But like… what else could it have been? It’s iconic. Toby Keith left a legendary mark on country music, and he came out of the gate swinging with his first hit “Should’ve Been A Cowboy.” And on this date in 1993, he released the song that started it all, his debut single, which was included on his self-titled debut album. The 4x Platinum song peaked at #1 on the U.S. Billboard Hot Country Song chart. The song has more than three million spins on country radio too, which makes it the most-played country song of the 1990s (and rightfully so). Yeah, it’s true… the first song he ever put out became the most-played song on country radio in the ’90s, which was a golden era of country and produced so many classics like “Friends in Low Places,” “Any Man of Mine” and “Boot Scootin’ Boogie,” just to name a few. That’s no easy feat, and calling it impressive doesn’t feel like anywhere close to the description that really deserves. In an interview with Billboard in 2018, Keith shared a little bit of inspiration behind the song, which is an incredible story too: “I think we were actually at the Long Branch Saloon or Miss Kitty’s Saloon — it was something to do with Gunsmoke. 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.’” But the rejection – and the line from his friend – got the wheels turning, and Toby got to writing what would become his signature song. And as it turns out, once he started writing, it didn’t take long to get the whole song done: “I thought, ‘I betcha never heard Marshal Dillon have any woman problems because Miss Kitty was always knocking his back door down.’ I just started writing it, and it grew into Jesse James riding shotgun, and Gene and Roy. It all happened in about 20 minutes.” Classic… and the rest was history. It’s amazing to think that Keith came out of the gate swinging with a song like this, and he’d follow it up with an impressive 20 #1 hits throughout his career. The song, which he wrote by himself, launched his career, and to this day, is probably his most beloved. North Carolina alt country band, American Aquarium, covered the song on their 2021 album Slappers, Bangers, and Certified Twangers: Vol 1. And because of this song, and so many other legendary hits, Keith, along with fellow Country Music Hall of Famer, Kenny Rogers, and Academy Award-nominated actor, Ed Harris, will be inducted into the museum’s Hall of Great Western Performers and Hall of Great Westerners. With the induction, Keith and Rogers will join fellow country legends such as George Strait, Bob Wills, Vince Gill, Reba McEntire and Brooks & Dunn. As for Harris, he’ll join the likes of Burt Reynolds, Sam Elliot, Kurt Russell and many more as members of the Hall of Fame. The “American Soldier” singer’s daughter, Krystal Keith, would express just how grateful she is for her father to be recognized by the museum, noting how the honor reflected the values and life Keith lived. “This honor reflects the life my dad lived and the values he stood for. We’re grateful to the National Country & Western Heritage Museum for recognizing his place in the history and how his career served and celebrated the heritage of the country and Western way of life.” It’s incredibly well-deserved, and it all started with this heater… gonna continue to spin this one today, and here’s to the great Toby Keith. “Should’ve Been A Cowboy” The post The Most-Played Country Song Of The ’90s Wasn’t Garth Brooks Or George Strait… It Was Toby Keith’s Debut Single first appeared on Whiskey Riff.