The Best Covers of Toby Keith’s ‘Should’ve Been a Cowboy’

Both country music fans and artists alike were shaken when news broke of Toby Keith's passing on Feb. 5, 2024. The man was a pillar in the genre and left a legacy that extended beyond his music career.

Since his death, the world seems to have latched onto his 1993 hit "Should've Have Been a Cowboy" as his posthumous anthem. The song has served as both a remembrance of his life and a celebration of the mark he left on his fellow artists and fans.

Toby Keith's "Should've Have Been a Cowboy"

"Should've Have Been a Cowboy" was first recorded in 1992 and released as a single the following year. It was a solo write from Keith that appeared on his self-titled album. He said he was inspired to write the song after a real life experience in Dodge City, Kan.

“I think we were actually at the Long Branch Saloon or Miss Kitty’s Saloon — it was something to do with Gunsmoke,” Keith told Billboard in 2018. “This highway patrolman who I had met on the trip, his name was John, he jumps up. He was probably 45 or 50 back then, and he runs over to this 25-year-old cowgirl. He was going to show that he could bust a move. She turns him down. He comes over, and said, ‘She says she doesn’t dance.’ About 15 minutes later, a young cowboy comes in — and off they go on the dance floor. Everybody was making fun of him, and one of the guys said, ‘John, I guess you should have been a cowboy.’”

The moment sparked his creativity as he drew in elements of the television show Gunsmoke to aid in the imagery.

"I just started writing it, and it grew into Jesse James riding shotgun, and Gene and Roy," he continues. "It all happened in about 20 minutes.”

Toby Keith's Last Performance of "Should've Been a Cowboy"

Just a few months before his passing, Keith shared with Taste of Country that he was looking forward to pressing on with his music and even touring.

"So they've put this thing together, intricately, beat on it for six months. They've got a great plan together, and we built a new set, and we're getting the trucks and busses fired up. Our plan is to go forward, don't let this stuff define our future, let's go," he said at the time.

Keith played two shows in Las Vegas Dec. 10-11, which he said would serve as rehearsals for a 2024 tour. Unfortunately those shows would be his final performances.

Keep scrolling to see the best covers of Keith's iconic song "Should've Been a Cowboy."

Jess hosts the syndicated radio show, Taste of Country Weekend, which can be heard on country stations nationwide. Tune in for all of the best new country music, spotlights on new tracks and emerging artists, plus Double-Downs on all of your favorites. The weekend is always better with a little Taste of Country in it.