Before it became the biggest country hit of the ’90s, before stadium speakers and tailgates and red Solo cups, “Should’ve Been a Cowboy” was just a brand-new song in Toby Keith’s living room.
Toby on guitar and his buddy Troy Aikman on the couch, listening. Troy was not a random fan. He was the first person to ever hear the song all the way through. One friend, one room, one take. That is the real “birth moment” of the anthem the whole world would soon play on repeat.
If you only know the song from radio or bar jukeboxes, you have missed that first run-through. The living-room clip shows Toby before the fame around this song, just a young songwriter trying out a wild idea on a Super Bowl quarterback friend.
Toby’s Song Before It Was a Hit
Then you can jump to what that little living-room jam grew into. The official music video for “Should’ve Been a Cowboy” is the same Toby, now under real lights, with a full band and a crowd. It is the sound of that private moment turning into a country soundtrack for an entire decade.
Toby Keith – Should’ve Been A Cowboy (Official Music Video)
And to really close the loop, Toby later sat down with Dan Rather and told the story himself. In this interview, he explains how he wrote it, how fast it took off, and how that simple idea from home turned into a career-defining song.