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As for what is best later on, that's a tricky one. There are four or so main series within the series as it were, following certain characters, as well as some completely stand alone ones. I love the City Watch books (Guards Guards, Men at Arms, Feet of Clay, Jingo, The Fifth Elephant, Night Watch, Thud andt he upcoming Snuff), though the ones with the witches aren't far behind, especially Carpe Jugulum. The Truth is one of the best stand alone ones.
they're the funniest and most enjoyable I find. Vimes is a total badass.
The Death books are good as well - Mort, Reaperman, The Hogfather (Mr TeaTime!)
But yeah, any of the City Watch that charliepanayi stated are definitely worth reading. The Fifth Elephant is my favourite Pratchett book.
then maybe go on to the Nightwatch.
his books aren't usually the best ones, though The Last Hero (where he plays a supporting role) is pretty fun.
especially considering they started the whole thing off. It also eases you into the style of writing/humour that Tezza settled into for the later books.
While the Rincewind books are fine, reading them will not make it obvious why Discworld books are so good. They're too early in his career, he still hadn't fully worked out the rough edges. If you like, they're the Pablo Honey of the Discworld world. Some good moments, but pales in comparison to the later stuff.
Like charliepanayi says, I would follow the City Watch books, or the Death books. I really like the Truth too, though that's just because I like newspapers.
The Truth is by miles the best of the standalone (including the two Moist von Lipwig books, which were one too many to be honest) ones he's done. It's nice he's tried something different at times, but I wasn't crazy about the likes of Monstrous Regiment (which wore a major plot point into the ground by the end) or Unseen Academicals (which suffered whenever the wizards weren't around)
would be a bit of a let down.
Because I read them in Eric Idle's voice. Thank you adventure games.
... there are so many of them that Moousee's argument doesn't really hold water - reading one of the best isn't a let down afterwards because you know that there are more brilliant ones. In fact the joy then becomes reading as many as you can to see which can compete and which are even better. They're great and will get you to return again to Discworld to unearth more of the lore behind the characters.
Then try the Witches books, because Granny Weatherwax is pretty fierce too. Personally Rincewind has never really done it for me - I've tried a number of times but I just find him plain annoying. The first Pratchett I read was The Fifth Elephant - a midseries City Watch book and absolutely brilliant. I've been hooked ever since.
... the third of the City Watch books, it's by no means the best of the series but is a very good read nonetheless, as the characters are more developed than the previous Watch books. This then sets you up comfortably for Jingo, The Fifth Elephant, Night Watch and probably my favourite Thud!
and I genuinely think that I have benefited from that. I'd agree that Rincewind's books aren't the best, and over time his character becomes a bit of a tired joke, but as I said before, still a great introduction to the Discworld. I have enjoyed seeing his style develop, and also the evolution of the many Discworld in-jokes. Personal opinion innit.
...and the reading in order to an extent (I tend to be like that with books and albums alike). But to get you into a series it's still nice to start with a bang, hence my suggestion of Feet Of Clay - early enough in the City Watch series to then be able to read the next four (which are the best imo) and see the characters develop but good enough to get you hooked. The first two books are good too but just not as great, and the OP does ask for the best, so I think my suggestion is a good compromise. Can't agree about Rincewind though - I've tried The Colour Of Magic and The Last Continent a few times each but just can't get into them.
Honestly, I think that you could really dip in anywhere and would enjoy it. I love these books, and I have similar arguments with friends about them. Its part of what makes it such a great world, the fact that the characters are so varied.
Just on a side note, when you were a kid did you read the Truckers/Diggers/Wings trilogy?
... the only kids book of his I've read is Wintersmith, which was great, but that was at some point in the last year.
This thread has got me very excited - I've got a long train journey to Newcastle tonight and have never read Carpe Jugulum. A visit to Waterstones at lunch is in order!
Like Pyramids, Moving Pictures and Small Gods.