Pratchett’s got oodles of American fans, so I’m not sure the “culturally specific” explanation accounts for it. I “got” a lot of the things from your link when I was reading–I was fond of ballads, particularly ones about fairies, so those references were not lost on me. I think it’s less that I’m missing a majority of the jokes, and more that Pratchett isn’t my particular sense of humor. There’s something rather self-conscious about it, and instead of thinking about how naturally funny it all is, I notice that Pratchett’s being funny. But like I said, I’ve only read one or two of his books, and I may like future ones better.

I’m actually surprised that Americans can understand Pratchett at all, because so much of the humour is culturally-specific. I’m a Brit now living in Canada. I would dispute that his humour relies on irony – it’s part of it, but for me it’s more to do with the rich cultural and literary references which allow the works to be read on so many levels. The more levels you understand, the more you ‘get’ the humour.

The mainstream Discworld novels are many-layered – they can be enjoyed on a surface level by young adults, but I well recall that when I read a book report my son did in Jr High on a Pratchett book, he’d entirely missed the more subtle levels such as in-jokes referring to Chekhov’s plays, political allegory and cultural references that just went over the head of someone who’d spent most of his life in North America (and I suspect go entirely unrecognized by many devoted Pratchett readers on both sides of the Atlantic). But that’s OK – he still enjoyed the books reading on the level he could comprehend – but in a few years he may find himself enjoying the books on a totally different level.

In terms of the Tiffany Aching books, they’re aimed at Young Adults so you’ll find fewer literary allusions – but the cultural and linguistic references are very deeply layered. For me, half the pleasure in these books is the little jolt of recognition when I encounter something based on folklore, linguistics, history or whatever. You might have fun looking at some of the notes on the Wee Free Men on the L-space Web (a Pratchett fan site) where folks have amused themselves by providing illuminating ‘footnotes’ to some of the references. http://www.lspace.org/books/apf/the-wee-free-men.html
I’d be interested to know how much of that stuff you ‘got’ at the time you were reading the book.

Of course, you may well read it and then think ‘So what? I still don’t find that interesting/funny’ but it might give you a better idea of what other people find funny/intriguing in his work. Sense of humour is a deeply personal thing, and sometimes things which are so deeply culturally specific just don’t ‘translate’ well.

Then, if you WANT to give more Discworld books a try, go with the later ones rather than the early ones– the early ones are more outright spoofy (and the first couple among the most uneven books in my opinion). Night Watch is a favorite of mine. As for the rest of the Tiffany books, I personally DIDN’T like Hat Full of Sky as much as Wee Free Men, but Wintersmith I loved almost as much.

I hope so too! I may try some more Terry Pratchett, though, because I want to give him a fair chance.

Indeed? Well, there goes my theory. Obviously lumping humorists in together when they don’t belong together then. :/

I heard that song so much. It played all first semester my Freshman year of college. Ouch. Pain. Please knock me out with a mallet to end the associated flashbacks.

The secret initiates-only irony is the lack of irony in a song called “Ironic.”

Have you seen the drunk cooking one yet? I can’t remember which DVD it was on…

Do you have a favorite of his standalones? I’m willing to read at least three of his books before giving up, so supposing A Hat Full of Sky disappoints me, what would you recommend?