free hit counter Throwback to a night that now feels like lightning in a bottle—when Blake Shelton and Toby Keith lit up the 2018 ACM Awards with “Should’ve Been a Cowboy.” The crowd was on its feet, voices echoing across the room as artists in the audience sang along, caught in the magic of the moment. Looking back, it’s clear this wasn’t just a performance—it was a tribute in the making. No one, not even Blake, knew it would be the last time he’d share that stage, that song, that energy with Toby. Now, that memory hits like a freight train—loud, unforgettable, and full of heart. - FRESH

Throwback to a night that now feels like lightning in a bottle—when Blake Shelton and Toby Keith lit up the 2018 ACM Awards with “Should’ve Been a Cowboy.” The crowd was on its feet, voices echoing across the room as artists in the audience sang along, caught in the magic of the moment. Looking back, it’s clear this wasn’t just a performance—it was a tribute in the making. No one, not even Blake, knew it would be the last time he’d share that stage, that song, that energy with Toby. Now, that memory hits like a freight train—loud, unforgettable, and full of heart.

Throwback To When Blake Shelton & Toby Keith Sang “Should’ve Been A Cowboy” At The ACM Awards | Classic Country Music | Legendary Stories and Songs Videos
Blake Shelton joined Toby Keith to sing “Should’ve Been a Cowboy” at the 2018 ACM Awards. (Photo Credit: Jeff Kravitz / ACMA2018 / FilmMagic for ACM)

Blake Shelton & Toby Keith Throw Things Back With ACM Awards Duet

Blake Shelton and Toby Keith showcased their years-long friendship during an unforgettable duet at the ACM Awards in 2018.

The 2018 ceremony marked Shelton’s first performance at the ACM Awards in several years. After announcing his involvement, fans started wondering which song he’d perform.

The obvious choice seemed to be his then-current single “I Lived It.” Of course, it also made sense for him to perform “I’ll Name the Dogs,” which was nominated for an award.

However, although Shelton sang “I Lived It,” he also had another song on his plate. It would have been near impossible for anyone to guess what Shelton was going to sing, or who he’d sing it with.

Before the ceremony, the ACM revealed its plans to have special “ACM Throwback” performances. As stated in a press release issued at the time, these performances paired current stars with country icons to celebrate the 25th anniversary of songs released in 1993.

Fans were thrilled to see Shelton’s name in the lineup of artists participating in the throwback performances. It was even more thrilling to see that he’d be joining Toby Keith to sing his breakout hit, “Should’ve Been a Cowboy.”

Keith was celebrating the song himself that year. To mark 25 years since its release, he named his 2018 tour The Should’ve Been A Cowboy Tour XXV.

Now, This Performance Serves As A Way To Remember Toby

Shelton and Keith had the entire crowd on their feet during their performance at the 2018 ACM Awards. Many of the other artists could be seen singing along in the audience.

Based on the spectators’ responses, it seemed clear that Shelton and Keith’s collaboration was one of the best things that night! Even now, years later, you can’t deny how epic that moment was. Watch it in the video below.

Sadly, this performance now serves as a way to remember Toby Keith. He passed away at the age of 62 on February 5, 2024, following a years-long battle with stomach cancer.

After Keith died, his longtime buddy, Blake Shelton, paid tribute to him on social media. He wrote:

“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 by singing “I Love This Bar” when Keith was posthumously inducted into the Country Music Hall of Fame. He’s ensuring his friend’s legacy will live on forever…

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