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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 then signed with BNA Records, and released his second album All I Need to Know in 1995. "Fall in Love" and the title track both reached the Top 10, while "Grandpa Told Me So" peaked at No. Chesney utilized fiddle and steel instrumentation within this album in order to highlight the down-home sentiments and the unique Tennessee twinge in his voice.In January 2005, Chesney released the album Be as You Are (Songs from an Old Blue Chair), supporting it with his Somewhere in the Sun Tour. The album reached the top of the mainstream of popular music as well as country charts.Although it qualified for platinum status, it seemed a lot less popular than his more traditional albums.He’s a good singer, a good songwriter, and more than anything, I think you’re going to really like him as a person.” "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. 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's first album, In My Wildest Dreams, was released on the independent Capricorn Records label in April 1994.The album's lead-off singles, "Whatever It Takes" and "The Tin Man", both reached the lower regions of the Billboard Hot Country Singles & Tracks charts.