Having orignally read the books in order (more or less) and having read all of the non juviniles, I would like to point out that Prattchett builds his world a little bit more with each book.
It is probably correct that it is not essential to read them in order, but if one does not, there are nuances and references that you will miss if you only read certain ones.
The Librarian's name, for instance.
Many characters, Death for example, are introduced in the very first book and Pratchett only expands characters. He does not rehash them.
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