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.

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.”

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.

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.”
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.
Lauren Jo Black is a longtime country music journalist, editor, host, and media personality whose work has helped shape the conversation around country music for nearly two decades. As the current Editor-in-Chief of Country Now, she has become one of the genre’s most respected voices, interviewing hundreds of country music’s biggest stars, including Dolly Parton, Garth Brooks, Reba McEntire, Shania Twain, Randy Travis, Luke Bryan, Carrie Underwood, Blake Shelton, Luke Combs, and countless others. Over the course of her career, Black’s written work and interviews have reached billions of country music fans worldwide. A 2009 graduate of the University of Central Florida, Black began her career by founding Country Music Is Love, one of country music’s earliest independent digital publications, which she later sold to a major record label in 2015 before it was rebranded as Sounds Like Nashville. She then served as the publication’s Editor-in-Chief for more than two years. Her work has also appeared in Forbes, and she previously served as the Country Music Expert for Answers.com. Widely recognized for her expertise, Black has appeared as a featured guest on The Bobby Bones Show, BobbyCast, and Scripps News Morning Rush, providing insight on country music’s biggest moments. She has also hosted Country Now Live, a concert series featuring performances from artists including Lady A, Dierks Bentley, Riley Green, Jordan Davis, Dustin Lynch, Gabby Barrett, Brett Young, Jon Pardi, Kip Moore, Chris Young, and more. The series has welcomed thousands of fans in person while reaching millions more online. In addition, she hosted Connect With Country Now, a weekly interview series featuring conversations with rising country stars. Throughout her career, Black has earned a reputation for discovering and championing artists long before they become household names. She has covered Luke Bryan since the early days of his career, beginning when he was writing songs for other artists, including Billy Currington’s No. 1 hit “Good Directions,” before stepping into the spotlight with his debut single, “All My Friends Say” and eventually becoming one of biggest names in music. She also gave Megan Moroney her first opportunity to walk a major red carpet as Country Now’s official guest correspondent at the 2022 CMA Awards. An interview she conducted in 2018 for Forbes.com with Luke Combs that inspired his multi-week No. 1 hit, “Doin’ This.” She has also hosted stages at CMA Fest, moderated an industry panel at Country Radio Seminar, and helped lead important conversations about the evolving landscape of country music media. Beyond journalism, Black has also used her platform to support charitable causes and highlight organizations making an impact. Through Country Now Live, she has helped raise awareness and support for St. Jude Children’s Research Hospital, while also advocating for animal rescue through Country Now’s Pupdate series, spotlighting organizations including MuttNation Foundation, Wags & Walks, and Proverbs 12:10 Animal Rescue. Black has been recognized as one of Country Aircheck’s Women of Influence and received the 2012 Rising Star Award from the University of Central Florida. She is a longtime member of both the Country Music Association (CMA) and the Academy of Country Music (ACM). After nearly 20 years covering country music, Lauren Jo Black has spent her career telling the stories behind the artists, songs, and moments that have shaped the genre. Her first-ever book, Country Music Forever: An A-to-Z Celebration of Icons, Songs and Stories, brings that same passion and firsthand knowledge to the page, celebrating not only the legendary artists and timeless songs that have become the soundtrack to generations of fans, but also the places, traditions, and cultural moments that have made country music one of the most beloved genres around the world.









