Kenny Chesney Praises Taylor Swift: ‘I’m So Proud Of You and I Love You’

Taylor Swift has just been named the TIME Person of the Year, and no one is prouder of her than Kenny Chesney. The 55-year-old penned a touching tribute to Swift, sharing a couple of throwback photos of Swift early in her career.

“Taylor, I knew looking in your eyes that first time onstage with us, you had ‘it,'” Chesney wrote. “The hunger, that something special… A gift not everyone has to connect. It’s been awesome watching you shine! Congratulations on being TIME’s Person of the Year. I’m glad TIME sees what I’ve always loved about your music, your art and you as a human being. I’m so proud of you and I love you.”

Taylor, I knew looking in your eyes that first time onstage with us, you had “it.” The hunger, that something special… A…

Posted by Kenny Chesney on Wednesday, December 6, 2023


Chesney’s friendship with Swift goes back to the beginning of Swift’s career. When she was just 17 years old, she was invited to open for Chesney on tour — a guaranteed career-booster, and a big one. Unfortunately, the tour was being sponsored by a beer company, which meant Swift’s age prohibited her from being part of the tour. It’s a disappointment Swift still remembers, even after all these years, in vivid detail, coming home to find her mother, Andrea, weeping on the front steps.

“Her head was in her hands as if there had been a family emergency,” Swift tells TIME, adding that her mother was sobbing as she told Swift she couldn’t join Chesney on tour.

“I was devastated,” Swift remembers.

Chesney had to find a new opening act, but he well understood the disappointment Swift faced, and went above and beyond to make it right for the teenager, giving her a birthday card with a life-changing amount of money inside.

“I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you,” Swift recalls Chesney writing. “It was for more money than I’d ever seen in my life. I was able to pay my band bonuses. I was able to pay for my tour buses. I was able to fuel my dreams.”

Dreams indeed. Her global The Eras Tour, which will extend into 2024, has set records all over the world for ticket sales. Once a country music singer, Swift’s reign has extended into rock, pop and more, making her one of the biggest — if not the biggest — artists of this generation.

Chesney may not be the TIME Person of the Year, but his career remains at an all-time high as well. He recently added an unprecedented third show to Gillette Stadium, to close out his 2024 Sun Goes Down Tour. Find music and tour dates at