I started — and finished — with The Crying of Lot 49. I really tried, getting through about two-thirds of the novel before deciding that (a) I got it, I saw what he was about and where he was going, and (b) it was mostly BS, with what little wasn't BS being obvious and trivial insights into American society.
Like Pink Floyd, I think Pynchon is technically excellent but only that. He has nothing to say about the great themes that hasn't been said countless times before, and better.
I've personally known only two people who touted Pynchon as a great writer, and both were people to whom it was very important to be seen as being smart, as deep thinkers. I can see how Pynchon appeals to people of that type. I've read as much as I could find about Pynchon on line, and from what I can tell he is himself a person "of that type," so he appeals to people like himself.
Like so many artists, he thinks that his technical skills make his little hang-ups, injuries and paranoias worth being preserved for the ages. I don't agree, but that's just me.
Though I can not guess as to Joyce’s motivation for writing Ulysses, the modernism he invents strikes me as an observation of the secularism replacing the traditional Christianity at the time. So if secularism is a form of non-sense then his portrayal was nonetheless accurate.
I tried to like Pynchon.
I like people who attempt things, try things, create thing ambitiously.
But, often it’s not that good.