It doesn't get any better than this: Homestarrunner!
Be sure to check Strongbad's email, by far the funniest bit on the site.
Also a WIRED interview and a Tastes Like Chicken interview with the
creators Mike and Matt Chapman.
And for the true fan: a homestarrunner themed wikipedia?!
The system is down!
[edit] now available: strongbad_email.exe dvd
it's region free, check out the other goodies.