Blake Shelton & Toby Keith’s Iconic “Should’ve Been A Cowboy” Duet at the ACM Awards: A Moment That Lives On

In one of the most unforgettable performances in ACM Awards history, Blake Shelton and Toby Keith took the stage together in 2018 to perform a spirited rendition of Keith’s legendary hit, “Should’ve Been a Cowboy.” The moment was more than a musical throwback—it was a heartfelt celebration of friendship, legacy, and the enduring spirit of country music.

The performance came as part of the ACM’s special “Throwback” segment, launched to honor the 25th anniversary of chart-topping country songs from 1993. Fans were elated to see Shelton’s name among the featured artists, but few expected the powerful surprise of him sharing the stage with Toby Keith—a country legend who had inspired generations of artists.

Shelton had already performed his own single, “I Lived It,” earlier that night, but it was this collaboration with Keith that truly stole the show. As soon as the opening chords of “Should’ve Been a Cowboy” rang out, the crowd erupted. Artists in the audience were seen singing along, dancing, and giving the duo a rousing standing ovation. It was a celebration of country music’s past, present, and future, led by two of the genre’s most beloved figures.

Toby Keith, who had just launched his Should’ve Been a Cowboy Tour XXV in honor of the song’s 25th anniversary, was in top form. With Shelton by his side, the performance became a highlight of the night and a favorite among fans long after the curtain closed.

A Tribute That Means Even More Today

In hindsight, the 2018 duet has taken on even deeper meaning. Toby Keith passed away on February 5, 2024, at the age of 62 after a courageous battle with stomach cancer. The performance, once a joyful throwback, now stands as a touching reminder of the impact Keith had on country music and on those who called him a friend.

Following Keith’s passing, Blake Shelton paid an emotional tribute, writing on social media:

“Even though I knew about your battle these last few months, I still never imagined this day. Anyone who knew you knows what I mean. You were the toughest man I ever met. Thank you, brother, for being a friend, a hero, and an inspiration. There will never be another Toby Keith.”

In October 2024, Shelton honored Keith once more by performing “I Love This Bar” at the Country Music Hall of Fame induction ceremony, where Keith was posthumously honored for his legacy.

A Legacy That Lives On

Though Toby Keith is no longer with us, moments like this 2018 ACM Awards duet with Blake Shelton ensure his legacy lives on. It wasn’t just a performance—it was a celebration of friendship, country roots, and the songs that define generations. And for fans everywhere, it remains a moment worth remembering.