You can spend your whole life obsessing over type. It’s a craft with an awesome history and practicing it well often takes designers on a sort of quest that never seems to end. The strategies are both infinitely complex and sometimes irreducibly simple. The following resources are comprised of some of my favorite articles on the subject and some sites that should give most a great head start.
Web Typography Tutorial - Oldie but goodie from the Webmonkey era. Nadav Savio does a fantastic job introducing history, importance and vocabulary of web typography.
The World of Fonts - A history lesson on fontography. If you want to talk intelligently about this craft, you have to understand the roots that brought us here.
The Trouble With EM ‘n EN (and Other Shady Characters - I love this article. It’s from A List Apart and it’s about using proper typographic punctuation.
I Hate ITC Garamond - This is how you hate a font. It’s much better than saying, “Dude, that’s gay.”
Typetester - A great Ajax tool to help you compare and see in real time your typography decisions. Lots of great links in this one.
Typographica - Undisputed blog champion for your typographic news. Smart writing, great content.
25 Best License-Free Quality Fonts - This has been making the rounds and it’s an unstoppable resource. Click on all the links in that first paragraph. They all kick ass.
Linotype FontExplorer X - Linotype’s new tool has received a lot of praise for their new font management tool. I haven’t used it myself, but font management is key for successfully handling your typography arsenal.