You might want to spend a few minutes with the following infographic (click on it to see a larger vrsion). Even though it's missing some important fonts like comic sans, it covers a wide variety of fonts. It's drawn from a new book called Just My Type.
Here's more about the book. It sounds like a fun read.
Just My Type is a book of stories about fonts. It examines how Helvetica and Comic Sans took over the world. It explains why we are still influenced by type choices made more than 500 years ago, and why the T in the Beatles logo is longer than the other letters. It profiles the great originators of type, from Baskerville to Zapf, as well as people like Neville Brody who threw out the rulebook. The book is about that pivotal moment when fonts left the world of Letraset and were loaded onto computers, and typefaces became something we realized we all have an opinion about. And beyond all this, the book reveals what may be the very best and worst fonts in the world – and what your choice of font says about you.