Recommendations

Here's where I tell you what you should like, and why you're a bad person if you haven't liked it already.

Webcomics
A lesson is learned but the damage is irreversible
Copper
Dinosaur comics
Dresden Codak
Great
Minus
Nedroid
Octopus Pie
Penny Arcade
Perry Bible Fellowship
Romantically Apocalyptic
Saturday Morning Breakfast Cereal
Scary Go Round
Xkcd

Video Series
Extra Credits
Hey Ash
Red Letter Media
The Spoony Experiment
Yu Gi Oh Abridged
Zero Punctuation

Gaming sites
Rock Paper Shotgun (Can't recommend this one enough)
The Escapist

If you've anything to add, send me an email, and if I like it enough, I'll add it to the list. Go forth denizens of the internet, and fetch me your links!