First off, Pynchon is hard. Especially the novels that will probably still be read in the 22nd century. Like Gravity’s Rainbow, for instance. To read that and understand some of the references, you actually have to understand statistics (like randomness versus predictability) and the differential and integral calculus.
And yet, for all that, it’s quite funny and bizarre. And yet takes a serious look at man’s obsession with war and destruction.
That said, it you want to tackle Pynchon, try The Calling of Lot 49. It’s short and gives you an idea of Pynchon’s absurdist style. It’s set in 1960’s CA, and is populated with right-wing militias, a secret society that may, or may not, be bent on world domination,
Another starting point is Inherent Vice, a mash-up of hippie nostalgia (waaaaay before my time) and crime fiction ala Dan Brown. So you’ve got hippie silliness, drugs, goofy sex and a deep, scary conspriacy. That may, or may not, be happening.
Yup. Pynchon always pokes fun at Conspiracy Theorists.