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I resisted Pratchett for years because I wasn't a fantasy fan, until I succumbed and picked up, I think, Pyramids, which is Pratchett's take on ancient Egypt, Greek philosophy (and ancient Greece), and of course English style boarding schools. One thing about Pratchett's work is that he is incredibly widely read, so many of the allusions and puns he uses may pass over the head of a teenager whose education is not so broad.
Guards, Guards! is his take on numerous things, including swashbuckling, cops, dragon lore, cultists and probability theory...
Which one to start with? Pyramids, possibly, since Egypt and ancient Greece are moderately familiar to everyone. Well, sort of. I read them well out of order, at first, because there were quite a few published and I was catching up. No worse for the experience.
Then there's Wyrd Sisters, which is Macbeth revisited. It is complicated.
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