WATCH: Country Icon Toby Keith Pops Up At Jason Aldean’s Oklahoma Concert For Surprise Duet
Aldean was thrilled to share the stage with the true “legend.”

Jason Aldean, Toby Keith; Photos by Justin Mrusek, Courtesy Facebook
Toby Keith made a surprise appearance at Jason Aldean’s concert in Oklahoma City, Oklahoma on Friday evening, and the pair joined forces for a collaborative performance of Keith’s breakout hit, “Should’ve Been a Cowboy.”
The ‘Big Dawg Daddy’
Aldean shocked concert attendees when he announced the recent Country Icon Award recipient to the stage. “There’s only one guy that you kinda think of when you come to Oklahoma City….make some noise for the Big Dawg Daddy, Toby Keith!”
Cheers and applause erupted as Toby Keith joined Jason Aldean on stage.
@kym.adams Toby Keith at the Jason Aldean concert #jasonaldean #jasonaldeanconcert #fyp #tobykeith #counteymusic #oklahoma ♬ original sound – Kym
“I’m on my rehab tour,” Keith joked. “If I’m not at my bar, I’m down at Hollywood Corners or I’m on stage with Jason Aldean. The Almighty’s been riding shotgun and my ass is ready to get back to work!”
Together, the country stars teamed up to sing Keith’s 1991 chart-topper, which was written solely by Toby Keith and kick-started his wildly successful career.
“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,” they sang as fans around the arena watched on, many with their cell phones held high, capturing the memorable moment on video.
“Should’ve Been A Cowboy” Duet
@taliarenee27 @Jason Aldean was fantastic tonight!! He brought out Toby Keith tonight, which is a must in Oklahoma! #TryThatInAsmallTown #Okc #fyp #JasonAldean ♬ original sound – Nattyd27
On Saturday morning, Aldean shared several photos from his Friday night concert and reflected on the extraordinary evening.
“Brought The House Down”
“Sometimes you just have one of those special nights that you will never forget. I had one of those tonight in Oklahoma City,” the Georgia native wrote. “Thank you to a true ——- legend Toby Keith for coming out tonite. Mad respect and u brought the house down big Dawg!”
In recent months, Keith has made several rare public appearances. Just last month, he appeared at the People’s Choice Country Awards for his first major awards show performance in six years. After accepting the Country Icon Award from Blake Shelton, Keith stunned viewers with an emotional performance of his song “Don’t Let The Old Man In.”
Chart Resurgence
Sales of the song continued to surge following the buzzed-about performance. According to a recent press release, the song topped Billboard’s Country Digital Song Sales chart for the second consecutive week. Additionally, the poignant tune placed in the Top 3 on the all-genre sales chart.
As the song continues its resurgence, fans are anxiously awaiting Keith’s return to the stage following his battle with stomach cancer. He previously canceled all of his 2022 tour dates in order to undergo treatment, however, this summer, he made his return to the stage with two surprise performances in his home state of Oklahoma.

He performed for over two hours at his Hollywood Corners venue in Norman, Oklahoma in July. , “Toby‘s first rehearsal turned into a 2 1/2 hour pop-up show. He sang all the hits plus the Bus Songs…Toby is back,” a post to his official social media accounts read.
Most recently, Keith gave an update on his health during an interview with E! News.
“I feel pretty good,” Keith shared on the red carpet at the PCCAs. “It’s a little bit of a roller coaster. You get good days and, you know, you’re up and down, up and gown. It’s always zero to 60 and 60 to zero but I feel good today.”

New Project Coming Soon
The 62-year-old will soon release a new project, dubbed 100% Songwriter, on November 3. The 13-track collection celebrates Keith’s most legendary solo-written songs, all assembled into one collection.
Among the track list is Keith’s breakout hit, “Should’ve Been A Cowboy,” which was just certified triple platinum from the Recording Industry Association of America (RIAA). Released in 1993, the song marked the beginning of a wildly successful career for the Oklahoma native, which went on to include 52 top 10 hits, 32 No. 1s, more than 40 million albums sold, 100 million airplay performances (BMI) and more than 10 billion streams.
Other notable tracks included on 100% Songwriter include fan-favorites such as “He Ain’t Worth Missin’,” Wish I Didn’t Know Now,” and “Big Ol’ Truck.”
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.







