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Are you talking about Gravity's Rainbow? Yeah, that is a hard book.

His first novel (V.) is similar in prose though and was so enjoyable for me at a young age I have been planning to read it again.

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Gravity's Rainbow is not worth the slog, IMHO, unless you like beautiful plot constructions and vulgar wordplay. As a commentary on literature, as a novel, as a piece of writing, and most of all as a story, Mason & Dixon is (by far) Pynchon's greatest work.

The Crying of Lot 49 is the foil—short, with a meaningless story only good for the experience reading it.

I'd say meaninglessness is a theme of the story, which is different from the story itself being meaningless.

I don't think Lot 49 is meaningless at all -- it has a lot to say about people who get wrapped up in conspiracy theories and how once you go down that road, everything begins to look like part of it. That's as relevant to politics today as it was in the 1960s when Pynchon wrote it.

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