Few songs in country music history have stood the test of time like Toby Keith’s debut single, Should’ve Been a Cowboy. Originally released in 1993, the song marked the beginning of a legendary career and remains one of the most iconic tracks in modern country music. With the release of Should’ve Been a Cowboy Live XXV in 2018, Toby Keith honored the 25th anniversary of his breakthrough hit with a powerful and heartfelt performance that reminded fans why this song remains a timeless anthem.
A Cowboy's Journey Begins
When Should’ve Been a Cowboy first hit the airwaves in the early ‘90s, it quickly climbed to the top of the Billboard Hot Country Songs chart. The song told the nostalgic tale of a man yearning for the freedom and adventure of the Old West. With lyrics that referenced cowboy icons like Gene Autry and Roy Rogers, Keith struck a chord with listeners who dreamed of open skies and simpler times.
The single catapulted Toby Keith into stardom. It became the most-played country song of the 1990s, with over three million radio spins—cementing its place in country music lore.
Live XXV: A Stirring Tribute to a Classic
Fast-forward to 2018, and Keith released Should’ve Been a Cowboy Live XXV, a commemorative performance that celebrated the silver anniversary of the track that launched it all. Recorded live, the XXV version captures Toby Keith’s enduring charisma, storytelling prowess, and vocal strength that remained as compelling as ever.
In this version, Keith doesn't just perform the song—he relives it. From the opening guitar riff to the final chorus, the energy of the live audience fuels a performance full of grit, soul, and nostalgic power. His delivery is both reverent and invigorating, as though he’s tipping his hat to the cowboy spirit that first defined him.
A Song That Transcends Generations
What makes Should’ve Been a Cowboy more than just a chart-topping hit is its cultural footprint. The song became an anthem at college tailgates, country music festivals, and karaoke bars across the nation. It spoke to a universal longing for freedom, romance, and a life lived on one’s own terms.
Even younger generations, many of whom weren’t even born when the song was first released, have embraced it. Keith’s ability to bridge the past and present with his Live XXV rendition showed just how timeless this cowboy dream remains.
Honoring a Legend: Tribute Performances After Keith’s Passing
Following Toby Keith’s passing in early 2024 due to stomach cancer, Should’ve Been a Cowboy took on an even deeper meaning. The country music community rallied around his memory with emotional tributes that highlighted the song’s legacy and the man behind it.
At the 59th ACM Awards, Jason Aldean gave a stripped-down, acoustic performance of Should’ve Been a Cowboy that left the audience in tears. The camera panned to Keith’s family, who were visibly moved by the heartfelt tribute. Aldean’s rendition was not just a performance—it was a farewell to a friend and a pioneer.
Later, at the Stagecoach Festival, Jelly Roll and T-Pain surprised fans with their own take on the song. The unexpected duo delivered a soulful, genre-blending cover that honored Keith’s fearless spirit. All proceeds from the performance were donated to the Toby Keith Foundation, continuing his legacy of supporting families facing pediatric cancer.