Riley Green’s Cover Of Toby Keith’s “Should’ve Been A Cowboy” Is So Damn Good

Riley Green country music

A perfect way to honor Toby Keith.

On Monday night, it was announced by his family that the country hitmaker passed away at the age of 62 after a long battle with stomach cancer:

“Toby Keith passed away peacefully last night on February 5th, surrounded by his family. He fought his fight with grace and courage. Please respect the privacy of his family at this time.”

And of course, tributes have been flowing in for the country legend. He made an impact on so many people through his music, but the stories about his character and the kind of man he was stand out to me above everything else.

I think we’ve all been taking a look back and reminiscing on all of the great music he brought us too, so much so that many of his albums have been charting on iTunes, including his 35 Biggest Hits is album, which has been sitting at the #1 spot for the last day or so.

And one current country star that’s been covering a Toby Keith hit for years now is Riley Green, who has kept “Should’ve Been a Cowboy” in his set list at pretty much every live concert he’s played going back quite some time. Written by Keith, the song was released in 1993 as his debut single from his self-titled debut album.

It eventually peaked at #1 on the U.S. Billboard Hot Country Songs, as well as reached #93 on the U.S. Billboard Hot 100 becoming a minor crossover hit.

Not a bad way to start what would become a legendary country music career…

Hearing Riley sing this as part of a medley that typically includes songs like “Dixieland Delight” and “Good Directions” is always one of my favorite parts of his show, and it will definitely hit a little bit different now knowing that Toby Keith is no longer with us.

I could seriously watch this all damn day (and no, not just because of the cowboy hat, though that doesn’t hurt but I digress…).

RIP Toby Keith, a country music legend.

“Should’ve Been A Cowboy”

A beer bottle on a dock



A beer bottle on a dock