Should've Been A Cowboy
Toby Keith Lyrics

I bet you've never heard ol' Marshal Dillon say
Have you ever heard of Matt Dillon, the central character in the long-running TV series ‘Gunsmoke’? Here, Toby Keith imagines a conversation between Matt and Miss Kitty. He wonders if Matt has ever asked Kitty to run away with him and get married.

Miss Kitty, have you ever thought of runnin' away?
Toby Keith imagines that Matt Dillon asked Miss Kitty if she has ever considered running away with him.

Settlin' down would you marry me?
Matt probably asked Kitty if she wanted to settle down and marry him.

If I asked you twice and begged you pretty please?
Toby Keith imagines that Matt asked Kitty to marry him even after she said no the first time, and he begged her pretty please to say yes.

She'd have said 'Yes' in a New York minute
Toby Keith imagines that Miss Kitty would have said yes to Matt's proposal almost instantly.

They never tied the knot, his heart wasn't in it
Despite Miss Kitty's willingness, the two of them never got married. Toby Keith suggests that it might be because Matt's heart wasn't truly in it.

He just stole a kiss as he rode away
When Matt didn't want to get married, he just stole a kiss from Miss Kitty before he rode away.

He never hung his hat up at Kitty's place
Despite their relationship, Matt never decided to stay and live with Miss Kitty.

I should've been a cowboy
Toby Keith laments that he should have been a cowboy instead of living an ordinary life.

I should've learned to rope and ride
Toby Keith wishes that he had learned to ride horses and lasso cows as a cowboy.

Wearin' my six-shooter, ridin' my pony on a cattle drive
The image of a cowboy wearing six-shooters and riding his horse in a cattle drive is a romantic, idealized vision of the cowboy life that Toby Keith wishes he could have experienced.

Stealin' the young girls' hearts, just like Gene and Roy
Cowboy actors Gene Autry and Roy Rogers were popular in the mid-20th century. Toby Keith wishes that he could have been admired like them and stolen the hearts of young girls.

Singin' those campfire songs
The campfire songs are a reference to the music that cowboys used to sing while sitting around the campfire. Toby Keith wishes he could have been a part of that.

Woah, I should've been a cowboy
Toby Keith emphasizes that he really, really regrets not having been a cowboy.

I might of had a sidekick with a funny name
Toby Keith imagines having a humorous cowboy sidekick with an unusual name.

Running wild through the hills chasin' Jesse James
Toby Keith imagines that he could have had a thrilling life as a cowboy, running after the infamous outlaw Jesse James.

Ending up on the brink of danger
Living the cowboy life would have meant being on the edge of danger for Toby Keith, which he may have found exciting.

Ridin' shotgun for the Texas Rangers
Toby Keith imagines himself becoming a law enforcement official and riding shotgun with the Texas Rangers.

Go West young man, haven't you been told?
This line alludes to the famous advice given to young people to go west and explore the frontier. Toby Keith is regretful to have missed out on that opportunity.

California's full of whiskey, women, and gold
Toby Keith imagines the west coast of the USA as being full of adventure and riches, something that he could have discovered if he had been a cowboy.

Sleepin' out all night beneath the desert stars
Living in the wild outdoors, sleeping beneath the stars, is something that Toby Keith romanticizes and wishes he could have experienced as a cowboy.

With a dream in my eye and a prayer in my heart
Toby Keith expresses the idea that he would have embarked on his cowboy journey with his eyes fixed on a dream and a prayer in his heart for success.