Throughout his incredible career, Toby Keith has wowed audiences at countless awards shows with his unforgettable performances and charming personality. In this roundup, we’ll take a look at 10 of Toby Keith’s most memorable awards show moments that had fans cheering, singing along, and most importantly, they’re the ones that will forever be etched in our memories as part of Toby’s remarkable legacy.

1. “Courtesy of the Red, White and Blue” at the 37th CMA Awards

Toby Keith’s performance of “Courtesy of the Red, White and Blue” at the Country Music Awards stands as a memorable moment in country music history. Just months following the tragic events of September 11th, 2001, Keith took to the stage at the 37th Annual CMA Awards in 2002 to deliver his patriotic anthem. Released in May 2002 as the lead single from his multi-platinum album “Unleashed,” the song swiftly climbed the charts, reaching number 25 on the Billboard Hot 100– marking Keith’s biggest solo hit. With lyrics that pay homage to his father’s military service, the performance resonated deeply with audiences, both in attendance and those watching from afar, serving as a powerful tribute during a time of national tragedy.

2. Toby Keith And Kristen Bell Co-Host The CMT Awards

The 2012 CMT Music Awards will always be remembered for the dynamic duo that took center stage as hosts: country music superstar Toby Keith and actress Kristen Bell. Their collaboration brought a fresh and entertaining energy to the event, infusing the night with humor and charm. As they shared the stage, Keith and Bell captivated audiences, creating unforgettable moments that added an extra layer of excitement to an already star-studded evening.

3. Toby Keith Wins First “Entertainer of the Year” Award At The ACM’s (And Left Before Finding Out)

In 2003, Toby Keith achieved a significant milestone in his career by winning his first Entertainer of the Year Award at the ACM Awards. The evening became unforgettable, not just because of Keith’s victory in the category, but also due to the unexpected circumstances surrounding his absence when the winner was announced. Reports surfaced that Keith had left the venue before the award was presented, due to him feeling snubbed after not receiving recognition in other categories. Despite his absence during the announcement, Keith’s win marked an achievement in his career and remains a memorable highlight in the history of the ACM Awards.

4. Toby Keith’s Red Solo Cup Performance At The 2012 ACM Awards

At the 2012 ACM Awards, Toby Keith delivered a lighthearted and entertaining performance of his hit song “Red Solo Cup” that left the entire audience laughing, smiling, and enthusiastically joining in. The stage was set with a lively atmosphere as the crowd waved red solo cups in unison, adding to the fun. With some surprise celebrity appearances sprinkled throughout, Keith’s rendition of the catchy tune was a playful and amusing highlight of the night, leaving a lasting impression on all who witnessed it.

5. Toby Keith And Willie Nelson Sing “Beer For My Horses At The CMA’s

The 2003 CMA Awards witnessed an unforgettable collaboration between two country music legends, Toby Keith and Willie Nelson, as they delivered a stellar performance of “Beer for My Horses.” Taking the stage together, Keith kicked off the performance with his guitar and vocals, setting the stage for a memorable rendition. As the song progressed, Nelson joined in, seamlessly alternating verses and harmonizing together flawlessly during the chorus. The chemistry between the two icons was undeniable, and their combined talent created a timeless moment in country music history.

6. Toby Keith Wins The BMI Icon Award

At the BMI Awards, where songwriters, publishers, and country music stars gather to celebrate their talents, Toby Keith snagged a big win in 2022. He received the prestigious BMI Icon Award, joining the ranks of legends like Dolly Parton, Willie Nelson, and more. This award recognizes Keith’s huge impact on country music, cementing his status as one of the greats in the industry.

7. Toby And His Daughter Sing “Mockingbird” At the CMA’s

Who could forget the heartwarming moment when Toby Keith and his daughter, Krystal Keith, took the stage together at the 2004 CMA Awards? It’s been twenty years since this unforgettable performance, where the father-daughter duo captivated the audience with their rendition of “Mockingbird,” proving that talent runs in the Keith family.

8. Toby Keith And Blake Shelton Sing “Should’ve Been a Cowboy”

At the 2018 ACM Awards, country music icons Toby Keith and Blake Shelton teamed up for a show-stopping duet performance of Toby’s chart-topping hit “Should’ve Been a Cowboy.” The duo delivered an electrifying rendition that had the crowd on their feet, making it an award show moment that is unforgettable.

9. Toby Keith Pays Tribute to Merle Haggard At ACC Awards

At the 2016 American Country Countdown Awards, Toby Keith paid a heartfelt tribute to the late country music legend, Merle Haggard. With respect and admiration, Keith’s tribute struck a chord with the audience, reminding everyone of Haggard’s lasting impact on country music. Through his tribute, Keith celebrated the life and music of one of country’s greatest, ensuring that Haggard’s legacy lives on in the hearts of fans everywhere.

10. Toby’s Last Award Show Performance

At the inaugural People’s Choice Country Awards in September of 2023, Toby Keith made a special appearance despite his ongoing battle with stomach cancer. It was his first time back on stage since revealing his diagnosis. With a heartfelt rendition of “Don’t Let the Old Man In,” Keith moved the audience to tears, showing his strength and love for music. He was also honored with the Icon Award for his incredible career. Sadly, this turned out to be Toby’s final performance at an award show before he passed away.