The song is about a fellow named Dooley, with whom the singer is in love, who has a rather unconventional lifestyle and a decidedly off-the-beaten-pathway fashion sense; his favorite articles of dress being "tan shoes with pink shoelaces, a polka-dot vest, and a big Panama with a purple hatband."
He takes the young lady "deep sea fishing in a submarine", to "drive-in movies in a limousine" and owns a "whirly-birdy and a 12 foot yacht."
When he feels that war is afoot, he enlists in the armed forces, but gets put into the brig for "raising such a storm" when they "tried to put him in a uniform", preferring to wear his unconventional signature garb.
One day, he feels poorly and decides to write out his will, stating: "Just before the angels come to carry me, I want it down in writin' (sic) how to bury me," requesting to be buried in his preferred attire. The voice heard speaking the line was Randy Van Horne, the founder of the Randy Van Horne Singers who sang the themes from The Flintstones, The Jetsons and many others.