Carrie Underwood Honors The Late Toby Keith With Heartfelt Reflection And Touching Tribute Performance

“I thought we would honor him tonight by singing one of his songs,” Underwood shared before going into a cover of Keith’s “Should’ve Been A Cowboy.”

By

Andrew Wendowski

Andrew Wendowski is the Founder and CEO of Music Mayhem. As a 29-year-old entrepreneur, he oversees content as the Editor-In-Chief for the independent brand. Wendowski, who splits time between Philadelphia, Penn., and Nashville, Tenn., has an extensive background in multimedia. Before launching Music Mayhem in 2014, he worked as a highly sought-after photojournalist and tour photographer, collaborating with such labels as Interscope Records and Republic Records. He has captured photos of some of the biggest names, including Taylor Swift, Metallica, Harry Styles, P!NK, Morgan Wallen, Carrie Underwood, The Rolling Stones, Madonna, Shania Twain, and hundreds more. Wendowski’s photos and freelance work have appeared nationwide and can be seen everywhere from ad campaigns to various publications, including Billboard and Rolling Stone. When Wendowski isn’t running Music Mayhem, he enjoys spending time at concerts, traveling, and capturing photos.

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Posted on April 15, 2024

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Carrie Underwood, Photo Courtesy of Chris Hollo/Opry

Carrie Underwood honored late country music icon, Toby Keith, with a touching reflection of a moment she shared with him that she will cherish forever and a performance of one of Keith’s signature tunes, “Should’ve Been A Cowboy.” Underwood’s tribute took place during her set at the Grand Ole Opry on Saturday evening (April 13), a night that also featured performances from Nate Smith, Connie Smith, Vince Gill and more.

Carrie Underwood Reflected On Cherished Moment Shared With Toby Keith

The country superstar began by reflecting on a treasured moment she shared with the “Red Solo Cup” singer a few years ago.

“So one of the most special things about getting to play at the Opry is not just the music, but it’s the people you get to hang out with while you’re here, and as an artist you can have some really cool moments that can’t be duplicated anywhere else,” Underwood explained, before detailing a special moment she shared with Toby Keith backstage at the Opry several years ago.

Underwood then shared, “A few years back, I had one of those nights that I will always remember and always treasure. I was playing the night that Toby Keith was playing. I had always been around him, I’ve always said hi, and had short little conversations at like awards shows and stuff like that. But, he asked me to come on his bus and I got to go and hang out with him for a little bit. It was a night that I will always cherish. We talked Oklahoma, and feel like we got along pretty well. He was just a good one, so I thought we would honor him tonight by singing one of his songs.”

Covered “Should’ve Been A Cowboy”

Donning an elegant periwinkle dress complete with silver sparkles, Underwood went on to deliver a touching tribute performance. She covered one of Toby Keith’s most iconic hits, “Should’ve Been A Cowboy.”

“I should’ve been a cowboy / I should’ve learned to rope and ride / Wearin’ my six-shooter, ridin’ my pony on a cattle drive / Stealin’ the young girls’ hearts / Just like Gene and Roy / Singin’ those campfire songs / Woah, I should’ve been a cowboy,” Underwood sang on the tune’s chorus alongside her band.

Previously Honored Toby Keith at 2022 BMI Awards

This isn’t the first time Carrie Underwood has honored Toby Keith. In November of 2022, Underwood was on hand to pay tribute to her fellow Okie during the 70th annual BMI Awards, where Toby Keith was being honored with the BMI Icon Award.

At the event, which took place at Broadcast Music Inc (BMI) on Music Row in Nashville, Underwood delivered a special performance of Keith’s first chart-topping hit, “Should’ve Been A Cowboy.”

“It was artists like you that taught kids like me that greatness is possible,” Underwood said at the time before going into her performance as Toby Keith watched on from the star-studded audience. Joined by a two-piece band, the powerhouse vocalist then belted out the lyrics to Keith’s 1993 breakout hit.

Carrie Underwood & Toby Keith; Photo by Erika Goldring/Getty Images for BMI
Carrie Underwood & Toby Keith; Photo by Erika Goldring/Getty Images for BMI

Toby Keith Passed Away In February of 2024

Toby Keith died on February 5, 2024 following a battle with stomach cancer. A representative for the country music icon shared the sad news with fans via a statement on his official website and social media profiles.

“Toby Keith passed peacefully last night on February 5th, surrounded by his family” the statement read. “He fought his fight with grace and courage. Please respect the privacy of his family at this time.”

Toby Keith; Photo by Greg Watermann
Toby Keith; Photo by Greg Watermann

He was diagnosed with stomach cancer in October of 2022, but didn’t reveal his diagnosis with fans until June of 2022. At that time, he was also forced to cancel all of his scheduled concerts to focus on his health.

With 32 No.1 singles and 44 million albums sold, Toby Keith was regarded as one of country music’s biggest hitmakers. He wrote a chart-topping hit every year for 20 consecutive years, including “How Do You Like Me Now?!,” “Courtesy of the Red, White, & Blue (The Angry American),” “I Love This Bar,” “Beer For My Horses,” and “As Good As I Once Was.”

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Written by

Andrew Wendowski is the Founder and CEO of Music Mayhem. As a 29-year-old entrepreneur, he oversees content as the Editor-In-Chief for the independent brand. Wendowski, who splits time between Philadelphia, Penn., and Nashville, Tenn., has an extensive background in multimedia. Before launching Music Mayhem in 2014, he worked as a highly sought-after photojournalist and tour photographer, collaborating with such labels as Interscope Records and Republic Records. He has captured photos of some of the biggest names, including Taylor Swift, Metallica, Harry Styles, P!NK, Morgan Wallen, Carrie Underwood, The Rolling Stones, Madonna, Shania Twain, and hundreds more. Wendowski’s photos and freelance work have appeared nationwide and can be seen everywhere from ad campaigns to various publications, including Billboard and Rolling Stone. When Wendowski isn’t running Music Mayhem, he enjoys spending time at concerts, traveling, and capturing photos.

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