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.
From Hell by Alan Moore
Hawksmoor by Peter Ackroyd
Lud Heat by Iain Sinclair
All 3 of these books feature psychogeography and the occult history of London, with special reference to architect Nicholas Hawksmoor and the 7 churches he built around London following the great fire. Reading all 3 at once is a trip, and the second is my favourite novel of all time.