I read this one because I've read a few other Pynchon books that I liked. Gravity's Rainbow is similarly muddy but he got me with the v2 rocket thing (rockets falling randomly over London but also always some place the main character was a few days ago, but also statisticians say it's just a coincidence) caught my imagination.

Which leads to your larger point: if the world started with something like Finnegan's Wake I doubt we ever would have heard of Joyce. But Ulysses was something new and maybe even a good read. So these artists build trust by producing things we do think are good and then they step out into unknown territory and try something unexpected.

There are no guarantees that it works out. And they definitely get to draft off their previous success. But sometimes it works out and we end up adapting our sensibilities to this new thing and it turns out to be quite enjoyable.

(I don't think it worked out for Pynchon here--it will be a while before I read another one of his books)