All the Apple juju in the world can't help you if you're selling crappy content. Jaffe, Rubel and many others have covered the whole "$1.99 for ads" thing on iTunes pretty well, but what about the rest of the stuff Apple is selling there? Apple can count on my downloading the latest episode of "Lost" every week. It can also count on selling me a smattering of comedy routines on a one-off basis. That's about it.
I understand they need to prove the concept to a lot of skeptical folks, but offering first-season episodes of South Park and Jackass ain't gonna get the job done. Anyone who is a fan likely already has this stuff. The content is stale, and it shows. One needs only to look at the comments under South Park in iTunes to see how pissed off people are about it. (I'd link them but I can't.)