When you do start with Pynchon, don't jump right into Gravity's Rainbow. It is a killer book, but it is a hard read and long. I'd suggest Inherent Vice, though it isn't super Pynchon-esque. I have yet to read it, but The Crying of Lot 49 is also suppose to be a good intro. Mason & Dixon and V. seem to be much heavier, for major Pynchon likers. From there, I'd suggest Umberto Eco as a similar author.