Abandonia
Hundreds of old DOS games, many of which are available for download if they're not currently protected by the ESA.
Dinosaur Dracula
Dino Drac is a blog by the same guy who used to run X-Entertainment. It has the same type of geeky nostalgic content, but is 60% less likely to be mistaken for a porn site.
I-Mockery
Satire written about pop culture, B-movies, video games, old toys and oddities, with plenty of nostalgia heaped on top.
Retro Junk
This site has user created articles and videos coming out the wazoo. If you have any fond memories of days past and want to write about it for the world to see, try submitting your junk here.
Sega-16
If you still think that the Genesis is the best system ever, or that the 32X and Sega CD weren't totally useless add-ons, this is the site for you.
Humble Bundle
Name your price for bundles of indie games and specify how much you want to go to the developers, charity or the Humble folks themselves.
GOG
Good Old Games, a place that offers a growing catalogue of older games for really good prices. All titles are guaranteed to work on Windows XP and Vista and are 100% DRM-free.