I'm with KD in CA on this one. Tootsie is a great comedy and it deserves to be higher on this list.
/dev/null, I agree with you on South Park Bigger Longer and Uncut. It is a funny movie, that has one or two too many songs. Meanwhile the television show has a lot of great moments. The movie is not their best work, which is why I question it being on this list. You could be right though, it might be a nod to it's overall success, but that still does not justify it being listed here.