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It seems like after 100-200 pages of Gravity's Rainbow one of two things can happen:

1. The reader can't figure out what the hell is going on anymore or who anybody is. They give up and stop reading.

2. The reader can't figure out what the hell is going on anymore or who anybody is. They stop trying to make sense of the book and just read the words.

"Sure this guy has a toilet stuck to his foot now, and can prevent bombs from landing on him by magic or something. That's great, oh I think somewhere in that sentence it became 20 years earlier in a different part of town and there are two entirely different characters I don't know talking about something else. That's neat."

I'm not convinced you can compare Ulysses to Gravity Rainbow and Infinite Jest. Ulysses is not a postmodern book. Apart from their length, there are few things bringing these books together.

Gravity Rainbow has Pynchon's inimitable prose, constant segue between language register and mingling between the trivial and the profound. Infinite Jest is rambling and convoluted but it is extremely funny from the get go. Both can be a joy to read even if you don't finish them.

Ulysses on the other hand asks more from its readers. You can pretty much ignore the references in Gravity's Rainbow and still get (or not get) the point. Meanwhile, Ulysses is full of oblique metaphors and layered references which make it impossible to understand without knowledge of the referenced material.

It depends heavily on the genre, at least for me. So-called genre fiction--mysteries, sci-fi, fantasy, that sort of thing--really doesn't hold up to rereading, since the whole draw is, by and large, the setting and the plot. I still remember the solution at the end of Murder on the Orient Express, and I still know how Liu Cixin's theory of galactic civilizations is going to play out in the Three Body Problem, so there's not really a draw to reread those books: the language is serviceable but not exciting (at least in the translated TBP), there's no real symbolism/inter-textuality to dig into on further readings, &c. However, I still find myself rereading favorites like Gravity's Rainbow and Moby Dick every few years: the jokes are still funny, the language is still beautiful, and it's still enjoyable to ponder the references and metaphors the authors are (possibly) building.

Your comparison to television is a pretty good one, honestly. I've never really rewatched an episode of a serial television series (other than trying to refresh my memory when picking up a new season), since there usually isn't any substance there beyond the plot and characters, but I'll happily rewatch movies if the directing, cinematography, and/or acting are compelling enough.