Message Boards
Gaia Online - To fully explain Gaia, I would need much more paragraph, which I'm sure you don't want to read. While Gaia does have its bad points (the biggest one being that it's sometimes overrun by illiterates), it's a great site that has a discussion on just about anything you can think of. And the customizable avatars are just icing on the cake.
Free Falling - Simply put, a great forum for writers. Friendly and supportive.
Webcomics
Earthsong - A wonderful fantasy comic. It sometimes gets a little wordy, but it's worth it to get to the beautiful artwork.
Angel Moxie - A great humorous webcomic about a team of magical girls.
Girly - A hilarious and crude comic that makes only slightly more sense than its predecessor, Cutewendy, whose archives are also on this site.
Sinfest - Sinfest was one of the first webcomics I've ever read, and one of my favorites to this day. There's never a dull moment, and yet it still manages to be thought-provoking. Genius.
VG Cats - To fully understand the humor of VG Cats, one must first make sure that one has a completely open sense of humor, preferably accompanied by a below-average IQ. You don't need to be a fan of video games to think that this is funny. After all, I hate most video games, and yet I still read VG Cats. So, you should too.
Media
Foamy - What??? You've never heard of Foamy? Is there something wrong with you? GO!
Hidden Mickeys - Being a HUGE fan of Walt Disney World, I absolutely adore this site. It has lots of information and hidden secrets about Disney World, Disneyland, and other Disney stuff.
Superdickery - You don't have to be a fan of the Superman comics to enjoy this, but a good sense of humor is required. Basically, it focuses on strange images found in DC and Marvel comics.
The Internet Movie Database - I'm an IMDb nerd. It has lots of info on every movie, TV show, and videogame you can think of.