Flatland Cavalry & Colby Acuff Honor Toby Keith With “Should’ve Been A Cowboy”

Flatland Cavalry and Colby Acuff Country music
Taylor Hendrix

Raise a solo cup for the Big Dog Daddy.

Everyone has been tipping their hat to the late Toby Keith. I think I speak for the collective when I say that since the passing of Toby Keith, he has been blaring through speakers everywhere. Whether you are listening to a cover of his songs or straight from his discography, the trend is all Toby Keith all day long. From the patriotic anthems to the slow love ballads, they all hit.

Flatland Cavalry recently had a milestone career moment. While on stage, they brought out their friend and supporting act, Colby Acuff, to tip their hats to the Oklahoma native.

Flatland had covered “Should’ve Been A Cowboy” at their show right after the news broke that Toby Keith had peacefully passed at 62 while in Athens, Georiga.

@whiskeyriff Tipping their hat to the great Toby Keith. // 🎥: @kurtholtzclaw617 #whiskeyriff #countrymusic #tobykeith #flatlandcavalry ♬ original sound – Whiskey Riff

They kept the track running during one while they graced the historic Ryman Auditorium stage for their debut over the weekend. The venue is filled with country music history and is a stage Keith had graded many times, with one of his last performances there being in September 2023.

@jennymcyall @Toby Keith’s last performance at The Ryman Auditorium September 26, 2023. He sounded amazing! So grateful we got to see him just 4 1/2 months before he passed away. 💔 #fyp #foryou #fypシ ♬ original sound – Jenny McClain

Flatland and Colby Acuff made sure that the Ryman felt Keith’s soul that night as they belted out the words to “Should’ve Been A Cowboy” once again. The Texas boys sound spot on with the addition of Acuff’s Idahoan twang. These two artists show that Keith’s music touched all parts of the United States and beyond.

Cleto’s energy on stage as he bops to the melody with Acuff just makes you smile. Toby Keith’s music brought everyone together, still does, and always will.

I think this should be a permanent addition to Flatland’s setlist. Talk about that electric last note! By the end of watching this video, you will be doing the same lasso motion Cleto does to get the crowd going.

A beer bottle on a dock



A beer bottle on a dock