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The City Watch
Best starting point. Start with Guards! Guards! - detective fiction meets fantasy. Sam Vimes is one of Pratchett's greatest characters.
Death
Start with Mort. The personification of Death as a sympathetic character exploring humanity.
The Witches
Start with Wyrd Sisters. Sharp, funny, and full of Shakespeare and fairy tale subversion. Equal Rites is earlier but tonally different.
Moist von Lipwig / The Industrial Revolution
Start with Going Postal. Con man rehabilitated by government bureaucracy. Accessible without prior Discworld knowledge.
Tiffany Aching
Young adult but beloved by all ages. Best read after the Witches for full appreciation of Granny Weatherwax.
Rincewind / The Wizards
Where it all started, but the early books are the weakest. Best appreciated after you already love the Discworld.