His annual income is estimated to be around .0 million.
He has received six Academy of Country Music awards (including four consecutive Entertainer of the Year awards from 2005 to 2008), 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.“Merry Christmas from Blue Chair Bay,” he captioned a pic of him on the beach with a blue chair, a reference to his rum company. He also received the Pinnacle Award during the CMAs.Kenny and actress Renée Zellweger met each other in January 2005 during a tsunami relief event.
After merely four months of dating, the pair decided to get married.He studied advertising from East Tennessee State University, where he would occasionally play gigs at local bars. He used to perform in local pubs and sold almost 1,000 copies of the album.The money made from the sale was used to buy a new guitar.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, In 1992, the head of writer relations at BMI, Clay Bradley, recommended Chesney to his friend at Opryland Music Group, Troy Tomlinson, by saying: "I met this kid today from East Tennessee.Upon completing his degree, he moved to Nashville to further pursue his dreaming of becoming a country singer. His passion for music is seen in every song he performs.