kgalias comments on Yet more "stupid" questions - Less Wrong
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I particularly enjoyed the City Watch series. It also seems to be the most "non-ridiculous" and down to earth, which can help at the start.
It actually took me a while to warm up to the Watch books; when I read Guards Guards, I was expecting more laugh-out-loud moments of the kind that there were in the sillier early books.
/me read Discworld in publication order