Bookslut will tell you "not," but you would be missing something special. Most generally, revel in the language, the fun, and the set pieces. Don’t look for deeper meanings, in my view there ain’t none, and for the better. My specific tips:
2. The Crying of Lot 49. Short, fun, and somewhat scrutable. It is a common introduction to Pynchon, although Pynchon himself dismisses its importance.
3. Gravity’s Rainbow: The masterpiece. It doesn’t matter if you don’t finish it, the story falls apart in any case. Even reading the first fifty pages yields a high return.
4. Vineland: This short novel came after a 17-year hiatus. It has its defenders, but I find it unreadable and unpleasant.
5. Mason & Dixon: I love the 18th century, so you might think I could get into this one. Pam Regis tells me it has to be read aloud.
6. Against the Day: The new 1200-page monstrosity. How to read it? Lean it against your sofa, and wait until your wife starts complaining about it, thereby prompting you to pick it up and get it out of the way…
The bottom line: Pynchon is about the highest-IQ author out there, a mixed blessing. Start with Gravity’s Rainbow, or V, and hope for the best.
#15 in a series of 50.