Storytelling and connection are two of the hallmarks of a Kenny Chesney show.
For over three decades, the singer’s been honing his communication skills with his audience. He’s a master at connecting with the fan in the nosebleeds, just as easily as he can connect with the fan in the front row.
But that skill took time, and his songs haven’t always landed quite as a powerfully as he intended.
During a new episode of CBS Sunday Morning, while in conversation about his new book Heart Life Music, Chesney recalled an early-career incident where a song he wrote failed to have the desired effect.
This was back when Chesney was in college at East Tennessee State University, and he had a crush on a girl in his Persuasion class.
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“She sat right beside me. I tried, I mean, it was six months trying to get her to go out with me,” Chesney recounted. “…I’m like, ‘Okay, I’m gonna write her a song.'”
At the time, he had just started playing shows at local bars and was beginning to think about writing his own material.
“This was the first song I ever wrote, and it was trying to persuade — and ironically enough, it was in a class called Persuasion,” he continues.
He wrote the song, recorded it onto a cassette and passed it to the girl on a Thursday. Then, he had to wait all weekend until the class met again the following Tuesday. He walked in that day full of anticipation.
“I came in, like, ‘Okay, this is it,'” Chesney says. “She was sitting as far back in the corner of the room as she could sit.”
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Needless to say, that relationship didn’t work out.
But the experience was an important lesson in connecting with an audience — something that would arguably go on to become the most prominent part of Chesney’s country music career.
“That was my first taste of rejection in the music business, and as a songwriter,” he explains. “But it went from there, yeah. You listen, you read, you observe people’s lives and you try to communicate that.”
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Gallery Credit: Billy Dukes

