Luke Bryan Honors Toby Keith With ‘Should’ve Been A Cowboy’ Wearing A Special Hat Gifted To Him By His Late Sister
“I’m just an old country boy from Georgia but Toby Keith certainly made me wanna be a cowboy,” Bryan declared.

Luke Bryan; Photos by Tibrina Hobson/Getty Images for Universal Music Group
Luke Bryan‘s performance of “Should’ve Been A Cowboy” on the NBC special, Toby Keith: American Icon, was an emotional tribute that resonated deeply with Keith’s family and viewers alike. Not only did Bryan honor the late country music legend, but he also wore a cowboy hat gifted to him by his late sister before her passing, adding a personal and heartfelt touch to the already emotional performance.
Stepping onto the stage inside Nashville’s Bridgestone Arena, Bryan said it was an “honor” to have the opportunity to celebrate Toby Keith, who he referred to as “the best ever.”

“Toby Keith was just a bada** dude. I got to hang with him a couple of times. He just always left the room telling the best jokes. He always had a song that he had written that very few people got to hear that he would play for you he was just doing so many things under the radar that were so special to a young up-and-coming artist like me,” he shared.
The emotions began to run high as he stepped away from the microphone to grab a special cowboy hat from the stage behind him.
“This hat has been hanging in my closet for probably 15 years,” Bryan explained. “My sister, down in Georiga when I was playing bars and doing about 10 Toby Keith songs a night, my sister bought me this hat. I used to wear this hat every night. Ever since I lost my sister, I hadn’t put this hat on stage in a lot of years. I was walking out the house and I said you know what, ‘I’m just an old country boy from Georgia but Toby Keith certainly made me wanna be a cowboy and I’m gonna be a cowboy tonight.”
The audience erupted with cheers as Bryan declared, “This is for you, Toby!”
He went on to deliver a standout performance of Toby Keith’s iconic debut hit, “Should’ve Been A Cowboy.”
Before the show, we caught up with Bryan who told us that was his first song choice when he got the opportunity to participate in the show.
“It’s going to be good,” Bryan teased. “Well, what’s funny is they called me and then some artists had taken some songs and I was like, ‘Is ‘Should’ve Been a Cowboy’ still available?’ And they were like, ‘Yeah.’ I was like, ‘There’s no practice needed for that one! I know that one.’”
He later added, “Tonight’s about honoring his legacy…he’s just gone too soon from us and he had a lot more to give.”
Luke Bryan was just one of the country superstars who dropped everything to honor the late Toby Keith. The two-hour special also included performances and special appearances from Trace Adkins, Priscilla Block, Eric Church, Jordan Davis, Scotty Emerick, Brett Favre, Brantley Gilbert, Riley Green, HARDY, Tyler Hubbard, Jamey Johnson, Krystal Keith, Ella Langley, Mac McAnally, Ashley McBryde, Parker McCollum, Leanne Morgan, Darius Rucker, Carrie Underwood, Clay Walker, and Lainey Wilson.

In addition to an array of musical performances spotlighting Keith’s incredible music and songwriter, Keith’s compassion and philanthropy were also highlighted throughout the special as the event supported Monroe Carell Jr. Children’s Hospital at Vanderbilt and The Toby Keith Foundation’s OK Kids Korral. Families from both organizations appeared to share their stories of receiving vital care and support during their most challenging times.
Toby Keith: American Icon aired on Wednesday, August 28 at 9 pm ET/PT on NBC. The show will be available to stream the following day on Peacock.
Country music legend Toby Keith passed away on February 5, 2024, following a battle with stomach cancer. Throughout his career, he earned an impressive 32 No.1 singles and sold a whopping 40 million albums.

It’s no surprise that he is regarded as one of country music’s biggest hitmakers after earning 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.”
He is a recipient of the National Medal of Arts, he’s been inducted into the Nashville Songwriters Hall of Fame (following his induction into the all-genre Songwriters Hall of Fame in 2015), and has been honored with the Academy of Country Music’s esteemed Merle Haggard Spirit Award.
Throughout his career, the Oklahoma native received the BMI Icon Award as well as the BMI Country Songwriter of the Year award three times, and his hit single “As Good As I Once Was” was awarded BMI’s Country Song of the Year in 2006.
Toby Keith’s music has garnered more than 10 billion streams and 100 million terrestrial radio spins to date.
Lauren Jo Black is a longtime country music journalist, editor, host, and media personality whose work has helped shape the conversation around country music for nearly two decades. As the current Editor-in-Chief of Country Now, she has become one of the genre’s most respected voices, interviewing hundreds of country music’s biggest stars, including Dolly Parton, Garth Brooks, Reba McEntire, Shania Twain, Randy Travis, Luke Bryan, Carrie Underwood, Blake Shelton, Luke Combs, and countless others. Over the course of her career, Black’s written work and interviews have reached billions of country music fans worldwide. A 2009 graduate of the University of Central Florida, Black began her career by founding Country Music Is Love, one of country music’s earliest independent digital publications, which she later sold to a major record label in 2015 before it was rebranded as Sounds Like Nashville. She then served as the publication’s Editor-in-Chief for more than two years. Her work has also appeared in Forbes, and she previously served as the Country Music Expert for Answers.com. Widely recognized for her expertise, Black has appeared as a featured guest on The Bobby Bones Show, BobbyCast, and Scripps News Morning Rush, providing insight on country music’s biggest moments. She has also hosted Country Now Live, a concert series featuring performances from artists including Lady A, Dierks Bentley, Riley Green, Jordan Davis, Dustin Lynch, Gabby Barrett, Brett Young, Jon Pardi, Kip Moore, Chris Young, and more. The series has welcomed thousands of fans in person while reaching millions more online. In addition, she hosted Connect With Country Now, a weekly interview series featuring conversations with rising country stars. Throughout her career, Black has earned a reputation for discovering and championing artists long before they become household names. She has covered Luke Bryan since the early days of his career, beginning when he was writing songs for other artists, including Billy Currington’s No. 1 hit “Good Directions,” before stepping into the spotlight with his debut single, “All My Friends Say” and eventually becoming one of biggest names in music. She also gave Megan Moroney her first opportunity to walk a major red carpet as Country Now’s official guest correspondent at the 2022 CMA Awards. An interview she conducted in 2018 for Forbes.com with Luke Combs that inspired his multi-week No. 1 hit, “Doin’ This.” She has also hosted stages at CMA Fest, moderated an industry panel at Country Radio Seminar, and helped lead important conversations about the evolving landscape of country music media. Beyond journalism, Black has also used her platform to support charitable causes and highlight organizations making an impact. Through Country Now Live, she has helped raise awareness and support for St. Jude Children’s Research Hospital, while also advocating for animal rescue through Country Now’s Pupdate series, spotlighting organizations including MuttNation Foundation, Wags & Walks, and Proverbs 12:10 Animal Rescue. Black has been recognized as one of Country Aircheck’s Women of Influence and received the 2012 Rising Star Award from the University of Central Florida. She is a longtime member of both the Country Music Association (CMA) and the Academy of Country Music (ACM). After nearly 20 years covering country music, Lauren Jo Black has spent her career telling the stories behind the artists, songs, and moments that have shaped the genre. Her first-ever book, Country Music Forever: An A-to-Z Celebration of Icons, Songs and Stories, brings that same passion and firsthand knowledge to the page, celebrating not only the legendary artists and timeless songs that have become the soundtrack to generations of fans, but also the places, traditions, and cultural moments that have made country music one of the most beloved genres around the world.







