Okay, so my closest friends know that I have been a Fontaholic for many years.
Here are some links to my favorite font sites. Most feature FREE fonts, but a few are pay sites (but well-worth giving your money to...)

House Industries: The BEST, coolest and hottest original retro fonts ever! True, they ain't cheap, but these are CLASS. There are a few free fonts to grab, but most everything here costs $$. Worth it. Made in Delaware.
Font Diner: My second favorite retro font site. All-original font designs that are top-notch. Check out their free fonts, but like House, they save the really good stuff for exchange of your money.
Blambot Fonts: Great Comic Book fonts, both free and pay versions. Made in Rhode Island, USA.
Fontalicious: Groovy original FREE fonts in a cool retro (mostly '60s) style. Out of Ventura, California.
Pizzadude: Fun Free Fonts from a talented designer in Denmark.
Larabie Fonts: King of the free font, Canadian Ray Larabie's fonts are awesome.
Nick's Fonts: Better grab these fast!! Nick's planning to take them down soon. He's recreated classic period fonts from the '20s and 30's and has done a fantastic job. You can preview the fonts and download them from this page as zipped TTF files. (Mac users, you'll need a TTF converter to use them, though. Get a converter here.)
However, if you go to this page, you can grab Nick's Free Fonts in either Mac or PC formats without Mac users having to convert them from TTF files. These are classy, amazing and FREE fonts. Grab them all, before they're gone!! The design and kerning of Nick's fonts are perfect.
That ought to keep you busy for a while....