It took me 4 tries to get through Catch-22.
The first three times, it was just a slog with no end. People kept talking about how "hilarious" it was, and I thought it was at best mildly humorous in a pained, old fashioned kind of way — yeah yeah trading eggs here trading eggs there, characters with gimmicks and catchphrases, etc.
The reason I gave it a fourth try was that, for the first time ever, I overheard someone describe the book not as "hilarious" or "riotously funny" (as described on the jacket and virtually everywhere), but as a grim, scathing, depressing look at America.
I was intrigued, so I read it one last time, completely ignoring the humor and reading it more in the vein of Ellison's "Invisible Man", or "The Great Gatsby". It was a completely different experience.
The book was grave, the vignettes were horrifying. The jokes weren't funny, they were seemed borne out of impotence and a desire to cope. It was almost as if the author realized that the darkness he was trying to get at, if played straight, would seem farcical or try-hard, so he instead resolved to offer it to us reflected and distorted through some lame jokes... and somehow everyone loved it just like that, completely at face value.
It would be cool if people gave it a shot without burdening themselves with expectations of "hilarity".
(Originally a reply to a reviewer I follow on GoodReads)