Chesney was born on March 26, 1968, in Knoxville, Tennessee.

"If you're going out with someone new
I'm going out with someone too
I won't feel sorry for me, I'm getting drunk
But I'd much rather be somewhere with you"

"I love it," he told People magazine. "Just plain grilled cheese with extra salt. I wrote a song called "Red Wine and Grilled Cheese." I'll put it on a record some day.

Chesney's debut album, In My Wildest Dreams, was released on the independent Capricorn Records label in April 1994. The album's first two singles, "Whatever It Takes" and "The Tin Man", both reached the U.S. Billboard Hot Country Singles & Tracks chart, and the album sold approximately 10,000 copies before Capricorn Records closed its country music division in Nashville later that year and moved to Atlanta.

"She thinks my tractor's sexy
It really turns her on
She's always starin' at me
While I'm chuggin' along"

Chesney and Tim McGraw became involved in a scuffle with police officers in Buffalo, New York, after Chesney attempted to mount a police horse. McGraw came to Chesney's aid when police officers believed the horse was being stolen. The two were arrested and charged, but later acquitted.

Renée Zellweger and Kenny Chesney took the world by surprise when they got married after knowing each other for only five months, but the two decided to have the marriage annulled just four months later. Zellweger cited fraud as the reason in court documents, and after media scrutiny of her use of the word "fraud", she qualified the use of the term, stating that it was "simply legal language and not a reflection of Kenny's character." Chesney later commented, "The only fraud that was committed was me thinking that I knew what it was like ... that I really understood what it was like to be married, and I really didn't."

"A couple years of up all night and a few thousand diapers later
That mistake he thought he made covers up the refrigerator
Oh yeah, he loves that little girl."

Chesney studied advertising at East Tennessee State University in Johnson City, where he was a member of the ETSU Bluegrass Program and the Lambda Chi Alpha fraternity.

"'Cause you and Tequila make me crazy
Run like poison in my blood
One more night could kill me, baby
One is one too many, one more is never enough"