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.
David Copperfield and Demon Copperhead
Yep, half the fun is comparing the stories side by side. I was essentially doing parallel reads and it makes for a really neat experience. Really makes you feel like you’re traveling through time. David Copperfield feels more modern by it, and it makes you relate more strongly to a classic (which some people have trouble doing because we tend to perceive people in the past as stuffy and more serious than they were), and it makes Demon Copperfield shine and feel all the more devastating all the while. Reading them together highlights how hierarchies and social and economical inequality affects the poor and working class, especially the resulting exploitation of children.