- "He Stopped Loving Her Today" is one of the saddest songs in country music, which is really saying something.
- "Choices" is sung from the perspective of a man who has ruined his life through alcohol addiction, and begins to realize this his predicament is his own doing. Simply put, it is a heartrending tearjerker of a song about how we all must live with the consequences of the decisions we make in life, a sentiment that seems especially credible coming from a reformed hellraiser like George.
- Fans consider "Choices" to be the equal of any of his classic hits, and certainly the best of the late phase of his career. So it's pretty sad that he was relegated to a minor appearance at an awards show to perform a truncated version. It bothered him so much that he eventually refused to do it at all. Although it did lead to a heartwarming moment when Alan Jackson sacrificed some of his own song on the show to perform "Choices" in honor of Jones and in protest of his treatment.
- The narrator of "If Drinkin' Don't Kill Me (Her Memory Will)" is on the verge of drinking himself to death after realizing that he will never overcome the pain associated with his ex's memory.
- The narrator of "The Grand Tour" takes his listener on a tour of his house, only for the listener to suspect something is amiss and for the narrator to reveal the truth in the startling climax.
- "Who's Gonna Fill Their Shoes?" mourns the fact that the legends of country music are one-of-a-kind and irreplaceable.
- His duet with Tammy Wynette, "Golden Ring", is a devastating account of a man and woman from engagement to marriage to divorce. Jones and Wynette being freshly divorced themselves when they recorded it just adds more layers of sadness to the song.
Tear Jerker / George Jones