Country music legend Kenny Chesney is in the process of promoting his new book, “Heart Life Music.” Naturally, he discusses his legendary career in the memoir, but he also details how Taylor Swift was almost his opening act on tour. Recently, he shared how he knew early on that she was a special artist.
Chesney spoke to PEOPLE about the new book, as well as what he saw in Swift early in her career. The “No Shoes, No Shirt, No Problem” singer said, “With Taylor, I mean, she had the eye of the tiger even as a teenager.”
He continued, ” And I recognized that early on. You can’t look into a crystal ball [to] predict and see what happened to her, but I could tell that she was really talented and really wanted it. And even at a young age, she was a really good songwriter. So I knew something special was going to happen there.”
Chesney Had Selected Swift to Open for His 2007 Tour
It’s typically a right of passage for up-and-coming artists to open on tour for more established acts. It’s for this reason that it was such a big deal that Chesney asked Swift to open for his 2007 “Flip-Flop Summer Tour.” Sadly, this didn’t come to be.
Swift revealed in her 2023 Time Person of the Year interview that she could not be included on the tour as a beer company sponsored it. She recalled her mother breaking the news to her that she wouldn’t be able to tour with the country music legend.
Swift told the outlet, “She was weeping. Her head was in her hands as if there had been a family emergency.” Regarding how she felt, the “Shake it Off Singer” said, “I was devastated.” Still, Swift also said that Chesney later gifted her a card for her 18th birthday. It included a kind note and more money than she’d ever encountered.
Since then, they’ve both been supportive of one another.
His New Book Comes out in November
Chesney announced “Heart Life Music” in February 2025. The singer spoke to CBS Mornings about the process of writing it. He said, “For the first time, I get to share with my audience and the world a lot of very unique stories of my life in the music business, and I’m thrilled about that.”
He continued, “It’s not every day that you get to meet a lot of your heroes, and I got to not only meet them, I got to collaborate with them. I got to share life stories with them. I got to go on the road with some of them. A lot of those intimate details are in this book.”
“Heart Life Music” will be released on November 4.
