Greatest Hits (Kenny Chesney album)

"I Lost It" was the first new release from this album, peaking at number three 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.

"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 remixed for the album as well.

MTV's music journalist Chet Flippo criticized the compilation album as a result of "mainstream Nashville labels and their major artists" concentrating on songs that fit the "radio and retail" ideals and push "artistic achievement" out, despite Chesney's talent and "pleasant voice". Flippo praised "That's Why I'm Here" and "Baptism" but panned "She Thinks My Tractor's Sexy", "How Forever Feels", and one of the album's four new songs "I Lost It", which he called "forgettable".^[2]