Chesney was born on March 26, 1968, in Knoxville, Tennessee, at St. Mary's Medical Center. He was raised in Luttrell. He is of English and Irish ancestry. 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. Chesney received his first guitar, "The Terminor," for Christmas and began teaching himself to play. Chesney studied advertising at East Tennessee State University in Johnson City, TN, where he was a member of the ETSU Bluegrass Program and the Lambda Chi Alpha fraternity. 