The first one that came to mind was Paul Simon's Dangling Conversation, but I think "Sounds of Silence" and "Mrs Robinson" would also fit in this category.

And then there's Norman Normal written by Noel Paul Stookey and recorded by Peter, Paul, and Mary.

I suppose it's not exactly in this category, but Foolish Questions (Arthur Smith) could be stretched to fit - and it's such a good song.

-Joe-