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Greatest Hits is the first greatest hits album by Kenny Chesney, released on September 26, 2000 on BNA Records. It features hits from his previous albums, as well as newly recorded tracks. Two of the new tracks — "I Lost It" and "Don't Happen Twice" — were issued as singles. Also released from this album was a re-recording of his 1994 single "The Tin Man". Greatest Hits has been certified 4× Platinum by the RIAA for US shipments of four million copies.
"I Lost It" was the first new release from this album, peaking at number 4 on the Billboard country charts. This song was co-written by Neil Thrasher along with Diamond Rio guitarist Jimmy Olander, and it features uncredited background vocals from Pam Tillis. Following it was "Don't Happen Twice", which in early 2001 became Chesney's fourth Billboard Number One. The third and final release from this album was a re-recording of "The Tin Man", which was previously released as a single in 1994 from his debut album In My Wildest Dreams, peaking at number 70 that year. The re-recording reached its peak of number 19 in mid-2001, and is his last single to miss the top ten. "For the First Time" and "Because of Your Love" are also new to this compilation.
"Baptism", a duet with Randy Travis, was previously included on Chesney's 1999 album Everywhere We Go and Travis' 2000 album Inspirational Journey. This song charted at number 75 in 2000, although Chesney was not credited on it. "Back Where I Come From" is a live cover of a song originally released by Mac McAnally from his 1990 album Simple Life. Chesney previously covered this song on his 1996 album Me and You. "Fall in Love", the first single from his 1995 album All I Need to Know, was re-recorded for the album as well.
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