Every #1 Single of the Nineties: Toby Keith, “Should’ve Been a Cowboy”

“Should’ve Been a Cowboy”

Toby Keith

Written by Toby Keith


#1 (2 weeks)

June 5 – June 12, 1993

Radio & Records

#1 (1 week)

May 28, 1993

A superstar launches his career with the most played song of the decade.

The Road to No. 1

Toby Keith was interested in music early, but he pursued football first, playing on junior high school and high school teams before graduating and beginning work in the oil fields of Oklahoma.  As work literally dried up, his side hobby of playing music at clubs evolved into a professional pursuit, but he kept up his football playing as well, featuring on a semi-professional team.

With his band Easy Money, he played around Oklahoma and Texas, and soon relocated to Nashville, where he struggled to find a record deal, but became popular in a local club.  A fan of his who was also a flight attendant passed his demo tape on to producer Harold Shedd, who liked what he heard.  After catching Keith live, he signed him to Mercury Records.

Keith was launched as part of a Triple Play promotion, a novel idea of presenting three new artists at the same time.  Shania Twain and John Brennen struggled out of the gate, but Keith shot straight to the top with his debut single.

The No. 1

“Should’ve Been a Cowboy” is the perfect suburban Country & Western song.

Keith’s imagination of what it would be like to a cowboy in the Wild West is shaped not by history, but by popular culture depictions of it, with the lyrics relying heavily on the characters and situations of the television show Gunsmoke.

It resonates as a fantasy constructed by Hollywood, romanticizing about the freedom of days gone by in a way that they never truly existed.  As country music and the country itself became more suburbanized, images of rural poverty or the violence of the Western expansion faded from the collective memory, this sort of romanticized nostalgia continued the tradition of the best country music.

But now, instead of longing for the simple times of living in the mountains or tiny rural towns, warm memories of the past could now include television shows and films from a simpler time.

Toby Keith was playing cowboy, but country music singers had been doing that for generations before him.  What made this song special was his openness about it, his willingness to join in on the fantasy of the listeners, rather than attempting to be that fantasy himself.

The Road From No. 1

Toby Keith’s debut album was a commercial hit, and it produced two more top ten hits – “He Ain’t Worth Missing” and “A Little Less Talk (and a Lot More Action)” – before the fourth single went No. 1.  We’ll cover it in 1994.

“Should’ve Been a Cowboy” gets an A.

Every No. 1 Single of the Nineties

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Next: Alabama, “Hometown Honeymoon”


  1. Yet another classic debut record from the early 90’s! Even though I’ve likely heard it a million times by now, I’m somehow still not tired of hearing it, and I honestly don’t think I ever will be. The excitement in Toby’s performance coupled with the catchy melody is such a perfect fit as the narrator in the song imagines what his life would’ve been like as a cowboy back in the old west, and it’s still just as captivating today. I’ve always loved that guitar solo, as well! Even the video is still fun for me to watch, and it’s another I’d always enjoy on GAC Classic. Btw, Toby is another who had quite a nice mullet in the early 90’s.

    Just like the Dwight Yoakam song previously, I also have no recollection of actually hearing this one during 1993 (Again, I was mainly listening to oldies radio by this time). However, unlike the Dwight song, I heard this one countless times as a recurrent when I got back into listening to country radio regularly in the mid 90’s, and I always liked it. I remember one time (1996-1997ish, I guess) hearing it on a countdown show, and being surprised to hear that it was from 1993, since it was still a fairly “new” song to me, and I had already thought of most early 90’s and 80’s country songs as “old.”

    Toby Keith was also an artist I didn’t get familiar with until my return to country in the mid 90’s (I do recall occasionally hearing “Wish I Didn’t Know Now” and “A Little Less Talk” in the car with my dad when they were new, but I didn’t know who sang them at the time). I always liked everything I heard from him, though, and he quickly became one of the more recognizable “newer” voices on the radio for me during that time. I didn’t get an album of his until around 2001 when I picked up a copy of his self-titled debut, since I was into collecting debut albums from 90’s country artists back then. That’s actually still one of my favorite albums of his, and I love the production by Nelson Larkin and Harold Shedd. It’s actually quite similar in places to the work they did with Earl Thomas Conley and Billy Joe Royal in the 80’s. I even hear a bit of an ETC influence in Toby’s vocals in a lot of his earlier stuff, especially.

    Looking back, it’s just crazy to think that future superstars like Toby, Shania, Tim McGraw, and Faith Hill were all making their debuts in 1993, not long after I temporarily stopped listing to country radio regularly, and how quickly the landscape was changing then. Heck, even Martina was about to finally make her big breakthrough later that year. Btw, it’s too bad that John Brannen wasn’t quite as successful. I actually have his 1993 debut on Mercury, and I absolutely love it! He had a great unique voice and country-rock style. “Moonlight & Magnolias” should’ve been a hit, especially, imho.

  2. The best indicator of strong this song is, is how vital and fresh it still sounds today. An absolutely essential contemporary thread of the western theme that is woven throughout the history of country and western music. Another classic!

    All its entertainment references to tv shows and movies made the cowboy relatable to me in ways older western music from Marty Robbins couldn’t, even as I adored his work.

    Jamie- I am also a fan of John Brannen! I love “Neon Ballet” from his “Scarecrow” album from 2000.

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