[ATDrake]

I started reading them almost entirely out of order, due to being kind of limited to what the library had in stock at the time before I went and bought them all, and I don't think I particularly suffered from it.

But for a new reader who can afford it, I'd suggest finding one of the natural starting points for the various series-within-the-series, like the "Watch" or "Death" or "Witches" or "Wizards" books.

I think you can freely skip over the earliest and often weakest books and come back to them later if you've particular interest.

For example, Equal Rites is technically the first appearance of Granny Weatherwax, and it's an okay read, but Wyrd Sisters is by far more interesting and better-written, and really the best place to start reading the "Witches" (also very useful for best understanding of the relationship dynamics and Magrat's character development through Witches Abroad and Lords and Ladies, though I think I myself read those two in reverse order).

Similarly, Moving Pictures is probably the best "Wizards" book to start with, even though Sourcery comes earlier. Mort and Guards! Guards!, however, are very solid beginnings and the best starting points for the Death and Watch books, respectively, although you'd still be doing pretty well if your first Death book was Reaper Man instead (but it really does help to read Mort before Soul Music, though).

A good standalone starting point for the series is Small Gods which is basically not strongly tied-in to anything else and neither "required" prequel or sequel reading to any other book (although the History Monks and the Omnian religion do pop up strongly in later books). It's pretty indicative in tone of the later Discworld books as they get more "serious" as they go along.

Similarly, Pyramids is also pretty standalone for the same reason, and a good representation of the earlier, "lighter" tone.

Between the two of those, you can see which, if any, of the two overall styles of Discworld books is more appealing to you, and judge whether you want to start at the more comedic and spoof-y beginnings, or would rather read the more "mature" works first and go back and fill in the background setup later.

Also standalone, the relatively recent Monstrous Regiment, which is set away from anything else, but does reference Ankh-Morpork quite a bit. So it can be enjoyed without reading the other books, but you get an idea of who's who and what's what in the "modern" Discworld setting.

And also The Amazing Maurice and his Educated Rodents, which is completely standalone and a very good YA fantasy if you're not averse to trying out younger readers' books.