Should've Been a Cowboy

Riding Dreams: Toby Keith's Frontier Yearning
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Lyrics

I bet you've never heard ol' Marshal Dillon say

Expressing doubt that the listener has heard Marshal Dillon mention a desire for Miss Kitty to run away.

Miss Kitty, have you ever thought of runnin' away?

Asking Miss Kitty if she has ever considered settling down and marrying the speaker.

Settlin' down, would you marry me

Proposing marriage to Miss Kitty and asking if she would say yes if asked twice.

If I asked you twice and begged you, pretty please?

Expressing a plea for Miss Kitty to agree to marriage.

She'd have said, "Yes", in a New York minute

Speculating that Miss Kitty would have agreed quickly to marriage.

They never tied the knot, his heart wasn't in it

Explaining that Marshal Dillon and Miss Kitty never married because his heart wasn't fully committed.

He just stole a kiss as he rode away

Describing a stolen kiss as Marshal Dillon rode away.

He never hung his hat up at Kitty's place

Noting that Marshal Dillon never fully committed to a relationship with Miss Kitty.


I should've been a cowboy

Expressing a regret about not pursuing a cowboy lifestyle.

I should've learned to rope and ride

Regretting not learning cowboy skills like roping and riding.

Wearin' my six-shooter, ridin' my pony on a cattle drive

Imagining wearing a six-shooter and riding a pony on a cattle drive.

Stealin' the young girls' hearts

Fantasizing about stealing the hearts of young girls.

Just like Gene and Roy

Comparing oneself to iconic cowboys Gene and Roy.

Singin' those campfire songs

Imagining singing campfire songs in a cowboy lifestyle.

Woah, I should've been a cowboy

Reiterating the regret of not becoming a cowboy.


I might of had a sidekick with a funny name

Imagining having a humorous sidekick while engaging in wild activities.

Runnin' wild through the hills chasin' Jesse James

Envisioning chasing the notorious outlaw Jesse James.

Ending up on the brink of danger

Reflecting on the excitement and danger of the cowboy lifestyle.

Ridin' shotgun for the Texas Rangers

Imagining serving as a protector for the Texas Rangers.

Go west young man, haven't you been told?

Recalling the advice to go west for opportunities.

California's full of whiskey, women and gold

Highlighting California as a place of allure with whiskey, women, and gold.

Sleepin' out all night beneath the desert stars

Imagining sleeping under the desert stars.

With a dream in my eye and a prayer in my heart

Expressing a dream and a prayer for a fulfilling life.


I should've been a cowboy

Repeating the regret of not becoming a cowboy.

I should've learned to rope and ride

Reiterating the desire to learn cowboy skills.

Wearin' my six-shooter, ridin' my pony on a cattle drive

Imagining wearing a six-shooter and riding a pony on a cattle drive.

Stealin' the young girls' hearts

Fantasizing about stealing the hearts of young girls.

Just like Gene and Roy

Comparing oneself to iconic cowboys Gene and Roy.

Singin' those campfire songs

Imagining singing campfire songs in a cowboy lifestyle.

Woah, I should've been a cowboy

Reiterating the regret of not becoming a cowboy.


I should've been a cowboy

Repeating the regret of not becoming a cowboy.

I should've learned to rope and ride

Reiterating the desire to learn cowboy skills.

I'd be wearin' my six-shooter, ridin' my pony on a cattle drive

Imagining wearing a six-shooter and riding a pony on a cattle drive.

Stealin' the young girls' hearts

Fantasizing about stealing the hearts of young girls.

Just like Gene and Roy

Comparing oneself to iconic cowboys Gene and Roy.

Singin' those campfire songs

Imagining singing campfire songs in a cowboy lifestyle.

Woah, I should've been a cowboy

Reiterating the regret of not becoming a cowboy.


Yeah, I should've been a cowboy

Repeating the regret of not becoming a cowboy.

I should've been a cowboy

Final statement expressing the regret of not choosing a cowboy lifestyle.

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