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I like to read, but I tend to be picky, so I'd like to hear what you all have to say about the Discworld series. I find it popping up on TvTropes quite a lot, but there are 41 books in the main series, and I'm not sure if I'm supposed to read them by publication date or not, so I don't know if I should try or not.
Is it anything like Diana Wynne Jones Derkholm or Howl's Moving Castle series? Or anything at all like Homestuck or the Hitchhiker's series or the Harry Potter series? (Yes, I know, I should be ashamed at how pedestrian my reading habits are, but at least I'm trying to expand.)

I believe there was a flowchart made for the Discworld series. I am not sure how accurate it is, though.

Discworld is very much an absurdist book series. I would place it similar to The Hitchhiker's Guide to the Galaxy books, or even a little Xanth.

If you would like to test some of Sir Terry Pratchett's writing, I would suggest Good Omens. It was cooperatively written by him and Neil Gaiman, and stands alone. Getting started will not require you to read any other books.