Jason Aldean And “Legend” Toby Keith Bring Down The House With Surprise Duet In Oklahoma

“Sometimes you just have one of those special nights that you will never forget. I had one of those tonight in Oklahoma City,” Aldean wrote.

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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 October 14, 2023

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Jason Aldean, Toby Keith; Photo Courtesy of Lydia Reading/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.”  

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.

Watch Jason Aldean And Toby Keith Sing A Duet Together Below

@batmanda_lucy

So happy to see @Toby Keith on stage again! Brought back all those core memories ❤️💙

♬ original sound – Batmanda

“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!” 

Jason Aldean, Toby Keith; Photo Courtesy of Justin Mrusek
Jason Aldean, Toby Keith; Photo Courtesy of Justin Mrusek

Performed “Should’ve Been A Cowboy”

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. 

On Saturday morning, Aldean shared several photos from his Friday night (Oct. 13) concert and reflected on the extraordinary evening.  

“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!” 

“Don’t Let The Old Man In” Sales Surge

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.” 

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. 

Keith 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. 

Update On His Health

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 Courtesy of Allen Clark/NBC
Toby Keith; Photo Courtesy of Allen Clark/NBC

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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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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