Says It All” were separated by only a handful of votes at the end of the day, with Doug Stone’s heartbreaker moving on to the next round over the BlackHawk hit.

The biggest upset, though, and maybe one of the biggest surprises I’ve seen in all of our tournaments, was the Dixie Chicks taking down George Jones, with “Cowboy Take Me Away” knocking out “Choices” by a 56-44 margin to stay alive.


But now it’s time for round 2.

Here’s the bracket for the Round of 32:

And a closer look at the individual regions:



March Madness




You have until 11:59 PM CDT on Wednesday, March 27 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.

And if you need some inspiration while you vote, check out our Saved By ’90s Country playlist on Spotify and Apple Music.


Apple Music

Click here to shop the 90’s Country Collection in the Whiskey Riff Shop.


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