Where to start?

The great thing about this series is that you really dont have to read any book first; I dont think this can be emphasized enough. Knowing more about any specific character than is contained in one specific book is purely supplementary and not needed to fully understand what is going on.

^ This.

But what I then love is that if you DO know all the extra information, then there's lots of little easter eggs for you to enjoy. Names of places, events and passing remarks that reference other books and characters. Irrelevant for the main plot, but just a nice nod to those who've read more.

I read Thief of Time (26th book) first and was able to thoroughly enjoy it (still my personal favorite of what ive read).

Coincidentally enough that was my first Pratchett. I still love it.

My favourite 'series' would probably be The Wee Free Men though. Nothing has had me side stitching in laughter than the books featuring them.
 
I wanna jump in here and ask for recommendations too. Only read going postal and making money so far and loved it. I know they are a slight departure from the overall theme but i would love some suggestions.
 
Of all the Pratchett Disc World books I really like the Night Watch Sub-series starting with "Guards!, Guards!".
It's interesting how the Watch slowly develops bit by bit into a modern police force.
Using a Zombie for a plain clothes detective, an Igor for a forensic scientist, I love there version of a speed camera.
Commander (later) Lord Vimes is a really strong character, well supported by the likes of Captain Carrot and his Werewolf girlfriend.
There are four other sub-series, Wizards "Colour Of Magic", Witches "Equal Rites", Death "Mort" & Moist von Lipwig "Going Postal".
As well as some very good stand alone books such as "Pyramids", "Small Gods" & "The Truth".
I also recommend his non-Disc world books "Dark Side Of The Sun", "Strata" & "Nation".
All Good Stuff !!!
 

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