WHISKEY RIFF MADNESS 2021: ’90s Country Edition Championship Round Is LIVE


What a battle to reach the championship.

And no, I’m not just talking about that Gonzaga vs. UCLA game.

After almost 200,000 votes, we’ve finally reached the championship round of the 2021 edition of Whiskey Riff Madness. Each round has been an epic battle, and the Final Four was no different.

First we had Toby Keith’s “Should’ve Been a Cowboy” facing off with Alan Jackson’s “Chattahoochee.” AJ took a big lead to start out with, but “Should’ve Been a Cowboy” slowly chipped away at that lead throughout the day to give us a closer-than-expected matchup at the end.

Ultimately, though, “Chattahoochee” came out on top to give us our first song in the championship.

Unsurprisingly, the closest matchup of the day was between two powerhouse 90’s country songs (and artists): “Friends in Low Places” vs. “Check Yes or No.” I’ll be honest, I figured King George would run away with this one, but that wasn’t the case at all.

At the end of the day, “Check Yes or No” came away with the win by a mere 3% over “Friends in Low Places” to round out the final pairing.


So here we go. This is for all the marbles, and it’s a heavyweight match between two of the biggest names of 90’s country. “Check Yes or No” vs. “Chattahoochee.” George Strait vs. Alan Jackson.

Who’s going to come out on top? We’re about to find out.

Voting closes at 11:59 PM central time tonight. And we’ll be revealing the winner before the national championship game on Monday, so make sure to come back to see which song manages to take the title of Whiskey Riff Madness Champion.

A beer bottle on a dock



A beer bottle on a dock