And The WHISKEY RIFF MADNESS: ’90s Country Songs Winner Is…

Whiskey Riff

And the winner is…

Whiskey Riff Madness 2024 is officially in the books. For our annual tournament, this year we threw it back to the ’90s and put 64 of your favorite ’90s country songs head to head to see which one would come out on top.

And for our championship round, just like in the NCAA Tournament, we had two #1 seeds going head to head.

Toby Keith and “Should’ve Been A Cowboy” have looked like the favorites all tournament, easily crushing any competition it faced in what may have been a sentimental run to the championship just two months after the legendary country icon’s passing.

But in the championship, “Should’ve Been A Cowboy” had to face off with another powerhouse: Alan Jackson’s “Chattahoochee,” which actually won the tournament a few years ago when we first did ’90s Country Madness.

So who came out on top?

Well, after hundreds of thousands of votes and plenty of debate, the winner is…

“Should’ve Been A Cowboy” – Toby Keith

That’s right: After spending the entire tournament as the sentimental favorite, Toby Keith and “Should’ve Been A Cowboy” pulled out the win with nearly 65% of the vote over “Chattahoochee.”

And while it was a popular win, it wasn’t an easy one: Along the way, “Should’ve Been A Cowboy” took out favorites like “She’s In Love With The Boy,” “Time Marches On, “Friends In Low Places,” and even the Brooks & Dunn classic “Neon Moon.”

Not an easy path to victory – but one that was meant to be this year.

Here’s the final bracket:

So congrats on a well-earned victory to Toby Keith in our 2024 Whiskey Riff Madness tournament.

And of course, crack one open, pour it into a red Solo cub, and turn this one up in his honor:

A beer bottle on a dock



A beer bottle on a dock