The late great Toby Keith is one of the most beloved and successful country musicians of all time. The start of that success and lovability started today, on June 5, 1993, as Keith garnered his first ever No. 1 hit with the single, “Should’ve Been A Cowboy”. For Keith, this song seemed to mean much more than just a No. 1; it was also his introduction to the masses and the very song that started his journey to becoming a chart-topping country artist.
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Released as the first track on his self-titled debut album, Toby Keith, “Should’ve Been A Cowboy” was released on April 20, 1993. Months later, Keith’s iconic track peaked at No. 1 on the Billboard Hot Country Songs. Furthermore, it also impressively and somewhat surprisingly given the times, peaked at No. 93 on the Billboard Hot 100.
In addition to its successful chart run, Keith’s single also earned a quadruple Platinum certification from the RIAA. Above all, this is the moment that started Keith’s decorated and dominating 31-year country music career. After this, Toby Keith soared to the top, and everything for him went up.
Remembering Toby Keith’s Illustrious Chart-Topping Career
After Keith released “Should’ve Been A Cowboy”, he became arguably the biggest country singer of the 1990s. This unofficial title is thanks to his 20 No. 1 hits, 42 top 10 hits, and three CMA Awards. Of those 20 No. 1 hits, some of Keith’s most notable include “How Do You Like Me Now?”, “I Love This Bar”, “Red Solo Cup”, and “As Good As I Once Was”.
As most country music fans know, Keith’s career was not all about No. 1 hits, shiny awards, and RIAA certifications. It was also about entertainment, camaraderie, celebration, patriotism, and, in essence, about enjoying the simple things this life has to offer.
When Toby Keith passed away in 2024, he left all of those sentiments behind in his legacy. However, without “Should’ve Been A Cowboy”, Keith might have never gotten the chance to deliver those sentiments to the masses. Luckily, we don’t live in that reality. Rather, we live in a reality where Toby Keith’s impact on country music will never be forgotten nor dismissed. Frankly, thanks to his success, his legacy is seemingly inescapable, as it touches every corner of the industry. That legacy started today, June 5, 1993, when the acclaimed single, “Should’ve Been A Cowboy”, delivered Keith his first No. 1 hit.
Photo by M. Caulfield/WireImage
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