"The Good Stuff" (2002) and "There Goes My Life" (2003–04) are his longest-lasting number ones on the charts at seven weeks each.

The former was also the number one country music song of 2002 according to the Billboard Year-End charts.

Chesney also charted in the Top 10 in mid-2004 as a guest artist on the collaboration "Hey, Good Lookin'".

He has also reached the lower regions of the Hot Country Songs with multiple album cuts, including two charity singles in 1998 and seven cuts from his Christmas album All I Want for Christmas Is a Real Good Tan (including the number 30 title track).

"Beer in Mexico", "Shiftwork" and "I'm Alive" were later released as official singles.