OldiesButGoodies

Country

Toby Keith – Should’ve Been A Cowboy

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Introduction:

“Should’ve Been a Cowboy” was the breakout single that launched Toby Keith’s career in country music. Written by Keith in 1993, the song emerged from an impromptu moment on a hunting trip in Dodge City, Kansas. Keith and his friends, dressed in hunting attire, were watching a fellow hunter attempt to ask a woman to dance, only to be rejected. This led one of Keith’s friends to quip, “You should’ve been a cowboy,” sparking an idea that would shape the song’s nostalgic and adventurous theme. Keith penned the song almost immediately, capturing the yearning for a romanticized Wild West life, complete with imagery of cowboy heroes like Roy Rogers and Gene Autry, and references to Western icons such as Gunsmoke​.

Upon its release as the lead single on Keith’s debut album, “Should’ve Been a Cowboy” became an instant success, reaching number one on the Billboard Hot Country Songs chart and remaining one of the most played country songs of the 1990s. Its appeal lay in the song’s vivid storytelling, coupled with Keith’s powerful vocals and relatable themes. The song has since been certified 4x Platinum by the RIAA and is celebrated as one of Keith’s defining hits, a staple of his live performances throughout his career​.

Reflecting on the song’s impact, Keith has expressed that it is “the foundation” of his career, marking it as his “career record” that remains close to his heart. Its enduring popularity has solidified Keith’s place in country music history, making “Should’ve Been a Cowboy” a timeless anthem of nostalgia and adventure.

Video:

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Merle Haggard’s childhood was becoming increasingly chaotic when something entered his life that would eventually change everything: a guitar. His older brother Lowell gave him one when Merle was around 12. Merle began teaching himself, absorbing the records and styles of country heroes such as Bob Wills, Lefty Frizzell and Hank Williams. There were no expensive lessons preparing him for Nashville. There was simply a troubled California kid listening closely and learning how another man’s sadness could live inside a melody. Merle would still make plenty of mistakes. Music didn’t instantly rescue him from running away, juvenile detention or eventually prison. But the guitar remained. Years later, millions would recognize Merle’s voice within seconds. Perhaps that’s because he wasn’t merely learning how to sing songs as a boy. He was slowly learning how to tell the truth about his own life.

Merle Haggard rarely needed to invent heartbreak. He had known it since childhood. In 1946, when Merle was only nine years old, his father, James Haggard, died following a stroke. For a boy who deeply needed his father’s presence, the loss became a turning point. His mother, Flossie, worked to support the family. Merle, meanwhile, became increasingly restless. He skipped school, ran away, got into trouble, and began a long journey through juvenile institutions that eventually led somewhere far darker. Looking back at his life, it is difficult not to see that nine-year-old boy behind many of the adult Merle Haggard’s songs. People later called him a rebel, an outlaw and a survivor. But before any of those labels existed, there was simply a grieving boy who had lost his dad—and never seemed to completely outrun that loss.

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