Kenny Chesney may be one of the biggest names in country music today, but he admits it didn’t start out that way. In fact, in the early days of his career, he almost lost himself by trying too hard to be someone else — none other than George Strait.
And honestly, who can blame him? George is The King of Country. Most young artists would be thrilled with even a fraction of his success. But as Chesney learned, there’s only one George Strait — and chasing that shadow nearly cost him his own identity.
In a 2023 interview with Country Countdown USA’s Lon Helton at the Country Radio Seminar, Chesney opened up about that early struggle:
“I was like a lot of artists, honestly. I was trying to be the newer version of George Strait… I wore the belt buckle. I was trying to be that.”
But the more he leaned into the imitation, the more he realized he was blending in instead of standing out. Other artists were doing the exact same thing, and Chesney admits he wasn’t delivering songs as strong as what his peers were putting out at the time.
“We were all reaching for Strait. I just felt I wasn’t being authentic as an artist during that time… There was a phase, after Garth hit, where everybody wore the same shirt.”
The turning point came when he stopped chasing George Strait’s image and started leaning into his own. He began writing songs that reflected his life and experiences — many of which came during his time spent in the Virgin Islands. From that moment, his career completely shifted.
And yet, even with all the lessons learned, Chesney still second-guessed himself at times. He confessed that when “Don’t Blink” was chosen as a single in 2007, he hated it at first:
“When we released that song… I hated it. I felt like it just touched every button you could possibly touch to get somebody to like a song. I thought, ‘This is the end of everything.’”
But, of course, fans had the final say. “Don’t Blink” became a four-week #1 hit on the Billboard country airplay chart and is still one of Chesney’s most beloved songs nearly two decades later.
Looking back, it’s clear that letting go of imitation and embracing authenticity was the key to Chesney’s longevity. His story is proof that even legends like George Strait can inspire — but true success comes only when you find your own voice.
