Thomas Pynchon is one of those names in the literary world that carries a whole lot of weight. Whether readers like that weight is of course up to each person's reading preferences, but his name is weighty nonetheless. If you know his name at all but haven't read any of his books, you're probably aware of Gravity's Rainbow due to its reputation for being both profoundly convoluted/difficult for many, but profoundly exceptional for many others (while perhaps still being convoluted/difficult even for those who enjoy it).
If you're the kind of person who sees that hefty reputation and raises your eyebrow with intrigue, but are hesitant to pull the trigger for any reason, I would highly suggest reading Inherent Vice as your first Thomas Pynchon novel. Many longtime fans of the author will tell you that The Crying of Lot 49 or Vineland are the best places to start, and in terms of stylistic preparation for Gravity's Rainbow those might still be the right places to start.
But if you've never read Pynchon (or really any author) before, I firmly believe in starting off with something that you're most likely to enjoy rather than starting off with something that will give you the best preparation for others in their oeuvre for potential difficulty or stylistic reasons.
Inherent Vice is a hilarious psychedelic noir story that does a phenomenal job of instilling the sensations of 60s/70s hippie counterculture around Los Angeles. A weed-fueled fever dream that is unapologetically genuine and undeniably southern Californian. It gives hints towards Pynchon's verbose and meticulous style while remaining lighthearted and engaging. It does still require a certain amount of attention to keep track of some of the longer sentences and fairly high character count, but with Inherent Vice it feels less like an absurdly intelligent author flexing his writing skills and far more like a stoner's meandering stream of consciousness.
In my opinion, subjective of course, I'm inclined to say that if you've never read Pynchon before, try Inherent Vice. Because I think if you don't like it, you're not that likely to enjoy anything else in his body of works. Comparatively, I think it's not unreasonable to say that if you've tried something else of his, say Lot 49 or even Gravity's Rainbow, and didn't vibe with it, you could 100% still pick up and enjoy Inherent Vice.
by PsyferRL