Should’ve Been A Cowboy

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Should’ve Been A Cowboy

performed by Toby Keith
written by Toby Keith
released on February 12, 1993

I bet you’ve never heard old Marshal Dillon say
Miss Kitty have you ever thought of running away
Settling down would you marry me
If I ask you twice and beg you pretty please
She’d’ve said, “Yes” in a New York minute
They never tied the knot
His heart wasn’t in it
He 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
Wearing my six-shooter riding my pony on a cattle drive
Stealing the young girls’ hearts
Just like Gene and Roy
Singing those campfire songs
I should’ve been a cowboy

I might have had a sidekick with a funny name
Running wild through the hills chasing Jesse James
Ending up on the brink of danger
Riding shotgun for the Texas Rangers

Go west young man, haven’t you been told
California’s full of whiskey, women and gold
Sleeping 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
Wearing my six-shooter riding my pony on a cattle drive
Stealing the young girls’ hearts
Just like Gene and Roy
Singing those campfire songs
I should’ve been a cowboy

I should’ve been a cowboy
I should’ve learned to rope and ride
Wearing my six-shooter riding my pony on a cattle drive
Stealing the young girls’ hearts
Just like Gene and Roy
Singing those campfire songs
I should’ve been a cowboy
I should’ve been a cowboy
I should’ve been a cowboy
I should’ve been a cowboy

______________________________

I thought of this song recently as the my regional peers honored the anniversary of the passing of Toby Keith. Should’ve Been a Cowboy is the song that launched him to stardom. TK’s life and career pushed over a lot of other historical dominoes, (perhaps most notable among them the discovery and signing of a young Taylor Swift.)

Who knows? Without Should’ve Been a Cowboy, maybe Taylor Swift is still an obscure songwriter living n Nashville.

(more on the song, via wiki)

“Should’ve Been a Cowboy” is a song written and recorded by American country music artist Toby Keith. It was released on February 12, 1993, as his debut single and the first from his self-titled debut album. On June 5, 1993, the song reached number one on the US Billboard Hot Country Songs and the Canadian RPM Country Tracks charts. It also peaked at number 93 on the Billboard Hot 100, making it a minor crossover hit.

The song is a staple following sporting events at Oklahoma State University (home of the Cowboys), often played over the venue’s PA system several times in succession as fans emptied the stadium or arena.

American Aquarium covered the song on their 2021 album Slappers, Bangers, and Certified Twangers: Vol 1.

Content

The song was inspired by an incident Keith experienced at a bar in the early 90s. According to Keith:

“This highway patrolman who I had met on the trip, his name was John, he jumps up. He was probably 45 or 50 back then, and he runs over to this 25-year-old cowgirl. He was going to show that he could bust a move. She turns him down. He comes over, and said, ‘She says she doesn’t dance.’ About 15 minutes later, a young cowboy comes in — and off they go on the dance floor. Everybody was making fun of him, and one of the guys said, ‘John, I guess you should have been a cowboy.’ ” 

The lyrics romanticize the cowboy lifestyle through references to old Westerns. The first verse references Gunsmoke, in which cowboy hero Marshal Dillon never settled down with his love interest Miss Kitty. The second verse tells of his own adventures if the narrator were a cowboy: having “a sidekick with a funny name” (possibly a reference to sidekicks like Tonto or Gordito), travelling west to California (including the historical quote “Go West, young man“), hunting down Western outlaw Jesse James, joining up with the Texas Rangers, and so on. The chorus refers to famous singing cowboys Gene Autry and Roy Rogers, and lists common patterns depicted in Westerns such as six-shooters (revolvers) and cattle drives.

Chart positions

“Should’ve Been a Cowboy” debuted at number 69 on the Hot Country Songs chart for the week of March 6, 1993. It became Keith’s first number one single on the chart dated June 5, 1993, remaining there for two weeks. It was certified three-times platinum by the RIAA on September 18, 2023, thirty years after its release. Following Keith’s death on February 5, 2024, the single re-entered the Hot Country Songs chart at number 12 on the chart week dated February 17, 2024. It was one of five Toby Keith songs to re-enter the chart that week, as well as the highest peaking.

Chart (1993)	Peak position
Canada Country Tracks (RPM)	1
US Billboard Hot 100	93
US Hot Country Songs (Billboard)	1

TK spent the better part of 30 years writing enough hit songs to land himself in the country music and songwriter Halls of Fame. He also leveraged his fame and fortune to establish pediatric cancer philanthropies:

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In 2004, Keith helped found Ally’s House, a cancer charity named after Allison Webb, the deceased daughter of one of Keith’s former bandmates. Webb died a month before her third birthday to Wilms’ tumor.

This is a special charity to me. I saw firsthand how a child’s cancer diagnosis can devastate a family. Please join me in supporting these kids through Ally’s House. We’re gonna make it better for the kids.

In 2006, he established the Toby Keith Foundation to build housing for pediatric cancer patients and their families. In late 2013, the foundation built the OK Kids Korral, a place for child OU Medical Center cancer patients to live in. Over two decades since its creation, the annual Toby Keith & Friends Golf Classic has raised more than $15 million for the OK Kids Korral. He described it to The Oklahoman in 2019 as his greatest accomplishment.

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So for the above reasons, his love of the Oklahoma Sooners, and his restaurant chain, “I Love This Bar & Grill”, the late Toby Keith was and is something of a local legend in the state of Oklahoma. I know and have talked with a few people who met him personally (he essentially never left Oklahoma for Nashville, even at the height of his popularity, and he was out and about enough that those encounters were common). I have never heard anyone share a bad experience with him. By all accounts, he was a really good dude.

In addition to all of the above, the song also resonates with me for personal reasons. It was released in early 1993, just a few weeks after I and my family moved from an extremely rural ranch to the middle of a relatively big city. That was a culture shock. Having the same pop culture on both sides of that move felt stabilizing and Toby Keith played a part of that for me.

Further, the song is largely about the TV series Gunsmoke. For whatever reason, this show does not seem to be as well-remembered as it should be, given that it ran for 20 years and was incredible. But I became familiar with the show in the summer of 1991 while staying with my grandparents on their rural property. They lived about a 9 hour’s drive from the rural place where I lived, so this was a big trip, my parents couldn’t easily or quickly come get me early, and the experience proved to be formative. I remember seeing my parents and siblings driving away and wondering if I’d made a huge mistake, given that I was stuck with my pretty spur of the moment request not to leave. I hadn’t. My days were spent fishing, shelling beans, carrying lumber on occasion, and watching Gunsmoke and The Andy Griffith Show. It was a great time. My aunt, uncle, and cousins lived close by, too. A lot of the relationships I have with them, even now, was built on a foundation from that small window of time.

A few months after I got home, my grandpa was diagnosed with cancer. He passed away several months later. It ended up being lucky for me that I took the opportunity to stay with him when I could. I didn’t know it at the time, but it was the last opportunity I would ever have.

When the song was released (a year and a half after my parents dropped me off that summer in ’91) and while I was dealing with the shell shock of a major family relocation, the lyrics about Gunsmoke reminded me of watching TV with my late grandpa and it was comforting in a weird way to think that a lot of other people probably watched that show with their grandparents, too.

Should’ve Been a Cowboy has always been something familiar and familial for me. So is Toby, himself, for that matter. My entire family went to see Toby Keith together, live, at his 2013 Moore, Oklahoma tornado relief concert. It’s one of my favorite memories.

I was very bummed when Toby Keith passed away.

His restaurant is still open in Oklahoma City and if you’re ever in town, I highly recommend the Fried Bologna Sandwich as well as the Chips and Queso.