I have just started listening to Discworld during the drive with my Mum as we visit her Mum on the weekends. She enjoyed Mort more than I thought she would (though we also did the first Master and Commander book which she also quite enjoyed, so I guess you never can tell with some people) and now we've started Going Postal which so far I think is probably more directly "funny", closer in tone to Guards Guards which was the only one I'd read.
I am also halfway through Old Gods on my own time. What I find interesting is how different in tone his books can feel. It is a bit of a sprawling question on what to read though, besides "all of it" which is often not so helpful.
One day I will trick her into listening to a Le Guin.
While you can read any of his books out of sequence, I strongly recommend following one of the paths here: https://upload.wikimedia.org/wikipedia/commons/1/12/Discworl...
While none of the novels are impossible to read without having read the previous ones, many of them build on the themes and the characters that came before, and some of the magic is lost without knowing what came before.
Following that guide for first reading is probably the biggest mistake I have made in my 42 years of being alive.
First time you read it should be in publishing order.
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