Before it went platinum… before it blasted out of every jukebox in America… it was just a rough little song played for a friend.
Picture this: early ’90s, concrete hallway under the stadium lights in Texas. On one side, Troy Aikman, fresh off leading the Dallas Cowboys to Super Bowl glory. On the other, a tall guy in a white hat and a mullet, just a “new” singer from Oklahoma with a guitar in his hands.
Toby Keith starts to sing:
“I bet you never heard old Marshall Dillon say,
Miss Kitty have you ever thought of running away…”
That simple moment between friends turned into the most-played country song of the entire 1990s. Over 3 million radio spins. Number 1 on the charts. An anthem booming through Cowboys games all decade long. A song that followed people from pickup trucks to barrooms to stadium speakers for years.
But it all started in a quiet hallway, with one guitar and one future Hall of Fame quarterback leaning in, really listening.
The rough little song Toby played for his friend became a full-on studio classic, and that is exactly what you get in the official “Should’ve Been a Cowboy” music video. Here, the same young Toby from the early ’90s steps out of the tunnel and into the spotlight, backed by pedal steel, drums, and electric guitar instead of just an acoustic strum.
Toby Keith – Should’ve Been A Cowboy (Official Music Video)
And once you see how big “Should’ve Been a Cowboy” became, there is one last piece that ties the whole story together: how it was actually born. After the hallway performance and the polished music video, Toby sits down with Dan Rather and finally explains where the song came from, in his own words.