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These are the websites that I visit often. If you have any recommendations, let me know!

At BoingBoing.net, you never know what you will find in this blog-style semi-news publication. Posts range from the Sony DRM rootkit to how to make a fruit helmet for your cat. With many contributors, it is a site to check several times a day.

Fark.com brings together a lot of weird, funny or silly news from across the world. There are pointers to articles about bungling burglers, poor celebrity behavior or just plain odd or gross stuff.
Of special note are the photoshop contests held at Fark.com. Competitors are given a graphic or theme to work with and the results are often hilarious and confounding. See for yourself - you might not be sorry! Many an internet image meme gets its start here. O RLY!

Kingdom of Loathing is one of the most creative and humorous online games that you can play in your web browser. Character classes include 'Seal Clubber' and 'Accordion Thief'. In game mechanics allow you to fight undead elbow macaroni, mix martinis, cook and eat ramen noodles, and adventures in places such as 'Digrassi Knoll' and the 'Orc Chasm'. As Fark.com might say, hilarity ensues.

If you haven't heard of the Onion, you don't know satire. Political or cultural, it's all good. Every week they post articles from their hard-copy publication. But wait, there's more! They also add a parody of the president's radio address so funny that the White House threatened to sue them for using the White House seal. (Not related to the Kingdom of Loathing 'Seal Clubber' mentioned above.)

Slashdot is a venerable news / discussion for geeks of all types. News focuses on latest open source projects, digital rights and internet culture.
In addition to the news, slashdot is know for its witty (obnoxious) and expert (troll) commentary. If you can stand to wade through the comments, you may learn something. Then again, you may not.