Find someone who is able to articulate what one is doing and then apply it to the other. It will offer a fruitful perspective for understanding why you're enjoying what you're enjoying in McSweeney's. Interestingly, one of the very few links out of the Internet Tendency led to the web site for the Museum of Jurassic Technology. Most of what appears on the web site is the stuff that is only interesting because it's in McSweeney's. A lot of it is silly, stupid silly, not that far removed from South Park.
Thousands seem to love it.
It's as if the web site is a hangout for people who love the print version, or people who would love the print version had they ever seen it. It's not too hard to do reasonably well. You start with a sort of officialese, then add a spot of bashfulness and a pinch of absurdity. Something like that. New as it is, it's hard to pin down.