Toby Keith Surprised Jason Aldean With Concert Appearance

Photo of Toby Keith on stage with Jason Aldean.

Taste of Country / YouTube

Jason Aldean Opens Up About Toby Keith’s Surprise Appearance At His Concert

Country music fans were in for an unforgettable night in Oklahoma on Friday, October 13th, as Jason Aldean took to the stage for what was already promising to be a great show. However, little did the audience know, a surprise guest was going to walk out onto the stage – the legendary “Should’ve Been A Cowboy” singer, Toby Keith.

Jason Aldean Tells The Story Behind The Surprise Appearance

The story behind this surprise appearance goes like this – Aldean, aware of Toby Keith’s prior commitment to go to his grandson’s football game, had his fingers crossed that the iconic artist would make it to the concert. Keith had mentioned that he should be able to return around 10:30pm, but with the show scheduled to end at 11pm, it seemed like a tight squeeze.

Aldean said on a podcast with Taste of Country, “He’s like, ‘I should be back around 10:30. I’m like, ‘the show ends at 11, man.'”

Jason Aldean, who is gearing up for the release of his highly anticipated album, “Highway Desperado” on November 3rd, and Toby Keith, who has been battling stomach cancer since late 2021, were both eager to share the stage with each other once again as legacy country superstars.

Speaking from the heart to podcast host Evan Paul, Aldean said, “It was good to see him in good spirits and doing well. I know he’s gone through a pretty tough couple of years here. You just hate to see that, but you love to see somebody get up and do what they’re so good at and have done for all these years.”

Photo of Toby Keith on stage with Jason Aldean.
Jason Aldean / Facebook

Aldean’s Thoughts Before Toby Showed Up To The Concert

As the night unfolded, it almost seemed like Toby Keith might not make it. But just a few songs before the end of the show, news reached Aldean that Keith had indeed arrived. Aldean said on the podcast that the plan was to make a grand announcement for Toby, but that didn’t go as he imagined.

“I was gonna give him this big announcement, set it up to blow the roof off the place,” Aldean said.

As he was in the middle of building up this massive level of hype and suspense, he saw Toby Keith out of the corner of his eye confidently strutting onto the stage, making the crowd go absolutely nuts.

“I’m in the middle of that and I look over in the pit and people are already going crazy … he’s already walking on stage, just sashaying on stage like he does. Place went crazy.”

Watch Toby Keith’s 1993 “Should’ve Been A Cowboy” Football-Themed Video

After the two performed “Should’ve Been A Cowboy” together, Toby Keith hung around with Jason Aldean and his band, sharing stories and enjoying the good time for several hours. Aldean, who kept tabs on Keith’s battle with cancer, mentioned that he was not surprised to see Keith looking thin due to what he’s had to go through. However, he was very impressed with Toby’s will to fight to get on a path to good health.

“He’s a tough guy. All the things he’s gone through the last couple of years — to still jump and play and still wanna do that — it says a lot about him,” Aldean commented.

For fans awaiting more details about this night, the full interview with Jason Aldean will be available on all podcast platforms and YouTube on November 1st. For now, watch this short 5-minute clip below of Jason Aldean and Evan Paul speaking on the podcast.