Being known for being a stone-cold Terry Pratchett fan – particularly of the Discworld series – I’ve been asked for recommendations about where someone should start if somebody was interested in the series. The answer is… it depends.
Essentially, the Discworld has gone through at least 3 upgrades since it was created. Version 1.0 was pretty much a straightforward comic treatment of the sword-and-sorcery genre, complete with various good-natured parodies of other fantasy series. Somewhere around Small Gods (in my personal opinion) we got version 2.0, which is where Pratchett started contemplating the Discworld as a place where serious (yet comical) stories could be told (as opposed to straightforwardly comic ones). At some point – probably around the time that the Science of Discworld series came out – we got version 3.0, which is where we start seeing a fully-conscious examining of the implications of Discworld.
None of these iterations are necessarily superior to any other; but it does mean that new readers may be confused by the sometimes wide divergence in styles between any two books. I therefore suggest that you go by the sub-series, which I’ll discuss below. I’m not going to list every book in said sub-series: there are a lot of Discworld books, and they sometimes cross over into each other’s narrative thread.
Rincewind (The Color of Magic, The Light Fantastic, Interesting Times). This character was the hero of Pratchett’s first Discworld books; his entertainment value comes from his incompetence in magic, his unapologetic cowardice, and his inability to let either get in the way of avoid saving the day or the Discworld on several different occasions. Three other characters from this series would be TwoFlower, the Discworld’s first tourist; Cohen the Barbarian, a barbarian hero who has been legendary for decades and decades and decades; and the Luggage, which is… the Luggage. It’s a good place to start if you like a good-natured ribbing of heroic fantasy series.
Granny Weatherwax (Equal Rites, Wyrd Sisters, Lords and Ladies). This is a series of books about rural witches, and how they’d actually operate in a world full of magic. Granny is one of those characters that you may not always like, but enjoy reading: she is highly skilled in her craft, and would probably quite enjoy being a bad witch if it weren’t for the unfortunate fact that she has too strong a sense of right and wrong. This is not a series about sentimental witchery: even the crystal-and-magic-candle parody witch (Magrat) drops the fluffy bunny act when pressed. This is a series (most obvious in Lords and Ladies, which is really about real elves) where the blood-and-bone aspects of rural magical traditions are obvious. It’s also funny, mostly because it has Nanny Ogg in it (imagine a Benny-Hill ribaldly-style grandmother with powerful magic: good, you’ve got Nanny). This series is good for literary references and people who like to know that their authors have at least read up on their folklore.
Sam Vimes (Guards! Guards!, Jingo, Night Watch, Thud!). Terry Pratchett’s police procedural series, and Sam Vimes is probably the character of the series who has shown the most development as he went along. Vimes started off as the alcoholic, defeated head of a Night Watch in Ankh-Morpork, a city where the Thieves’ and Assassins’ Guilds are officially recognized and legal; his ascension to what is possibly one of the most subtly terrifying (yet endearing) characters in the Discworld universe tracks the reintegration of the Watch back into Ankh-Morpork’s way of doing things. The books in this series have become more and more like non-fantasy detective novels: two important secondary characters are Captain Carrot, who is secretly True King of Ankh-Morpork, and Patrician Vetinari, who is the despotic ruler of the city. It’s just that Carrot apparently thinks that the Patrician is doing a better job of ruling the place right now than he would, and Carrot is right: I’d vote for Vetinari myself. This series is fun for readers of detective/mystery fiction, as well as a good introduction to Pratchett’s other Ankh-Morpork stories.
DEATH (Mort, Reaper Man, Hogfather). DEATH is precisely that: the anthropomorphic representation of death. Skeleton, robe, scythe, the whole nine yards. He’s one of the two most likely characters to show up in any given novel*. He’s also possibly Pratchett’s most well-liked character, too – mostly because it’s fairly clear that, in a setting where the gods pretty much act like they do in our myths, DEATH is one of the few supernatural entities out there who is essentially on humanity’s side. Other characters revolving around him would be Susan Death, his granddaughter (it’s complicated), a sensible sort who finds being a quasi supernatural entity herself highly exasperating; and the DEATH of Rats, who is there primarily to be amusing. This sub-series gets a lot of the metaphysics, and most of the serious thinking about the nature of humanity and whatnot. Plus, end of the world scenarios, for some reason.
That should do for a start: there is a lot more out there, and I haven’t even gotten into the stuff for kids, or the entire technological development subgenre. I suggest for concordance purposes that people also get The Discworld Companion, and both GURPS Discworldand GURPS Discworld Also: they’ll help you fill in a lot of the blanks. All in all, it’s a fun series to dive into, so by all means, do so.
*The other being the Librarian, who is the librarian of Unseen University, which is the Discworld’s greatest magical university. The Librarian was turned into an orangutan in the beginning of the Discworld series, and has been adamant about not being turned back into a human ever since.