What books work well for you are tied to directly what cultures and narratives you're experienced in.

I read Lord of the Rings in elementary school so when I discovered Beowulf and Shakespeare I threw myself down that rabbit hole because it was something related to a culture I already was directly adjacent to so I latched onto it as familiar. And ended up pairing nicely with C.S. Lewis, go figure they knew each other.

Reading Once and Future King makes an insane amount of sense if you're already familiar with Sword in the Stone, Frankenstein makes more sense if you've seen Brook's Young Frankenstein. Dracula makes more sense if you've read Frankenstein. Alice in Wonderland and Shakespeare. Lord of the Flies and Heart of Darkness.

That's kind of thing. Strong writing doesn't come out of nowhere, it's built on other strong writing, and the culture of that time. Shakespeare's writing was based on other stories, and those stories based on other stories.

Canterbury Tales for example arguably is the story that Once and Future King critiqued, just as it itself is a critique of feudalism.

That's the thing, if you're not already familiar with the culture and the story the work is about, you're not going to get the devilishly good bits that make classics classics.

Paradise Lost and Dante's Inferno are pretty meh if you're not already familiar with Christianity and varying retellings of those stories.

To do the examples you're doing Ulysses is tied to Joyce, the Odyssey, the Iliad by association, and his personal cultural background in the UK. Strongly suggest reading both Tale of Two Cities and Dubliners first, because Tale of Two Cities does a strong job of setting up the power of class division in historical Europe, which people outside of Europe may not fully understand, and Dubliners is tied to Joyce's personal background, as well as a subtly Jewish familiarity which has its own history. That's a long story.

Atlas Shrugged is great if you're looking at similar political lit, 1984 pay attention to doublespeak, BNW, paying attention to mass complacency, Mein Kampf, 1920s Corporatism in the US, something about Botox and Butter. Industrialism in London. That's all a rich pool, but you have to start with the introductions before you get to the meat. You can even look at classical Greek philosophical arguments and contrast it with Atlas Shrugged, but again, if you don't have bread around your meat you don't have a sandwich.

The living thread that connects all these stories is the relation of history to storytelling, something I'm involved deeply in, and that link is what allows me to rotate between cultures. Godzilla makes a hell of a lot of sense when it's read in connection to the hush hush horror of the 50s atomic bomb, and the cold war looming around it.