I always kind of wish HHGttG was as good as the geekdom's fondness of it suggests. I read it, I enjoyed it, but really, it is such a depressing series. And there is very little that's particularly funny or interesting after the first book and a half. So many dull and drawn out scenes of characters in miserable situations. And that whole tortured Krikkit gag trying to explain the origins of cricket. Sigh.
I completely agree, it's one of those works where the pop culture lens filters a lot of things. I think Adam Douglas himself mentions in an interview that the later HHGttG books reflect his personal depression, and the enormous time pressure they were written in. Probably the whole series should have been one book, but it also makes it feel a bit human - here's this really smart guy with a lot of brilliant ideas, he just didn't manage to fully finish everything before it's shipped.