What inspired this question for me was reading Alex Haley’s “Roots” after having just read “Beloved” by Toni Morrison. I thought that the two taken together give a wonderfully detailed image of American slavery and it’s effects on the body (Roots) as well as on the soul (Beloved).
Another that came to mind was Jack Kerouac’s “On The Road” and Hunter S Thompson’s “Fear and Loathing in Las Vegas” as I personally felt that FaL was written as a direct parody and skewering of the kind of transcendentalist optimism we see in someone like Kerouac.
I guess I’m thinking of books that look at similar issues from complimentary angles or books that seem heavily inspired by others and almost responding or expounding, so that you come away having learned more than the sum of their parts.
EDIT: Doesn’t have to be all fiction. Non-fiction is welcome as well.
I’ll go for a trio: Moby Dick, The Grapes of Wrath, and Invisible Man, in that order.
It’s hard for me to quite articulate why, but they all felt similar to me, in spite of being completely different. I guess they’re three definitive “great American novels” that each explores a dark side to the collective American psyche and Western, capitalist culture in general. Plus, they’re all fantastic reads.