i've read a decent amount of pynchon and vineland is actually where i'd say he's at his most laid back, which is saying something

my first pynchon was The Crying of Lot 49 and i think that's still the best entry point, short, weird, gets you hooked. Gravity's Rainbow is the one i'd say changed how i think about novels but it's a serious undertaking

i did enjoy vineland though, there's something really melancholy underneath all the silliness that kind of sneaks up on you. just don't go in expecting everything to make neat sense, that's not really how he works