In a recent interview, country singer Jake Owen opened up about what he admires most about Kenny Chesney — and it’s not the sold-out stadiums or the endless summer tours that made Chesney the “King of the Road.” What truly impresses Jake is how Kenny always seems to do everything right — both on stage and in life.
“I opened for Kenny on his Trip Around the Sun Tour,” Jake recalled. “When you watch how he treats his crew, his fans, even the stagehands after the show — you understand why he’s still on top. He never phones it in. Everything he does comes from a real love for music.”
According to Jake, Chesney’s success comes down to two things: discipline and gratitude. Despite being one of the biggest country stars of all time, with hits like “When the Sun Goes Down,” “The Good Stuff,” and “There Goes My Life,” Chesney maintains a rigorous routine — from vocal warm-ups to detailed sound checks — and always thanks his team personally after each show. “He’s the first to arrive and the last to leave,” Jake said. “Everything feels planned, but somehow, it never loses its heart.”
Kenny himself once said, “Every time I walk on stage, I think about the people who drove hours, who bought tickets months ago, just to spend one night with my music. I owe them my best.” That mindset has kept his fan base fiercely loyal for decades, even as country music evolved through countless trends.
Jake Owen also emphasized that Kenny’s “rightness” extends beyond his career. “He never lets fame change him. He knows who his real friends are. He chooses peace over noise.” Jake admitted that he’s learned from Kenny how to stay genuine — something rare in the entertainment business.
When asked what makes Chesney truly stand out, Jake didn’t hesitate: “He understands that music is just one part of life — real happiness comes from living fully.” At 57, Kenny Chesney remains fit, vibrant, and grounded. He spends much of his time in St. John, writing songs, exercising, and living a quiet island life away from the spotlight.
Kenny’s career is proof that balance and authenticity never go out of style. No scandals, no gimmicks — just honest music and hard work. And for Jake Owen, that’s the most powerful lesson: “Do the right thing, your way, every day.”
Jake ended the conversation with a smile: “I used to think success was when you’re performing in front of thousands. But Kenny taught me that real success is when you can still recognize yourself after the lights go down.”