Sorry meant to get back to you. I would say only jump into Pynchon if you're up for a serious challenge, but it is a rewarding one. A few of his books in particular are the most difficult, dense novels ever written. I thought I had read challenging literature before Pynchon, and I had, but not in the same way.

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That disclaimer aside, there are a couple places you could start. Some folks say Inherent Vice is a good entry point, and I don't totally disagree. It's a very unconventional detective story with a disorienting, complex plot, but a whole lot of heart and some beautiful prose. That said it is certainly his most accessible and maybe least dense. There is a wonderful film adaptation from a few years ago.

The Crying of Lot 49 is a short novella and his first published "long" work. It has many of the themes that would come to permeate his career and the prose will give you a good idea of what to expect from his more challenging stuff, while still being rather short.

Gravity's Rainbow is probably his most difficult, but is worth reading at least for the absolutely transcendent prose. I did not know english could be written in such an inventive, elastic way until this book. It is my favorite novel. It is not a book that is about a simple plot that is easy to follow and at the end it all makes perfect sense. It is at times opaque, bewildering, and esoteric, but in such an enchanting way.

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Wherever you start you will be in a good place. I would suggest not starting with Mason and Dixon, however. It is incredible but it's written in 18th century style that is wonderful and unique, but is really the only example of it in Pynchon's oeuvre. Vineland also is regarded as not as strong as his other works, so maybe not a great start. Anyways, hope this helps.

Any time I've forgotten to turn in something on time I get an email, but beyond that nothing happens. I try not to do this out of respect for the library and other patrons, but I've had stuff for months after it was due until I remembered to turn it back in. It feels slightly wrong honestly hahaha.

The Passenger yeah. And same, we're all collectively better off with that guy still writing. After Pynchon I think he's the greatest living American prose writer.

Yea I just picked up (one of) the new McCarthy novels and Horizon Forbidden West on ps4. All the better that my library has a no late fee policy, so I can really take my time.