Suggestions for which Terry Pratchett books to start with?

I'm encouraging a friend toward the books of Terry Pratchett, and I'm at a bit of a loss as to which specific titles would be the best introductory places. I don't really want to start him with The Colour of Magic, as I disliked that particular book and I don't think it's a good idea to start my friend off on an author I love with a book I didn't enjoy. I'd be very happy suggesting a out-of-order novel, but the books I enjoyed the most -- Night Watch, Unseen Academicals, Nation -- I'm not sure would be the best places to start.

Does anyone have any suggestions?

This thread should be fun! I am looking where to start too. I have read Good Omens but that is all.

Nation actually may not be a bad place to start, if only because it isn't set on Discworld. Otherwise, what about Equal Rites or Guards! Guards!?

I read them in publication order, and while I agree that some of the earlier books aren't that great, I still enjoyed seeing the Discworld slowly develop. Mort and Guards! Guards! are good points to start, while still early in the series. The Truth is one of my favorites and also doesn't require previous knowledge of the world to enjoy it. Same goes for Going Postal.
Why do you think Nation wouldn't be a good book to start? It's a stand-alone and a great book as well! I agree about Night Watch and Unseen Academicals though, the former relies too much on already familiar characters and I just didn't really enjoy the latter.

There are such distinct groups in Discworld, that you can start out with any one of them. I like Guards, Guards or Men at Arms for the city watch group, Mort or Eric for Death, and although I'm not as big a fan of Rincewind or the witches, Equal Rites or The Light Fantastic are good starting places for them. Really though, you can start just about anywhere and decide if you want to go back and pick up earlier books with those characters.

I would say start with Wyrd Sisters and continue chronologically from there, then if they really get into him they can always go back and read the first few they missed.

I have had this discussion with other Pratchett fans and we all agreed whilst the first discworld books are not awful and have moments of brilliance in them he took a while to get into his stride, the characters are patchy and the plot is all over the place, it doesn't make a great first impression.

I agree with tottman, only with this caveat; decide what type of books your friend enjoys most, and begin at the beginning of that group. If they love mysteries, then Guards! Guards! is the place to begin. If they love books about empowering women, then begin with the first Witches book. If they like gaming, or wizardry, then go with The Color of Magic. I'm not sure how to categorize the Death books, except that they are wonderful. A comical take on industry? Go with Moving Pictures or Going Postal.

Here is my favorite chart of Discworld reading which gives the beginning for each series:
http://boingboing.net/2007/09/30/pratchetts-discworld.html

Agree with MrsLee.

I would probably start with the 'Industrial' series, because the pointed commentry is more obvious, unless youre firend is already well versed in fantay tropes.

I got a couple of literature-loving friends started by giving them Wyrd sisters - they enjoyed the parody of Macbeth. Another thumbs-up for MrsLee's advice!

I had hesitated over presenting Nation just because of the separation from Discworld. Not that separation is exactly bad, just that I worried following up from such separation might be jarring -- sort of, 'Now here you go, start on a 40-odd series that has nothing in common with the book you just read.'

But maybe that won't be a problem, particularly if I give him Good Omens as well. With the Discword Going Postal. Those three novels could be a good start to things, yes? But maybe four, with Small Gods? My problem is I keep getting side-tracked, thinking, 'Oh, but Thud! was also so good, and I loved Feet of Clay, ohhh and also Monstrous Regiment' but those are possibly better as a secondary or tertiary novels.

Maybe if he reads fast enough, I can present him with Hogfather come December.

The tricky thing about the Discworld series, is you really have to read several books from the various types to know whether it is for you, that is unless like me, you know it right away. See, I could barely finish Small Gods or Monstrous Regiment, but there they are, your favorites. I lucked out, the first one I read was Hogfather, and it suited me perfectly, with it's spotlight on the various lovely holiday traditions and what their actual origins were. I gobble that stuff up.

ETA: In fact, perhaps that is the Death series theme? Looking at traditions and assumptions we take for granted and turning them on their head?

I'd suggest Guards! Guards!, Going Postal, or The Truth. However, I think it is best if you know of something he is interested in and give him a Discworld book with that theme. That's how I started my father on Discworld - he loves sixties rock music, so I gave him Soul Music.

I started with the color of magic and was hooked from there