I think I'd recommend Wyrd Sisters, Guards Guards, Reaper Man or Moving Pictures.
Those aren't the first books by any means but as I mentioned elsewhere a while ago, TP's first 3 or 4 Discworld books I thought were more "feeling the way" into this new world he was creating. I started to read them first in order and wound up putting them aside for a few years and then happened to read one of the later books which knocked me almost out of my chair laughing. At least that was my experience.
My favorite characters are Gaspode the dog, Death, Granny and all of the Nac Mac Feegle.
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