Chesney co-directed and produced a film for ESPN entitled The Boys of Fall. He has received six Academy of Country Music awards (including four consecutive Entertainer of the Year awards from 2005 to 2008), as well as six awards from the Country Music Association. He is one of the most popular touring acts in country music, regularly selling out the venues in which he performs. His 2007 Flip-Flop Summer Tour was the highest-grossing country road trip of the year.
The Country Music Association honored Chesney with the Entertainer of the Year award in 2004, 2006, 2007, and 2008. Other notable awards he received include the Academy of Country Music's 1997 New Male Vocalist of the Year, 2002 Top Male Vocalist of the Year, and the Triple Crown Award in 2005. He was awarded his fourth consecutive Entertainer of the Year award from the Academy of Country Music on May 18, 2008.
Chesney was born on March 26, 1968, in Knoxville, Tennessee, at St. Mary's Medical Center and was raised in Luttrell, and is of English and Irish descent. He is the son of David Chesney, a former elementary school teacher, and Karen Chandler, a hair stylist in the Knoxville area. Chesney has one sibling, a younger sister named Jennifer Chandler. In 1986, Chesney graduated from Gibbs High School, where he played baseball and football. He received his first guitar, "The Terminor", for Christmas and began teaching himself how to play it. 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 and graduated in 1990  In 1989, he recorded a self-released demo album at the Classic Recording Studio in Bristol, Virginia. He sold 1,000 copies while performing at the local clubs in Johnson City and used the money from album sales to help himself buy a new guitar. After graduation from East Tennessee State in 1990, he headed to Nashville and performed at several local clubs. He became the resident performer at The Turf, a honky tonk bar in the city's historic district.
In 1992, the head of writer relations at BMI, Clay Bradley, recommended Chesney to his friend, Troy Tomlinson, at Opryland Music Group by saying: "I met this kid today from East Tennessee. He's a good singer, a good songwriter, and more than anything, I think you're going to really like him as a person." Chesney performed five songs during his audition for Tomlinson. Tomlinson's reaction was enthusiastic, later telling HitQuarters:
First of all I was attracted to the songs, because I thought that he painted great pictures in his lyrics, particularly for someone who had not been around the typical Music Row co-writes. I thought that he sang very well too. But more than anything there was a kind of this 'I-will-do-it' look in his eyes - I was really drawn in by the fact that he was so set on being successful in this business.
Chesney left the audition with a songwriter's contract. A year later, an appearance at a songwriter's showcase led to a contract with Capricorn Records, which had recently started a country division.
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 lower regions of the U.S. Billboard Hot Country Singles & Tracks chart. The album sold approximately 10,000 copies before Capricorn Records closed its country music division in Nashville later that year and moved to Atlanta.