Taylor Swift Reveals Kenny Chesney Once Gifted Her A Life-Changing Surprise Check

“It was for more money than I’d ever seen in my life,” Swift recalls.


Lauren Jo Black

| Posted on

December 6, 2023


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Kenny Chesney, Taylor Swift; Photo Courtesy Facebook

Taylor Swift recalled a kind gesture from country music icon Kenny Chesney in her Time 2023 Person of the Year interview, revealing that he once cut her a check that was worth more money than she had ever come across in her life. 

Swift Booked A Tour With Kenny Chesney When She Was Just 17 Years Old

Reflecting on the early days of her career, when she was chasing her country music dreams, Swift detailed a moment that changed everything for her. She had booked an opening slot on Kenny Chesney’s tour at just 17 years old. At the time, she was a rising singer/songwriter and knew this moment would help elevate her career as Chesney was (and remains) one of the most succesful country music touring artists of all time.

“This was going to change my career,” she told Time. “I was so excited.”

Taylor Swift Time Person of the Year
Taylor Swift Time Person of the Year

She Later Found Out She Wasn’t Allowed To Go On The Tour

In the weeks following, Swift’s dream come true moment came to an abrupt halt. Time reports that she arrived home and saw her mom, Andrea, sitting outside their front door.   

“She was weeping,” Swift recalled. “Her head was in her hands as if there had been a family emergency.” 

That’s the moment Andrea revealed the bad news: Because Taylor was too young and the tour was sponsored by a beer company, she couldn’t join since she wasn’t allowed to be part of a tour associated with alcohol. She was “devastated.” 

Chesney Surprised Her Several Months Later

A few months later while celebrating her 18th birthday, Chesney’s promoter delivered her a card from the superstar himself. 

Kenny Chesney, Taylor Swift; Photo Courtesy Facebook
Kenny Chesney, Taylor Swift; Photo Courtesy Facebook

According to Swift, this card read, “I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you.” 

Much to her surprise, inside the card was a check. 

“It was for more money than I’d ever seen in my life,” Swift recalled. “I was able to pay my band bonuses. I was able to pay for my tour buses. I was able to fuel my dreams.”

Why Did Kenny Chesney Give Taylor Swift Money?

When Time contacted Chesney to get his take on the gift that left Swift speechless, he revealed why he decided to cut her that check. 

“She was a writer who had something to say,” he explained. “That isn’t something you can fake by writing clichés. You can only live it, then write it as real as possible.”

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Swift Surprised Chesney At Bridgestone Arena In 2015

Years later, in 2015, Taylor Swift joined Kenny Chesney on stage at the kickoff of his Big Revival Tour in Nashville. The moment was actually a surprise to Chesney, who happened to be celebrating his birthday that evening. 

“What would birthdays be without surprises? That night, my friend Taylor Swift showed up on my birthday and surprised me,” Chesney recalled in 2017 in a video shared to his Facebook page. “She walked up on stage to sing ‘Big Star’ with me, which is ironic because in a lot of ways, that song and that lyric is Taylor’s journey, in a way. She represented that song so well and sang it so great. It was a really special moment for me and a nice surprise.”   

They Sang “Big Star”

The live recording of “Big Star” featuring Kenny Chesney and Taylor Swift is featured on Chesney’s Live In No Shoes Nation. This project is the East Tennessee native’s second live album and was released on October 27, 2017. 

Taylor Swift was named Time’s 2023 Person of the Year. She currently graces the cover of the publication, and inside she opens up about her life on tour, her personal life, and more.

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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 Answers.com and her work being featured on Forbes.com. 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.