Toby Keith Sings “Should’ve Been A Cowboy” In Uber

Toby Keith Sings “Should’ve Been A Cowboy” In Uber | Classic Country Music | Legendary Stories and Songs Videos

Krystal Keith / Instagram

Toby Keith was filmed singing Toby Keith karaoke during a recent Uber ride!

An unsuspecting Uber driver received a front row seat to an impromptu Toby Keith concert…right in the backseat of his car.  On July 14, Toby took to social media to share a video of him singing Toby Keith karaoke in his Uber.

“This is what happens when my Uber has a karaoke machine,” he captioned the video of him singing “Courtesy Of The Red, White, and Blue” with the windows rolled down and the music blasting.


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A post shared by Toby Keith (@tobykeith)

While we thought the ride was short and sweet, and that Toby only performed that one song, we were so wrong! Toby’s daughter, Krystal, also shared a video – and a story- of the whole situation. She said they grabbed an Uber to go to an Outdoor Channel party at Tin Roof in Orlando and it ended up having a karaoke machine in it! The family was in town because it was ICAST week, which is the largest sportfishing trades how, and Toby recently bought the fishing company Luck E Strike.

RELATED: Toby Keith Acquires Legendary Bait & Tackle Company, Luck E Strike

Krystal shared a video of Toby singing his hit song “Should’ve Been A Cowboy” at the top of his lungs with the windows rolled down. One fan asked, “Did the Uber know who your dad was and that he was singing his own song?” to which Krystal replied, “Nope!”

This is one of the many times Toby has popped up on the scene lately! He made a surprise appearance at his own Hollywood Corners Station in Oklahoma for a 2.5 hours pop-up show two nights in a row.


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A post shared by Toby Keith (@tobykeith)

Toby Keith announced his cancer diagnosis in June 2022 on social media.

“Last fall I was diagnosed with stomach cancer. I’ve spent the last 6 months receiving chemo, radiation and surgery. So far, so good. I need time to breathe, recover and relax,” Toby wrote. “I am looking forward to spending this time with my family. But I will see the fans sooner than later. I can’t wait.”

Looks like he is rarin’ to get back on stage full time!

Watch Toby sing “Should’ve Been A Cowboy” in the back of an Uber below.

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