Grab the first one that looks interesting to you and read it.
This question probably looks a little more sensible, from the outside, than it is to me. Indeed, chances are if you read The Discworld books yourself, the question makes some sense. Right? You can tell, thinking about it, that there is a disjointed, strange order to the way the stories introduce characters and those characters then develop over time.
There’s a perspective on Terry Pratchett’s Discworld books that says those books have ‘ideal’ reading orders. If you’re not familiar with Discworld, it’s a satirical narrative universe that Terry Pratchett wrote in, starting with The Colour of Magic in 1983 and concluding with The Shepherd’s Crown in 2015, published posthumously. Thirty two years of non-stop fiction in one single narrative universe, why, that’s got to be a big and complicated story, right? How do you approach a thing like that? So many books, do you just start at the first one?
The content creator then slaps the hand and says wait, no! No, you can’t start with the first one, you see, because that one isn’t like the others, at least, not until… book… let’s say… seven. Or maybe four. Possibly five. Look, the important thing is to make sure you have a list, and maybe show a diagram, and talk about how, no matter what, don’t start with the first novel.
I used to agree with this position but it was in a time in my life before I could announce any silly opinion and get paid for it. Unlike now, I think. Point is, that if you go looking for ‘Discworld Reading Order,’ it seems it’s a very widely covered topic, which, thankfully, with so many people addressing it, means there should be a simple decided answer.
There isn’t, of course.
I think this question though, demonstrates a kind of complete failure of appreciating the Discworld books as they are. It’s the kind of mindset that thinks of Discworld as a series of books, rather than a set. It’s a vision of these books that treats them as, well, as units of a greater continuity, rather than stories contained in and of themselves.
It’s a conversation that frustrates me for a number of reasons, but two I’ll mention here. The first is it kind of assumes that readers are idiots? Like that readers aren’t capable of starting reading a book and going: Oh, I don’t really care for this but maybe I’ll try something else. It’s this kind of nerd proseltysing, where the idea is that someone might look at this exceptional book series of universally praised books and decide that if they dislike the first book they tried, that’s it, there’s no reason to bother looking at any others. And even then, if they did and they do, then that’s okay. Discworld is a great series of books, it might be literally the best books their genres, but that doesn’t mean that anyone is somehow incomplete or lesser for trying them and deciding not to read more.
The second thing is that it wastes one of the coolest thing about the Discworld books. That is, every book is a single, coherent, explicitly explained story. Barring for one book, none of them need any of the other books to get a beginning, middle, and end. The characters are not holding their breath for development that never comes; they are each individually developed in the stories that need to use them and put them in focus.
Discworld is not a series you need to read all of to make sense of some greater whole. It’s one of the strongest thing about Discworld books. They really are as simple as ‘if this one looks interesting to you, read it, and if it doesn’t, don’t worry about it.’ Because eventually, if you get the bug for Discworld, any given book that inspires your interest is going to have in it infrastructure for exploring other things. You can just pick up a book, read it, and go for a walk.
I think people underestimate Discworld. They also underestimate readers. These books are engaging and funny and interesting and none of them are dealing with concepts so obtuse and unexplained that you need a ‘proper’ grounding anywhere.
And thus, we come to my advice: Pick up whatever book looks interesting and see if you like it.
The rest will take care of itself, and you will have a wonderful journey ahead of you.