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The album's first two singles, "Whatever It Takes" and "The Tin Man", both reached the lower regions of the U. Chesney then signed with BNA Records, and released his second studio album All I Need to Know from that label 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.This album seemed to capture the traditional spirit that made country music popular.

CMT later recognized the video for the album's title track as the Hottest Video of the Year.2004 saw the release of Chesney's album When the Sun Goes Down.Its lead-off single, "Back In My Arms Again", peaked just outside the Top 40 on the country charts, but the title track (which Chesney recorded on his previous album) and "When I Close My Eyes" (which was previously recorded by Keith Palmer on his 1991 debut album and then by Larry Stewart on his 1993 debut album Down the Road) both peaked at No. Me and You was Chesney's first gold-certified album.A cover of Mac Mc Anally's 1990 single "Back Where I Come From" was also included on this album.This award was presented after Chesney's 2004 Academy of Country Music's Entertainer of the Year award was combined with 1997's New Male Vocalist of the Year award and 2003's Top Male Vocalist of the Year award.

The following year, on May 23, 2006, Chesney was honored with his second Entertainer of the Year at the Academy of Country Music Awards.

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.

He received his first guitar, "The Terminor", for Christmas and began teaching himself how to play it.

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.