WHISKEY RIFF MADNESS 2024: ’90s Country Songs Starts NOW

Whiskey Riff Madness is BACK!

It’s that time of year again. March Madness is kicks off today with a full slate of games, and I’m just sitting back waiting for my bracket to be busted in the first round. (And hoping that none of the games are as terrible as that Virginia/Colorado State game was the other night…)

But March Madness isn’t the only tournament going on. For our annual Whiskey Riff Madness this year, we decided to throw it back to the ’90s once again, putting 64 of the best ’90s country songs up against each other to see which one comes out on top.

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

Our Methodology

The rules were simple: A song had to have been released in the ’90s, and it had to have been a top 40 hit. That’s about it.

Of course this left out some songs that ended up getting quite a few write-in votes. “Two Dozen Roses” by Shenandoah was released in 1989, so while it’s considered one of the all-time great ’90s songs, it actually wasn’t eligible. Same with “Killin’ Time” by Clint Black. And “It’s A Great Day To Be Alive” was released in 2000, so it wasn’t eligible either.

(And to whoever wrote in the “YYC BNA” by Paul Brandt, which was released in 2018, I’m not sure you understood the assignment).

But anyway…

From there, you guys voted on your favorite songs, and wrote in some of your own, to determine the seeding. We’re only including one song from each artist, which obviously eliminated a ton of good songs. “Neon Moon” made it as a #1 seed, so that means no “Boot Scootin’ Boogie” or “My Maria” from Brooks & Dunn. And George Strait could have easily had the entire bracket just to himself (in fact we did that a couple years ago), but the top vote-getter among his hits of the ’90s was “Carrying Your Love With Me,” so that’s the one that made it on there.

So if your favorite George Strait song isn’t on there, or you look at the bracket and think, “Why did this song make it over that one?” Well, that’s the song people voted for.

We tallied the votes, along with all the write-ins, and came up with the final seeding for our list of 64 songs, all based on your votes.

Did we have to leave out some great songs? Absolutely. Pretty much all of the songs from the ’90s are better than anything on the radio today, so just because a song isn’t on the list doesn’t mean it’s not a great song. It’s just impossible to include everything.

Hey, just like the NCAA tournament, a lot of deserving teams have to get left out. (Justice for Indiana State).

And that’s really it. We got the bracket built based on your votes, and now all that’s left is to start the tournament.

Here’s the final bracket:

And here’s a closer look at each region:

South:

East:

Midwest

West

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 Sunday, March 25.

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 it stay alive.