Ok, where do I start?
What’s his funniest?
Is that different from his best? If so, what’s that?
Have you seen the thread What should be my next Discworld book? that’s going on simultaneously with this one?
I believe that I have read The Color of Magic, Guards! Guards!, and Reaper Man. Of those three, Guards! Guards! is the only one I have some memory of.
Really, I’d suggest reading Good Omens.
I actually started with Reaper Man, which works fine as a stand-alone. Small Gods is also a stand-alone and one of his funniest. Guards! Guards! introduces you to the Night Watch series and has some pretty funny moments. Wyrd Sisters introduces the Witches, who are some of my favorite characters.
His later books focus less on comedy and more on characters, but are still funny.
Small Gods was the first for me and still a favorite. It’s a good standalone as it occurs mostly in a separate setting than the other story lines.
Guards! Guards! is a great starting point. Really though I like the Watch books better than any other books, mainly because of the characters, especially Vimes.
These are his best.
Then there’s The Amazing Maurice and his Educated Rodents .
Those are both YA and ease you gently into the world of richly done characters and bad puns.
The problem is that The Colour of Magic (and The Light Fantastic) altho hilarious and the first books in the series, were written as parodies of Fantasy literature. Later (and it is much argued which*) the series *became *great fantasy Literature.
Read either and you dont have to worry about starting in the middle. If you like them (altho they are a tad juvenile) then start at the beginning.
*Witches Abroad is my vote, but…
Another vote for Good Omens. Although it’s a collaboration with Neil Gaiman, the style of the whole book is very Pratchett and it’s one of the top ten, possibly the absolute best, books I’ve read.
Very true and a great choice.
I would say they are all good, just don’t expect perfect consistency of characters with the very first books. Vimes in Guards! Guards! is very different than he is in Night Watch. Not due to character growth, but due to a change goals of the author.
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The books I use to hook students are Guards! Guards!, Wyrd Sisters and Good Omens.
Which books are the best or worst are highly idiosyncratic. What I like and what you like are quite different.
Also, don’t listen to friends. All friends recommendations on books to read are crap as far as I can tell.
Read some summaries of the books, see if anything interesting pops up. See my posts in the other thread.
And whatever you do, don’t ever read the Tiffany Aching books. They are young adult books and are awful.
I have been reading the Tiffany Aching and quite enjoying them.
My favorites are the Discworld novels that center on Death. This includes Mort, Reaper Man, Soul Music, and Hogfather.
Read them from the beginning in order. You might not love some of the early books, but read them anyway.
Don’t listen to this, it’s objectively wrong. 
Like I said in the other thread, I can only read book series in chronological order. As luck would have it, the first two Discworld books are the weakest. They start as a sort of Bored of the Rings for general SciFi tropes, but by book 3, Equal Rites, Pratchett was finding his voice, and in Book 4, Wyrd Sisters, the rocket boosters kick in.
Wyrd Sisters is a pretty good place to start, assuming you’re already familiar with the Scottish Play.
Do this, at least to start. Or…
…start with Reaper Man. A great book in itself. Terry’s best IMHO.
For someone just starting off on Pratchett, I would give one of three or four recommendations:
If you’re the type (like me) who prefers to read series in order, then start at the first one, The Color of Magic. It’s far from the best: It took him a handful of books to really hit his stride. So if you do start here, know that it does get better.
If you want to start with the best, then Small Gods is a good choice. Not only is it excellent, but it’s also disconnected enough from the other books (mostly taking place hundreds of years before then) that you won’t be missing out on many connections. The downside is that, because of that same lack of connections, it’s not as clear what to read second. It’s also not as humorous as some of them, but it really doesn’t suffer from that.
If you want to start with a few books that fit well with each other, and ease you into the connections to the other books, then the Tiffany Aching books are a good choice, starting with The Wee Free Men. If you do this, though, then you really should read the other Witches books before you get too far (certainly, before The Shepherd’s Crown, Pratchett’s last work, which will be much less meaningful if you haven’t already read all of the other Witches books).
And finally, if you want to start with something that’s completely unrelated to Discworld, and which happens to be uproaringly hilarious, then Good Omens is a good introduction to Pratchett’s style in general (and to Gaiman’s).
GMTA. That’s pretty much what I said over in the other thread. Other than the “start at the beginning” bit. 