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.”


Lauren Jo Black

| Posted on

October 14, 2023


9:05 am

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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. 

Toby Keith; Photo Courtesy Suzanne Cordeiro
Toby Keith; Photo Courtesy Suzanne Cordeiro

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.”

Toby Keith; Photo by: Todd Williamson/NBC
Toby Keith; Photo by: Todd Williamson/NBC

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.”

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Lauren Jo Black

Written by

Lauren Jo Black

Lauren Jo Black, a University of Central Florida graduate, has immersed herself in the world of country music for over 15 years. In 2008, she co-founded CountryMusicIsLove, eventually selling it to a major record label in 2015. Following the rebranding of the website to Sounds Like Nashville, Black served as Editor-in-Chief for two and a half years. Currently, she assumes the role of Editor-in-Chief at Country Now and oversees Country Now’s content and digital footprint. Her extensive experience also encompasses her previous role as a Country Music Expert Writer for and her work being featured on She’s been spotlighted among Country Aircheck’s Women of Influence and received the 2012 Rising Star Award from the University of Central Florida. Black also spent time in front of the camera as host of Country Now Live, which brought live music directly to fans in 2021 when the majority of concerts were halted due to the pandemic. During this time, she hosted 24 weeks of live concerts via Country Now Live on Twitch with special guests such as Lady A, Dierks Bentley, Jordan Davis, Brett Young, and Jon Pardi. Over the course of her career, she has had the privilege of conducting interviews with some of the industry’s most prominent stars, including Reba McEntire, Blake Shelton, Luke Combs, Carrie Underwood, Luke Bryan, Miranda Lambert, Lainey Wilson, and many others. Lauren Jo Black is a longtime member of the Country Music Association and the Academy of Country Music.