Well, Robert Bringhurst's The Elements of Typographic Style is an extraordinary book about typography. However, he has his own classification system that is based more on art history terms than the "standard" oldstyle-transitional-modern classification. It's an interesting way of thinking about typefaces but if you use his terms most people won't know what you're talking about.

Here are a few links that might be helpful...

http://www.amazon.com/typography-recommended-Hoefler-Tobias-Frere-Jones/...

http://www.creativepro.com/blog/typetalk-top-ten-type-resources-online

Some of my favorite type history books:

(I've omitted ones that are on the Hoefler and Frere-Jones list, which is very useful on its own.)

"A Short History of the Printed Word" — Warren Chappel / Robert Bringhurst (second edition)
This is a wonderful overview of general typographic history

"Type: The Secret History of Letters" — Simon Loxley
While not a formal type history, this is a wonderful collection of anecdotes about specific designers and faces

"Meggs' History of Graphic Design" — Philip B. Meggs / Alston W. Purvis (fourth edition)
This comprehensive textbook covers all aspects of graphic design history, not just typography

Incidentally, I think the Bringhurst classifications (Renaissance/Baroque/Neoclassical/Romantic/Rococo/Modern/Postmodern etc) are much more useful in talking about type history than oldstyle/transitional/modern, which I couldn't even define off the top of my head. How "old" is oldstyle? If we say Renaissance, though, everyone knows when the (Venetian) Renaissance was, and what was going on in related arts. The distinctions seem to also be finer than the conventional system allows for. Mugford is right, though; Bringhurst's terms aren't often used by typographers (or taught in school), at least in my experience.

Do you know of any good books that are more about the history of letterforms way way back? Like the progression to how we even came to have the forms that we have now? (e.g. Egyptian, Greek, ancient letterforms) I am going to buy a couple of the books you guys suggested but I am also interested in that sort of history, which seems to be more difficult to come by..

> "Do you know of any good books that are more about the history of letterforms way way back? Like the progression to how we even came to have the forms that we have now?"

I absolutely do! Read "Mysteries of the Alphabet" by Marc-Alain Ouaknin (translated by Josephine Bacon).

The Ouaknin book sound interesting.

Also good on letterforms is 'The Alphabetic Labyrinth' by Johanna Drucker, available in paperback ( largesize - about 7.5 " x 10.25") paperback is also very good.

A classic history of typefaces up to the 1920s is 'Printing Types: Their History, Forms and Use', by Daniel Berkely Updike, in 2 volumes. It's a great foundation for a typographical library. It was reprinted by the Harvard U. Press in 1951.