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I fall somewhere in between JSWolf's always adamant insistence on reading in published order and the read whatever takes your fancy. I think Jon's right to a certain extent, in some books you do sometimes briefly meet characters in passing that you would know better if you had read the books in order, in which case the full impact of the scene may not be achieved. But, unlike Jon, I don't think this is crucial to the enjoyment of the books.
Yes, the first books, The Colour of Money and The Light Fantastic, are the weakest of the Discworld series, but they are in some respects also the simplest and most easily accessible to younger readers (at least until you hit the books written specifically for younger readers), so as starting points for kids getting involved I think you could do worse. (And, as a bonus, you get most of the key details you need to know where you are, whatever book you pick up next.)
(And what follows gives no hint of their publication order, just the order they came to mind...)
If you're not insistent on Discworld, I also thoroughly recommend Pratchett's books written for younger readers, they're great fun whatever your age. The Johnny books: Only You Can Save Mankind, Johnny and the Dead, Johnny and the Bomb are all good fun and short easy reads. And "The Nome Trilogy", sometimes sold as an omnibus these days as The Bromeliad, but originally: Truckers, Diggers and Wings. I love that little series, like a miniature epic and great fun. Nation is very good but much more serious in nature. I enjoy The Carpet People too, but it's not among his best.
I really like Good Omens but probably not the best starting place for getting to know Pratchett. Strata is an interesting read - an early SciFi version of the Discworld. Dodger I found less enjoyable than most, but I've only been through it once and I will probably revisit to see if it was just a mood thing.
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