Introduction

This may contain: a man wearing a cowboy hat pointing at the camera with an image of himself in the background

“Should’ve Been a Cowboy” stands as a landmark in country music, marking the debut of Toby Keith’s illustrious career. Released on February 12, 1993, as the lead single from his self-titled debut album, the song quickly ascended to the top of the Billboard Hot Country Songs chart by June of that year. Its success was not fleeting; the track became the most-played country song of the 1990s, solidifying Keith’s place in the genre’s history.

The inspiration for “Should’ve Been a Cowboy” struck Keith during a hunting trip in Dodge City, Kansas. Observing a friend’s unsuccessful attempt to ask a woman to dance, only to see her later accept a cowboy’s invitation, a companion quipped, “I guess you should’ve been a cowboy.” This remark resonated with Keith, prompting him to pen the song in a hotel bathroom that same night.

Lyrically, the song romanticizes the cowboy lifestyle, referencing iconic Western figures and media. Mentions of “Marshal Dillon” and “Miss Kitty” nod to the television show “Gunsmoke,” while allusions to Jesse James, the Texas Rangers, and singing cowboys like Gene Autry and Roy Rogers evoke a sense of nostalgia for the Old West. The chorus encapsulates this sentiment, with Keith lamenting missed opportunities to embody the adventurous spirit of a cowboy.

Musically, the track features a blend of honky-tonk guitar riffs and pedal steel melodies, complementing Keith’s twangy vocals. This combination creates an upbeat and catchy tune that resonated with audiences, contributing to its enduring popularity.

The song’s impact extended beyond the charts. It became a staple at sporting events, particularly at Oklahoma State University, where it was frequently played to celebrate victories. Over the years, numerous artists have covered the song, and it has been featured in various media, further cementing its status in country music lore.

Reflecting on its significance, Keith has acknowledged that “Should’ve Been a Cowboy” laid the foundation for his career. Its success not only introduced him to the country music scene but also established a legacy that continues to influence artists and listeners alike.

Video

You Missed

At 89, Engelbert Humperdinck is no longer just the velvet voice that once defined romance for millions — he is a man standing alone in the quiet after the applause, carrying a love story that even time could not silence. Gone are the roaring stages and dazzling lights. In their place: a trembling confession, eyes glistening, voice unsteady as he speaks of the woman who was never just his wife — but his anchor, his inspiration, his forever. After more than half a century side by side, illness took her from this world… but never from his heart. “She’s still with me,” he whispered — and in that fragile moment, the world seemed to pause. For decades, fans believed his greatest love songs were performances. Now we know they were promises. Promises whispered in hospital rooms. Promises carried through sleepless nights. Promises that did not break when her hand slipped from his. This is not the story of a superstar. This is the story of a husband who still sets a place for her in his memories. Of a man who sings not to an audience — but to the love of his life, wherever she may be. Because for Engelbert, love was never about spotlight or roses. It was loyalty through suffering. Devotion through fading strength. A bond that outlived breath itself. And perhaps that is why his words cut so deeply now. True love doesn’t die when a heartbeat stops. It lingers — in photographs, in melodies, in quiet conversations with the past. It lives on in every note he sings… and in every tear shed by those who finally understand that the greatest romance of his life was never written in lyrics — but in a lifetime of unwavering love.