Which Terry Pratchett novels are the best starting point for readers new to the Discworld?

My advice (and I go back a looong way - I have TCOM in the 1st edition pb) is to choose any one of the character/subject 'sets', and read through each one in publication order.

  • Rincewind
  • Death
  • Lancre/Witches
  • Moist Von Lipwig
  • City Watch
  • Standalones
  • Tiffany Aching

You'll find various sites that will categorise the titles in this way.

The other thing I would say is that it is far more important to read and enjoy the books that it is to agonise over which order is best! ;)
I'd modify that slightly to recommend City Watch first couple at minimum before Moist - as he is set in the same city but later in the City Watch series.
Ditto maybe a witches one before the first Tiffany Aching.
If you only had to read one subject then I would choose the City Watch novels. These tell you much about Ankh Morpork but little about Discworld as a whole If you want to know about that, then I would suggest the Rincewind stories. Death and Witches are nice diversions, and then there are the novels that could easily stand alone.

Though in all honesty (and as I mentioned previously) , I really see no reason not to read them in publication order.

The only thing I would say is that there are certain stories which can be omitted, which (to me at least) aren't of the highest standard, and whose omission will not detract from your enjoyment or understanding of the Discworld series. Personally I'm not a fan of of some later stories such as Monstrous Regiment, The Thief of Time and Unseen Academicals. And I'm not all that keen on Going Postal or Making Money. I think I preferred Terry Pratchett when he stuck closer to fantasy themes than the real world. From a personal point of view, I think that he peaked with Night Watch.
I'm one who would recommend reading them in the published order, and suggest you don't skip the first Rincewind books. They have a charm and spirit to them that is highly readable. I have re-read these first few and found they stood up well. If anything I enjoyed them more the second time around. The best are those mentioned by others, such as Wyrd Sisters, Guards! Guards!, and Small Gods. But I think it would be a shame to skip many of the others, and there's a sort of cohesion and bits of cross-referencing, when you read them in order, that works well.
I always recommend that people start with Guards Guards as the City Watch novels are easily the most accsessible and dont really require any previous reading of other novels although my personal fav has to be Jingo.
If the reader is a little younger, then I would recommend the Tiffany Aching Series [The Wee Free Men 2003, A Hat Full of Sky 2004, Wintersmith 2006, I Shall Wear Midnight 2010 but not The Shepherd's Crown 2015] as a start point.
They are [for the first four books at least] a much lighter read without being at all juvenile. They are pretty much self contained as a series, even though they do bring in characters from outside. And you get the Nac Mac Feegles as well ;)
I warn against reading The Shepherd's Crown until you have read a lot of Pratchett. It was the last book he wrote and for me you can see him fade on the page. It feels incomplete. The story is there but the "Pratchett" is missing. It is painful to read as you see what he was hoping to create but never had the chance.

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