Kenny Chesney recognized Taylor Swift’s talent early on when she was just a teenager slated to open for him on his 2007 Flip-Flop Summer Tour. Swift ultimately had to be removed from the lineup due to an alcohol sponsorship that prevented the underage artist from joining the tour, leading Chesney to compensate her with a check and a heartfelt note to make up for missing the shows. In his upcoming book, Heart Life Music (out Tuesday, Nov. 4), Chesney reflects on Swift’s creative drive and songwriting skills. “With Taylor, I mean, she had the eye of the tiger even as a teenager. And I recognized that early on,” Chesney recalls. “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 launched his 10-stop book tour on November 1 in Johnson City, Tennessee. (People)
Getty Images
Kenny Chesney Recalls That He “Could Tell” Former Opener Taylor Swift Was “Special,” Even As A Teenager
By Erik Thompson
Nov 2, 2025 | 6:01 PM
Last Played
More
Trending
Gorillaz Bring 'The Mountain' to Studio 8H for Milestone SNL Set
10h ago
CyHi Reflects on G.O.O.D. Music Legacy in New Single 'The G.O.O.D. Ole Days'
10h ago
How Blackpink's Lisa and Viral Monkey Punch Captivated Social Media This Weekend
10h ago
How Ben Gallaher Turned a 2022 Ballad into a Country-Rock Hit
4h ago
Country Joe McDonald, Iconic Woodstock Protest Singer and Activist, Dies at 84
10h ago
Last Played
More
Trending
Gorillaz Bring 'The Mountain' to Studio 8H for Milestone SNL Set
10h ago
CyHi Reflects on G.O.O.D. Music Legacy in New Single 'The G.O.O.D. Ole Days'
10h ago
How Blackpink's Lisa and Viral Monkey Punch Captivated Social Media This Weekend
10h ago
How Ben Gallaher Turned a 2022 Ballad into a Country-Rock Hit
4h ago
Country Joe McDonald, Iconic Woodstock Protest Singer and Activist, Dies at 84
10h ago

