xkcd - A webcomic of romance, sarcasm, math, and language - COMPLY.
Apple II madness! | MetaFilter. Apple II versions of Oregon Trail, Ultima IV, Where in the World is Carmen Sandiego? and lots more. Playable online, IE only though.
Dark Cut. Fun & funny medieval surgery game (I'm guessing it's probably a take off of Trauma Center on the DS)
Visit the archive if you wish to skip merrily through time in a devil may care fashion.