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He was also presented with AMA's 2004 Artist of the Year award.

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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.

The album's title track, a duet with Uncle Kracker, was also a No. The video from the third single from the album, "I Go Back", was honored on April 11, 2005 with the Male Video of the Year Award from Country Music Television.

This song, along with the album's fourth single "The Woman with You", entered the Top 5 both with a peak at No. The fifth single "Anything But Mine" reached number one while the final single "Keg in the Closet" went to No. When the Sun Goes Down was honored with the 2004 CMA award for Album of the Year while Chesney was honored as the Entertainer of the Year.

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.