How to Understand Typography Like a Professional Designer
howtogeek.com
howtogeek.com
But if you're interested in typography, by all means buy "The Elements of Typographic Style" which is a sound and beautiful work on the subject.
All of the great typefaces have some kind of history. An original use case (the brief), influences, designer biography, etc. - which can be looked up on wikipedia or elsewhere. As a general rule, if your project meets the original requirements of the typeface, it should be appropriate. Sometimes a face will pick up additional cultural connotations along the way, depending where it's used. And great graphic designers know when they can mix-and-match history for style.
Making money is probably the specific reason in an awful lot of cases.