I discovered McSweeney's Lists sometime in college and have loved them ever since. My personal favorites are Implausible Claims Made by Vanilla Ice in His 1990 No. 1 Hit "Ice Ice Baby." and Lesser-Known Movie Prequels.
Today R sent me two that are definitely in the running for new favorites:
Famous Opening Lines From Novels Updated for the Modern Age
Rubber Stamps I Wish I Had for Grading Freshman Composition Papers
My sister was nice enough to remind me about this one too: Lines from the Princess Bride that Double as Comments on Freshman Composition Papers