I find there tends to be two general categories of books; those that are exciting and interesting, so much that I want to recommend them immediately, and “slogs” that are just slow and unappealing regardless of the content. Some I get the jist of fast and a lot seems irrelevant like What is to Be Done, some like Fresh Banana Leaves the writing is just dislikable and repetitive. This is in sharp contrast to books like Half Earth Socialism or State and Revolution where I may be familiar with some of the content, but I really like the style and new information and want to recommend to people.
Do you agree with this categorization? Are there any books that you feel strongly about either way? I’m sure I’ve heard a lot of your recommendations before, but I want to know what will actually be fun to read, because some aren’t even if the content is good. I want to know which to prioritize reading.
The trick with Discworld is that the author got much better, and much more into actually-pretty-good-takes social commentary, as the series went along. The first few books ("The Colour of Magic" and "The Light Fantastic") are really funny but not really representative of his work as a whole. It's best to think of them as a sort of alternative-universe thing. I'd actually not bother with them until you read a good chunk of the rest of the series.
Every Discworld fan has their own recommended reading order, but I think a good starting point are these books:
"Wyrd Sisters". This introduces the series' witches, who are awesome and not exactly what you might think when you hear "witch". Their thing is that they try to avoid doing magic by instead doing psychology (what they call "headology"), because the latter is more effective in the long run. If someone is magic'd into doing something, they might stop doing it when the magic stops. But someone who thinks that something was their own idea might keep doing it. Imagine a mix of Hamlet and Macbeth, directed by Charlie Chaplin, and written by Rob Grant and Doug Naylor.
"Guards! Guards!". This introduces the City Watch, the police of the biggest city on the disc. Of course all cops are bastards. Which all the cops on the Watch would agree with. The Watch are down to three members, led by an alcoholic named Sam Vimes - and then they get a super-keen recruit from abroad who's the most stereotypically super-earnest-and-super-buff farmboy you can imagine and who has no idea what trouble he's gotten himself into. They drunkenly stumble into a plot by influential people who want to fill the long-vacant position of King through deeply-stupid-in-retrospect means. It's a D&D campaign written like a hard-boiled detective story.
"Soul Music". This is one of the Death novels. Death is a major character in the series. But he's actually a very personable type. He doesn't really kill anyone, he's just around when it happens, to help the soul involved move on. This is not the first Death novel, but it's the one I feel is the best introduction to him. More importantly it introduces his granddaughter-by-adoption, Susan. She doesn't technically have Death's real DNA, but she's got a kind of DNA-of-the-soul, so she has his abilities and has to fill in for Death while he's... going through some things. A musician is supposed to die in a barroom brawl, but he doesn't because his soul is being sustained by the music. Susan's job is to make sure he moves on to what comes next. Susan doesn't really want to because she, and the rest of the city, are utterly enthralled by the spirit of rock-and-roll that he's brought to the world. Shenanigans ensue. It's Blues Brothers a la Tolkien, and it is a ride.