I don't write songs, but JtS does. He gets his inspirations in some interesting ways.
The inspiration for one of his best and funniest songs, "Pasties and Thongs", happened this way...
The husband of one of the members of some political body in Columbus, Georgia, left her and ran off with a stripper. So she arranged somehow to get a law passed requiring that strip joints in Columbus couldn't serve alcohol and have naked strippers dancing at the same time. If alcohol was being served, the dancers had to wear pasties and thongs.
Another interesting and amusing inspiration was a week long song workshop he took at the Kerrville Folk Festival. The actor, Ronnie Cox (Deliverance, Beverly Hills Cop, etc.), was also participating in the workshop. Mr. Cox had written a song about traveling around with some guy named "Jack", and he sang the, as yet, not quite finished song to the other participants.
JtS wrote a parody of Cox's song and at the workshop the next day, sitting right next to Cox, JtS sang the parody. It was called "I don't know Jack".