Do you believe in miracles? Colby Acuff sure does.
The first round of Whiskey Riff Madness 2026 wrapped up this past weekend, and it was easily the wildest round we’ve had since we started doing the tournament a decade ago. This year, we took 64 country artists from every corner of genre (mainstream to red dirt to Appalachia… truly covering all bases) and let the fans vote on their favorites.
When it came to seeding the tournament, that was based on monthly Spotify listeners. The most objective way to seed the artists, but also… the most surprising. Some of seeds were truly shocking, but don’t blame us for how we did the seeding., take it up with music fans who listen through Spotify. And just as the actual March Madness tournament often plays out, a lot of the favorites came through victorious in the first round.
But we also had a number of exciting and unexpected upsets.
No. 12-seed Cody Jinks never gave No. 5-seed Carrie Underwood a chance, and a No. 13-seeded Sturgill Simpson pulled off a win over No. 4-seed Jon Pardi. We also saw Jason Aldean go down against the No. 14-seed Turnpike Troubadours, and a No. 10-seed Colter Wall won comfortably over No. 7-seed Tucker Wetmore. Looks like the indie artists came to play this year.
As you can see, there were plenty of underdogs that made it to the second round… and the biggest underdog of them all was No. 16-seed Colby Acuff.
Simply put, Acuff pulled off the biggest upset that Whiskey Riff Madness has ever seen. He was matched up against No. 1- seed Chris Stapleton in the first round, and he was down early to the “White Horse” singer. Going into the weekend, Stapleton actually had 75% of the vote in this matchup.
But Colby Acuff didn’t hear no bell, and he rallied his dedicated fans to mount a comeback for the ages, even having a t-shirt made for the matchup:
At the time of that tweet, Colby needed around 1,000 votes to catch Stapleton. But he never gave up, and neither did his fans. Slowly but surely, the Idaho native got enough votes to win his first round matchup and claim the title for biggest upset in the history of Whiskey Riff Madness with 59% of the votes by the end of the round.
@colby_acuff The greatest story ever told. #marchmadness #march #kingofthehill #countrymusic ♬ original sound – Colby Acuff
That meme, and the many others that have been posted by Colby Acuff, helped him take down Thanos Chris Stapleton.
And to be clear, Acuff isn’t satisfied with a first round win. He wants to win the whole damn thing. The “If I Were The Devil” singer graciously worked out some time in his schedule to talk to us here at Whiskey Riff about his upset, his preparation for his second round matchup against Dierks Bentley, and how his new song – “White Flag” – perfectly encapsulates the spirit of his current Cinderella run in Whiskey Riff Madness.
First off, how does it feel to make history and knock off a No. 1 seed as a No. 16 seed in the tournament?
“I think, more than me winning, it was really just a fun way to interact with the fans. Everyone who knows me understands that we’re always considered the ‘underrated’ artist, which really just means ‘undiscovered.’ And instead of pushing against that, I’ve always embraced it.
I love being the underdog. You can’t choose when you are celebrated, but you can choose how you are celebrated. And if my fans want to celebrate by winning a March Madness bracket with the use of memes, then put it on my headstone. It’s pretty incredible what people can do.”
Obviously, Chris Stapleton is one of the greats. I’m sure there’s a lot of joy in pulling off the upset, but you also have to tip your cap to Chris, do you not?
“Chris Stapleton is on a short list for the most talented person on earth. Not to mention he is extremely kind and grounded. Him being so perfect is half the reason this worked. He was the unthinkable match.
Stapleton is a hero of mine, and I truly don’t think he ever knew this was going on, nor do I think he cares, which makes him even more of a hero to me. At the end of the day he is an absolute legend.”
If we’ve learned anything from this past week, it’s to believe in miracles, and to believe in memes. How did you land on this meme movement, and why do you think it worked?
“Miracles happen in very mysterious ways. I’m just having fun with it at this point.”
Once you found out that you pulled off the impossible, toppling a giant like Stapleton in the first round, how did you celebrate? Who did you call, if anyone?
“I woke up in a hotel in Kansas City, got in the Van, and made more memes. I hope we upset our way to a championship.”
Now you’ve got a tough second round matchup against No. 9-seed Dierks Bentley. He pulled off an upset of his own in the first round – albeit a minor one. What gives you the confidence that you’ll continue to move on in Whiskey Riff’s Country Music Madness?
“We just gotta hit our shots on offense, and get back on defense. Bentley is a good team, I watched the tape back from his last game. It’s going to be tough to stop him in the key, but I believe in our boys to bring it home.”
Is there any fear that the clock is going to strike midnight on your Cinderella story?
“I’ve never feared death.”
What’s one song of yours – or of someone else’s – that you feel captures the spirit of this March Madness run that you are making? “Runnin’ Down A Dream” by Tom Petty is one that comes to mind for me.
“What’s so funny is that my newest single ‘WHITE FLAG’ is about never giving up. It really played in so well for this situation. I guess sometimes things are just meant to be.”
What would a Whiskey Riff Madness championship mean to you?
“It would mean what I already know. I have the best fans in the world.”
To help Colby Acuff continue to move on in the tournament, or to vote for other favorite country music artists of yours, you can vote at the link HERE. Voting in this round ends on Wednesday, March 25 at 11:59 pm central time, and you can vote as many times as you’d like. So rally the fanbases for your favorite artists, because as we saw in the first round, truly anything is possible.
Oh, and here’s Colby’s anthem for his Cinderella run, in case you haven’t heard it:
“WHITE FLAG” by Colby Acuff
