Barbara Nicolosi has a post on sad songs. The post is based on an article in the Guardian in which the author runs through a list of what he says are the saddest songs out there. Yeah, he skimps on some genres, but the main problem is that he seems to focus on bad sad songs - (Earworm: We had joy, we had fun, we had seasons in the sun!).
For your consideration, what I think is one of the saddest songs ever, and it's a good song, too:
Everything that Glitters is Not Gold by Dan Seals. Oh my word, the first time I heard this, I was driving home from somewhere late at night, it came up on the radio, I'd never heard it before, and boy there was I was on 92 coming into Lakeland, dern tears just streaming down my face. Good Lord. Talk about sad.
He has one Harry Chapin song on there, but really, which of his songs is authentically, truly sadder than Cat's in the Cradle?
I also like what Barbara has to say about the kinds of music you fill your house with...