Jelly Roll Pays Tribute to Toby Keith on New Year’s Eve With Another Emotional ‘Should’ve Been a Cowboy’ Cover

Jelly Roll Honors Toby Keith on NYE With ‘Should’ve Been a Cowboy’ Cover × Skip to main content Open menu Search Click to Expand Search Input Billboard Billboard Search Click to Expand Search Input LOGIN Login Account Manage Account Log Out Account Search Click to Expand Search Input Charts Music Video Shop Awards Business Billboard Charts Music Video Shop Awards Business LOGIN Login Click to Expand Search Input Account Manage Account Log Out Account Billboard Hot 100 Year-End Charts AI & Music Get Up Anthems by Tres Billboard Music Awards Family Global News Español Open menu Search Click to Expand Search Input Billboard Billboard Search Click to Expand Search Input LOGIN Login Account Manage Account Log Out Account Search Click to Expand Search Input Charts Music Video Shop Awards Business Country 01/2/2025 Jelly Roll Pays Tribute to Toby Keith on New Year’s Eve With Another Emotional ‘Should’ve Been a Cowboy’ Cover Jelly has performed the late country icon’s debut 1993 single several times since Keith’s death at 62 in February. By Gil Kaufman Gil Kaufman More Stories by Gil Kaufman Jelly Roll Pays Tribute to Toby Keith on New Year’s Eve With Another Emotional ‘Should’ve Been a Cowboy’ Cover Ava Max Asks Fans to ‘Respect My Art’ and Not Leak Her Songs Britney Spears Ex-Husband Sam Asghari Goes Instagram Official With New Girlfriend View All 01/2/2025 Share on Facebook Share on X Share to Flipboard Share on Pinterest + additional share options added Share on Reddit Share on LinkedIn Share on Whats App Send an Email Print this article Post a Comment Share on Tumblr Jelly Roll performs on stage during New Year’s Eve Live Nashville’s Big Bash at Bicentennial Capitol Mall State Park on December 31, 2024 in Nashville, Tennessee. Jason Davis/Getty Images Jelly Roll celebrated the end of the year with another homage of one of his musical heroes. During the Nashville’s Big Bash New Year’s Eve special on Tuesday night (Dec. 31), the singer performed Toby Keith’s 1993 debut single, “Should’ve Been a Cowboy” as part of a five-song set that also included his own hits “I Am Not Okay,” “Need a Favor,” “Son of a Sinner” and “Liar.” Related Jelly Roll & Bunnie XO Laugh About Her ‘Terrible’ Baking Skills in Sweet Video 12/26/2024 “I would like to dedicate this newt song to one of the greatest country music superstars that ever lived,” Jelly told fans . “In his memory, God rest your soul Big Dog Daddy, Toby Keith baby!” Jelly has performed “Cowboy” live a number of times since Keith died in February 2024 at age 62 from stomach cancer. He rolled out the cover for the first time at the Stagecoach Festival in April, when he was joined by T-Pain for a run through the song; the pair also dropped a recorded version of the track for Amazon Music. Trending on Billboard “I had been covering ‘Should’ve Been a Cowboy’ for about a year now at most of my shows, just kind of honoring Toby as he was getting sick before he passed away,” Jelly Roll, 40, told Variety at the time, noting that he got the blessing to release his version from Keith son, Stelen, who saw a video of Jelly’s version and called it one of the best he’d ever seen. “Then I really started chewing on, man, what better place to honor Toby than Stagecoach? Plus, Toby Keith was one of the artists that from afar, even though he would never have known it, encouraged me to do country music.” Funds raised from the cover were earmarked for the Toby Keith Foundations, which aids pediatric cancer patients. Jelly Roll was also part of an all-star celebration of Keith’s life at Bridgestone Arena on July 29 taped for the NBC TV special Toby Keith: American Icon , which also featured Luke Bryan, Eric Church, Ashley McBryde, Darius Rucker, Carrie Underwood and many more. Get weekly rundowns straight to your inbox Sign Up Read More About Country Music News Want to know what everyone in the music business is talking about? Get in the know on Visit Billboard Pro for music business news Trending Selena Gomez & Fiancé Benny Blanco Ring in the New Year With Sweet New Photos Leo Dan, Argentine Singer-Songwriter, Dies at 82 From Stray Kids to BTS Members & More, Which Is Your Favorite K-Pop Album of 2024? Vote! Not All Beatles Would Receive Grammys If ‘Now and Then’ Wins Primus Return to the Stage for First Show Since Departure of Drummer Tim Alexander The Daily A daily briefing on what matters in the music industry Email Address Sign Up Sign Up By providing your information, you agree to our Terms of Use and our Privacy Policy . We use vendors that may also process your information to help provide our services. // This site is protected by reCAPTCHA Enterprise and the Google Privacy Policy and Terms of Service apply. Icon Link PMC Logo Most Popular Where to Stream ‘Wicked’ Online Dwight Howard Responds To Fans Warning Fiancée Amy Luciani About His Past: “Move Along” Unauthorized Sports Streaming Sites Closed After Crackdown Why Blue Ivy’s Christmas Day Performance With Mom Beyoncé Was a Major ‘Steppingstone’ in Her Career You May Also Like Loading… ‘Astro Bot’ Wins Game of the Year at 2024’s The Game Awards: See Full Winners List 3 weeks ago Cordae Finally Explains YBN Disband: “There Are Some Things That Can’t Be Undone” 4 hrs ago The 18 Best Designer Work Bags for Women to Commute in Style 3 months ago Jordan’s Jock Juice Lands Jeter and Serena, but Is Tequila Craze Cooked? 8 months ago Billie Eilish’s ‘Birds of a Feather’ Is Spotify’s Most-Streamed Song of 2024 4 hrs ago Customer Service Billboard About Us Accessibility Advertise Shop Events Careers Contact Us Legal Privacy Policy Terms of Use California Privacy Rights Ad Choices Reprints & Permissions Privacy Preferences Your Privacy Choices Sitemap Charts Music Culture Media Pro Follow Us Follow Billboard on Facebook Follow Billboard on Instagram Follow Billboard on Pinterest Follow Billboard on X Follow Billboard on YouTube Have a Tip? Send us a tip using our anonymous form. Send us a tip Send us a tip The Daily A daily briefing on what matters in the music industry Your email Sign Up Sign Up By providing your information, you agree to our Terms of Use and our Privacy Policy . We use vendors that may also process your information to help provide our services. // This site is protected by reCAPTCHA Enterprise and the Google Privacy Policy and Terms of Service apply. Have a Tip? Send us a tip using our anonymous form. Send us a tip Send us a tip Billboard About Us Accessibility Advertise Shop Events Careers Contact Us Legal Privacy Policy Terms of Use California Privacy Rights Ad Choices Reprints & Permissions Privacy Preferences Your Privacy Choices Sitemap Charts Music Culture Media Pro Subscriptions Customer Service Icon Link PMC Logo Billboard is a part of Penske Media Corporation. © 2025 Billboard Media, LLC. All Rights Reserved. Powered by WordPress.com VIP optional screen reader Our Sites Art in America Artforum Artnews ATX TV ATX TV Festival BGR Billboard BlogHer Deadline Flow Space Footwear News GoldDerby IndieWire LA3C Life is Beautiful Robb Report Rolling Stone SheKnows Soaps Sourcing Journal Sportico Spy StyleCaster The Hollywood Reporter TVLine Variety Vibe WWD Login Login Account Manage Account Log Out Close the menu Charts Expand charts menu All Charts Billboard Hot 100™ Billboard 200™ Global 200 Hits Of The World™ Chart Beat TikTok Billboard Top 50 Songs Of The Summer Song Breaker Year-End Charts Decade-End Charts Music Expand music menu Music News Pop R&B/Hip-Hop Latin Rock Awards Chart Beat Concerts Features Reviews Videos Expand videos menu Culture Expand culture menu Events Lifestyle Politics TV/Film Media Expand media menu Lists Photos Podcasts Videos Business Expand business menu Business News Legal Touring Publishing Radio Record Labels View All Pro Pro Tools Expand pro-tools menu Songwriters & Producers Song Index Artist Index Royalty Calculator Market Watch Industry Events Calendar Billboard Español Expand billboard-espanol menu Noticias Música Negocios Cultura y Entretenimiento Get Up Anthems by Tres Expand get-up-anthems-by-tres menu Honda Music Expand honda-music menu GET ACCESS TODAY Follow Billboard on Facebook Follow Billboard on Instagram Follow Billboard on Pinterest Follow Billboard on X Follow Billboard on YouTube By providing your information, you agree to our Terms of Use and our Privacy Policy . We use vendors that may also process your information to help provide our services. // This site is protected by reCAPTCHA Enterprise and the Google Privacy Policy and Terms of Service apply. About Us Accessibility Advertise Shop Events Careers Contact Us Billboard is a part of Penske Media Corporation. © 2025 Billboard Media, LLC. All Rights Reserved. ad