Chesney's version is the first single from his album Lucky Old Sun, which was released on his own Blue Chair label in association with BNA Records.

[5] Chesney's rendition of the song is a mid-tempo, set in a calypso orchestration[2] with a slight reggae feel, and is backed by The Wailers, who also sing the final chorus on the album version.

The song is about a man detailing his life to a preacher who has told him to forgo a lifestyle of drinking alcohol and pursuing sexual desires, in favor of a more religious-oriented style.

Although his review makes note of the song's "carefree sentiment that characterizes standards like 'Live Fast, Love Hard, Die Young'", he considered the calypso orchestration "patently offensive".

Although she referred to the instrumentation as "not-so-country", she described the song's sentiment favorably, comparing it to Tim McGraw's 2004 single "Live Like You Were Dying", but without a "preachy feel".