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 feel like Iris Murdoch’s Black Prince was written as a response of sorts to Nabokov’s Lolita. The flowery style in Black Prince reads nearly like a parody of HH, and the plot is weirdly similar. In both books you have the protagonist and his shadow nemesis, and the protagonist in both books are unsuccessful writers while the nemesis is successful and rich. And then there is the jilted middle aged woman who play largely the same role in both books, albeit with different endings.