💬 Toby Keith and the 3-Billion Stream Plaque: Not Just Numbers — A Lifetime of Honest Music In a quiet backstage room, Toby Keith held a plaque from Pandora celebrating over 3 billion streams. An impressive number — but his eyes didn’t shine with excitement. They looked thoughtful, as if he were remembering those early days playing in tiny bars, mailing demo tapes to local radio stations. Three billion streams didn’t happen by luck. They’re the result of three decades of living and writing music with his whole heart. He sang about working folks, soldiers, and America — with a raw voice and an uncompromising spirit. And now, though his health has faded, there’s still something unmistakable in his gaze: Toby Keith never performed a persona. He simply lived — through every song.

Introduction

Toby Keith’s “Should’ve Been a Cowboy” isn’t just his debut single—it’s the song that sparked a storied career and became one of the most-played country songs of the 1990s. Released on February 12, 1993, it marked the beginning of his self-titled debut album under Mercury Records. Written and recorded by Keith himself, the track shot to No. 1 on both the U.S. Billboard Hot Country Songs and Canadian RPM Country Tracks charts in June of that year, and even crossed over to reach No. 93 on the Billboard Hot 100—a rare feat for a newcomer.

The genesis of the song is a classic Toby Keith story: during a hunting trip to Dodge City, Kansas, a friend named John tried—and comically failed—to dance with a cowgirl while still in his hunting gear. “John, you should’ve been a cowboy,” someone quipped—and a country classic was born. Keith later said he wrote the song in just twenty minutes while sitting in a motel bathroom .

Lyrically, the song is a love letter to the mythic American West, packed with nods to Gunsmoke characters like Marshall Dillon and Miss Kitty, legendary lawmen like Jesse James and the Texas Rangers, and classic singing cowboys Roy Rogers and Gene Autry . Keith’s energetic vocals, backed by crisp instrumentation, evoke wide-open landscapes and nostalgic longing for freedom and adventure .

More than three decades later, “Should’ve Been a Cowboy” endures as Keith’s signature anthem. It became the most-played country song of the 1990s and has been certified triple-platinum. It was so beloved that in 2018, the original album was reissued as Should’ve Been a Cowboy (25th Anniversary Edition) .

This 300‑word introduction captures the song’s lightning‑strike creation, chart domination, and its deep roots in cowboy lore—setting the stage for a deeper dive into its cultural impact and Toby Keith’s legacy.

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Lyrics

I bet you’ve never heard ol’ Marshal Dillon say
Miss Kitty, have you ever thought of runnin’ away?
Settlin’ down, would you marry me
If I asked you twice and begged you, pretty please?
She’d have said, “Yes”, in a New York minute
They never tied the knot, his heart wasn’t in it
He just stole a kiss as he rode away
He never hung his hat up at Kitty’s place
I should’ve been a cowboy
I should’ve learned to rope and ride
Wearin’ my six-shooter, ridin’ my pony on a cattle drive
Stealin’ the young girls’ hearts
Just like Gene and Roy
Singin’ those campfire songs
Woah, I should’ve been a cowboy
I might of had a sidekick with a funny name
Runnin’ wild through the hills chasin’ Jesse James
Ending up on the brink of danger
Ridin’ shotgun for the Texas Rangers
Go west young man, haven’t you been told?
California’s full of whiskey, women and gold
Sleepin’ out all night beneath the desert stars
With a dream in my eye and a prayer in my heart
I should’ve been a cowboy
I should’ve learned to rope and ride
Wearin’ my six-shooter, ridin’ my pony on a cattle drive
Stealin’ the young girls’ hearts
Just like Gene and Roy
Singin’ those campfire songs
Woah, I should’ve been a cowboy
I should’ve been a cowboy
I should’ve learned to rope and ride
I’d be wearin’ my six-shooter, ridin’ my pony on a cattle drive
Stealin’ the young girls’ hearts
Just like Gene and Roy
Singin’ those campfire songs
Woah, I should’ve been a cowboy
Yeah, I should’ve been a cowboy
I should’ve been a cowboy