Newgrounds, for the games and movies, VGcats, Penny Arcade, Another Videogame Webcomic, akward Zombie, and Name Game, for the humor, Along with "What Do You Do?" because not only is a one panel webcomic, but it's also community driven, as the next panel, the next part of the story, and what the author draws is selected by the author from one of the comments on the previous panel.
Dueling Analogs, as not are there webcomics, and funny videos and images from a variety of artists, but they also have a great list of great games, that list introduced me to the NESBox, and the SNESBox.
This site, for obvious reasons.
Tv Tropes, for the informational and humor value.
Cracked for the funny articles, and videos, especially Cracked After hours, 4 friends depating, discussing the merits of, and taking apart a variety of pop culture objects, places, and figures.
Natalie Dee, a daily cynical, pessimistic one shot comic series. The Worst Things For Sale, the husband of the person who does Natalie Dee picks one item for sale on the internet, and tells you why it's the one of the worst things for sale(ever).
The Oatmeal, another one shot comcic/image/cards/quizzes/jokes/tools/news/things, owned, run and drawn by a guy who is going to build a Tesla museum on top of Tesla's old lab.
And finally, the one you've all been waiting for, the end of this MASSIVE wall of text, goldenmachinegun.com, for being an awesome forum, with funny stuff happening all the time, and hosting an awesome group of TF2, TTT, Minecraft, and Killing floor servers.(/shamelessplug)