If the Gumshoe Fits: the Thomas Pynchon Experience

There are basically two sorts of Pynchon novels[1]:

Gravity’s Rainbow, V and Against the Day are these monumental books which are sometimes really harrowing and hard to read (amazing in my opinion, but tough to read none the less).

Lot 49, Inherent Vice, Vineland and the new one are kind of “weird noir” gumshoe novels - funny and full of whacky conspiracies etc.

Bleeding edge is more like the second lot. I would definitely recommend people to read The Crying of Lot 49 and/or Inherent Vice to make up their minds whether they like Pynchon. Then you’ll know whether you want to invest in reading V or Gravity’s Rainbow etc.

[1] I’m gonna leave Mason & Dixon to one side because it’s sort of its own thing.

Bleeding Edge is another one HNers would probably enjoy.

With Gravity's Rainbow you can either read it and make peace with the fact that every acronym, reference, character, plot point etc. won't be fully understood or remembered (that's kind of the point with this type of writing style, imo), or you can read it with a companion guide kinda like how some people play video games.

I also liked Crying of Lot 49. Inherent Vice is also a bit of an easier time.