Hmmmm... I don't know what to make of that. Can you give an example of the contemporary philosopher examining what his/her epoch reveals to a thinker of another generation?
Žižek is one example, of course; his implementation of Hegel and Lacan has really created a new brand of psychoanalytic cultural theory for the 21st century. Lacan was a profound reader of Hegel, and entirely disagreed with him; Žižek, on the other hand, argues that Hegel's thought is actually compatible with Lacan's, but neither theorist was quite able to "think" such a reconciliation.
Another example would be Fredric Jameson as a re-reader of Marx, someone who has tried to discern what Marx would have thought of 21st-century globalism (as he does in his book
Postmodernism and his collection of essays,
Valences of the Dialectic). Another example might be Judith Butler, whose knowledge of Foucault and Derrida has shown how both might have been influential in the field of gender studies. Finally, someone like Quentin Meillassoux, whose work takes up Hume's problem of induction/causality and explores its consequences in the wake of vast technological proliferation and scientific expansion.
I'm also somewhat surprised by your accusation that Nietzsche didn't understand Hegel, since what I've heard is that his ability to utterly denounce Hegel resulted from very rigorous studies of the latter's material. Robert Pippin, one of the premier scholars on Hegel today (and there aren't many), respects Nietzsche as a reader of Hegel.
I'm also trying to read material that I think would influence my characters and I've noticed that a lot of strong-minded girls in their late teens/ early 20s really love Rand's novels.
Rand is an individualist, so it would make sense they would find her appealing, particularly as a female individualist writer.
Although odd, since Rand also composed highly misogynist prose when you really break it down. Rand was obsessed with what she imagined as the "ideal man," a figure that manifests as Howard Roark and Hank Rearden: "What I
was ready to write about was a woman's feelings feeling for her ideal man, and this is what I did in the person of Karen Andre [from Rand's play
The Night of January 16th]". However, this figure (which Rand, of course, believed to possess specific "objective" qualities) is nothing more than a highly misogynistic portrayal that results from a warped feminine fantasy. Just take Karen Andre's lines from the play:
KAREN: He seemed to take a delight in giving me orders. He acted as if he were cracking a whip over an animal he wanted to break. And I was afraid.
STEVENS: Because you didn't like that?
KAREN: Because I liked it...