Glad to hear you are enjoying. I read Bleeding Edge when it came out, but was underwhelmed. It is characteristically Pynchon, but did not enchant me in the same way as did Inherent Vice some years earlier.
Still, his best novels have got to be Gravity's Rainbow, Mason & Dixon, and Against the Day. Those are the monsters. But you get out what you put in.
I would call a past version of myself an avid reader and I used to love the challenge of the big books. Loved Delilo’s Underworld, Wallace’s Infinite Jest, Lucy Ellmann’s Ducks, Newburyport, etc, but Gravity’s Rainbow is sitting on my shelf with a bookmark at around the 100 page mark because of how much it was asking of me every time I opened it.
I don’t have the headspace currently to give it a fair shake, but I hope I do at some point in the future, it’s my white whale for now.
One of Yale’s open courses has a lecture that covers The Crying of Lot 49[1]. A good place to start for anyone reading Pynchon for the first time.
Gravity’s Rainbow is my personal favourite, but takes an enormous amount of work as a reader. His far-reaching and darkly conspiratorial view of the world is punctuated by hilarious moments of slapstick comedy, which can help keep you motivated through the more difficult sections.
By comparison I found Underworld and Infinite Jest to be much more straightforward. I haven’t read any Ellmann, so I'll have to check her out.
"The Crying of Lot 49" is the only Pynchon novel I was able to complete (bailed on "Gravity's Rainbow" and "V").
I think it was an easy enough introduction to Pynchon for this lightweight so I can certainly recommend it as well. Paranoia and conspiracy are on parade mixed in with perhaps an international secret society? But I don't want to give anything away....
Even from reading the one book, you will start to see references to Pynchon in other nooks of popular culture (W.A.S.T.E., Radiohead's fan club, comes to mind).
Same thing happened to me. Then I decided to start reading ahead every 5 pages, scanning for something that engaged me. I finally found it in the chapter "Un Perm' au Casino Hermann Goering". I read a while more, and determined it was good enough to go back 80 pages and keep slogging. Pynchon's bricks sometimes require that cheat.
There's a popular edition of Gravity's Rainbow ("Penguin Classics Deluxe Edition, white A4 rocket pointing down on the cover) that, for some pressings at least, is a pretty poor print. Missing lines, haphazard paragraph breaks, etc. Given the writing style, I'd recommend any other edition (Penguin 20th century is good, blue cover with rocket schematics) to make it less of a challenge to read.
Gravity’s Rainbow is an experience. I don’t think it’s written to be fully understood and I personally think it’s intentionally working on losing its reader. That’s the point. You just have to enjoy the ride and accept you won’t get everything, maybe most of it. You can always reread if you want to but you already get a lot just from immersing in its spirit.
Of all the books I've failed to read, Mason & Dixon is probably the most annoying. I made it to about the 80% point and then life intervened and I put it down 'temporarily'. That was a few years ago so could probably have another go. I liked the Neal Stephenson-like vibe.
I'd give it to those first two, and V. I liked Against the Day but there's this long middle-to-end section of filth and depravity that I could do without, and it's weirdly more coherent than the rest. The other books have bits of that, but move on before long.
Still, his best novels have got to be Gravity's Rainbow, Mason & Dixon, and Against the Day. Those are the monsters. But you get out what you put in.