Toby Keith Sings “Should’ve Been A Cowboy” In Backseat Of An Uber And The Driver Has No Idea It’s Him [VIDEO]

The Uber driver was completely unaware that his passenger was country superstar Toby Keith and that he was singing his own songs.

By

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 July 15, 2023

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Toby Keith; Photo Courtesy of Krystal Keith on Instagram

Toby Keith‘s daughter Krystal Keith shared a video clip capturing her famous father singing karaoke in the backseat of an Uber on Saturday (July 15). Surprisingly, the Uber driver was completely unaware of Toby’s fame and that he was actually performing his own songs.

“You can’t make this stuff up….” Krystal captioned the clip, before explaining, “We get a cab/Uber to head to @tinrooforlando for an @outdoorchanneltv party during @icastshow with @luck.e.strike and it ends up a karaoke cab…. And the Big Dog takes the stage again 🤣 so fun!”

“Should’ve Been A Cowboy”

The video features Toby Keith singing his chart-topping hit, “Should’ve Been A Cowboy,” while riding as a passenger in an Uber. Toby effortlessly belted the lyrics to his own songs as his daughter and other cohorts laughed as the driver of the Uber was completely unaware of Toby’s superstar status and didn’t recognize him at all.

Krystal also replied to one of her follower’s comments, who asked “Did the Uber know who your dad was and that he was singing his own song?” to which she replied, “no.”

Toby Also Sang “Courtesy Of The Red, White And Blue (The Angry American)”

One day prior, Toby Keith shared a clip from the same Uber ride, where he offered an impromptu karaoke session of another one of his hits.

“This is what happens when my Uber has a karaoke machine,” Keith captioned the clip.

This clip features Toby all smiles belting out the bridge and chorus to “Courtesy Of The Red, White And Blue (The Angry American)” from the backseat of the Uber using a karaoke microphone.

“Cause well put a boot in your ass, it’s the American way / Hey, Uncle Sam put your name at the top of his list / And the Statue of Liberty started getting real pissed / And the eagle will fly and it’s gonna be hell / When you hear Mother Freedom start ringing her bell / And it feels like the whole wide world is raining down on you / Brought to you courtesy of the red, white, and blue / yeah, oh / Of my red, white and blue,” Keith sings in the video.

As he concludes his backseat karaoke session, the other passengers in the car applaud his performance.

Recently Celebrated His 62nd Birthday Earlier This Month

The clip comes just days after Toby Keith rang in his 62nd birthday in style alongside National Fresh Water Fishing Hall of Famer, Jimmy Houston. According to a social media post from Houston, the country superstar indulged in a Mexican dinner at Uncle Julio’s Mexican Restaurant in Orlando, Florida and topped it off with a watermelon raspberry cake.

The photo, shared to Houston’s official Facebook page, finds the Oklahoma native sporting a smile while giving a thumbs up to the camera as he poses in front of his custom watermelon birthday cake that appears to read, “You’re one in a melon.”

Returned To The Stage For The First Time

The country hitmaker and “Oklahoma Breakdown” singer recently returned to the stage for the first time amid his battle with stomach cancer. Keith surprised fans with not just one, but two, surprise, pop-up performances in his home state of Oklahoma earlier this month.

The shows, which took place at his Hollywood Corners venue in Norman, Oklahoma, featured Keith performing alongside a full band and reportedly ran over two hours.

Plans To Return To The Road

These two shows mark Keith’s first official headlining performances since being forced to cancel all of his tour dates in June of 2022 due to his stomach cancer diagnosis.

In a recent interview with The Oklahoman while backstage at the Toby Keith & Friends Golf Classic pre-tournament gala on June 2 at the Riverwind Casino, Keith revealed that he is on the mend and is eager to get back on stage.

“I feel better; I’ve got more wind. And I’m thinking about bringing the band in and setting up, playing two or three days somewhere just to see if I can get through two hours,” Keith continued, “And if I do, (I’ll) be out on the road this fall. All I got to do is see if I can get through two or three nights of work and get a little break in this chemo, and we’ll go back to work. I’m ready.”

Toby Keith first revealed his cancer diagnosis with fans in early June of 2022.

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

Health Update

While chatting with the outlet, the “Oklahoma Breakdown” singer also shared an update on his health, revealing that he is on the mend. 

“I’m feeling pretty good. … I’m about another eight weeks from my last scan. So, I expect next time I look for that tumor to be even less — and I’ve only got one that’s shown up,” Keith explained. “Basically, everything is in a real positive trend. You never know with cancer, so you have to prepare.”

Despite feeling better, Keith is still battling cancer and undergoing chemotherapy. However, his tumor has shrunk by a third and his blood tests continue to improve with each new test.

Toby Keith; Photo Courtesy of Shock Ink/Toby Keith Foundation
Toby Keith; Photo Courtesy of Shock Ink/Toby Keith Foundation

Undergoing Immunotherapy

The Oklahoma-based media outlet also reported that he is also undergoing “immunotherapy and working with a nutritionist.”

“They put oxygen in your blood. They give you high doses of vitamin C and good vitamins and nutrient bag you up to where you feel better. And you can start trying to heal your body,” Toby Keith, who celebrated his 62nd birthday on July 8, added.

“Now, they’re trying to fight where the cancer backs up and says, ‘Oh, you’re fighting that tumor? We’re gonna remorph and turn into this kind of cancer.’ … So, while they (the cancer cells) are in the bullpen regrouping, we’re trying to kill ’em with something different,” he continued.

Toby Keith; Photo Courtesy of Instagram
Toby Keith; Photo Courtesy of Instagram

Touring Plans Remain Unknown

While his touring plans still remain unknown, Toby Keith has made several surprise appearances at different establishments such as Jeff Ruby’s SteakhouseEskimo Joe’s Sports BarThe Noun Hotel, Toby Keith’s I Love This Bar & Grill and more.

Additionally, Toby Keith is filled with optimism as he looks forward to hitting the road again this fall, although there have been no official announcements made yet.

Stay updated by visiting his official website for the latest news and updates.

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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.

See more posts from Andrew Wendowski