Kenny Chesney’s Complicated Relationship With His Smash Hit “She Thinks My Tractor’s Sexy”

The veteran country musician, Kenny Chesney, has been around to see it all. And thanks to his tenured career in country music, his career has seen it all. Chesney’s career has had its peaks and valleys, although, he remains a country music great due to songs such as “American Kids” and “Summertime.” However, Chesney’s biggest hit and the one that song launched him into superstardom, is the one he has the most troubled relationship with.

There have numerous occasions in which Chesney publicly addresses his relationship with “She Thinks My Tractor’s Sexy.” In each address, Chesney articulates how the overly cliche song lacks things that great country songs consist of. Nevertheless, the song continues to acquire Chesney buckets of success 25 years after its release in 1999.

Kenny Chesney’s 60 Minutes Interview

In 2007, Chesney sat down with Anderson Cooper to discuss his massive success due to his incredibly marketable appeal. That being so, one of the focal points of the conversation was one of Chesney’s most successful hits of all time. In addition to acknowledging the silliness of the song, Chesney also told Cooper, “There was no gray area with that song. Either you loved it or you hated it. You know what I mean? But it was a great groove.”

Further attesting to the polarity of the song, Chesney also said, “I was smart enough to record that song but I was smart enough also not to record another one.” Per these two comments, Chesney knows how ridiculous the song is. Hence, he said he’d never do another one like it again. However, he knows it’s what got him his start and he’s thankful for it.

Talking It off the Tour

In a recent interview on The Pat McAfee Show, Chesney divulged why he took the song off the setlist of his 2024 tour. Even though Chesney seemingly has a complicated relationship with the song due to its quality and subject matter, his main reason for its departure was that he just “got so sick of singing it.” And given that Chesney has headlined 16 tours, his answer is more than sufficient.

Despite Chesney’s disdain for the song’s musical caliber and his oversinging of it, he knows it’s a crowd favorite. He knows it’s what helped make him famous, and he “knew that a lot of people that grew up just like [he] did would go crazy over it,” per 60 Minutes. That being so, Chesney saw an opportunity and made a song he didn’t necessarily like, so he could go on to make the ones he loves.

Photo by Terry Wyatt/Getty Images

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