Philosophy and Fiction: Ideas Made Flesh (Philosophical Novels, Plays, Movies, Shows, etc) For me:
Notes From Underground by Dostoesvky. I was a clueless, impressionable college freshman when I read this in Honors English. It seriously fucked up my blissful, conservative Christian world. Our prof was notorious for giving terrible grades (to these students who thought of themselves as "honors" students), and looking back, he was actually right. Most of the students didn't actually want to engage with the difficult material he gave us; they weren't writing papers that actually engaged the material. He always said "I want you to learn how to think clearly". Anyway, Notes is kind of an exposition of self-consciousness within the context of the ever-increasingly impersonal modern world. It's the individual versus society; the Underground Man detests society but desperately hates himself for his inability or unwillingness to engage with it. Or at least, that's what I remember from it. I need to re-read it.
The Man Who Was Thursday by G.K. Chesterton. This is my favorite novel. It's utter genius, but you'll either love it or hate it. The philosophical aspects are hard to explain without basically giving away the story. What I love about this book is how many different ways you can interpret it. It's clear that, as a Christian, Chesterton is illustrating what he sees as the virtues of order and religion, versus what he sees as the self-refuting nihilism of anarchy (a real political movement at the time). But there's some truly beautiful surrealism and an addictive nightmare-quality to the entire narrative which pre-dates surrealism as an artistic movement. You can also interpret the narrative as a kind of "turning-inside-out", where surface appearance gives way to true reality. It almost has a mystical quality to it. There's also some totally confounding ways to interpret how Chesterton portrays God. And I almost forgot, the novel is also absolutely hilarious (if you've read any Chesterton, then you know what I mean).
Till We Have Faces by C.S. Lewis. This is Lewis's last and greatest fiction work. It's just pulsating with sorrow and regret and spiritual ennui. It's a retelling of the myth of Cupid and Psyche, told from the perspective of Psyche's ugly older sister Orual. Nothing like anything else he wrote. Again, without giving up the key plot points, this is probably the deepest interrogation into the nature of The Divine that I've read in fiction form. It was a transformational read for me. "I know now, Lord, why you utter no answer. You are yourself the answer. Before your face questions die away. What other answer would suffice? Only words, words; to be led out to battle against other words."
Four Quartets by T.S. Eliot. This is a long-form poem, about 60 pages or so. Not fiction. It's Eliot's masterpiece, to me. Not quite as arcane as The Wasteland. You really just need to read it, slowly, several times, over the course of a few years, preferably out loud. Only in sittings as long as you're able to ingest the words. I'm still slowly beginning to understand this poem, and I probably will continue to study it for the rest of my life.
“So here I am, in the middle way, having had twenty years-
Twenty years largely wasted, the years of l'entre deux guerres-
Trying to use words, and every attempt
Is a wholy new start, and a different kind of failure
Because one has only learnt to get the better of words
For the thing one no longer has to say, or the way in which
One is no longer disposed to say it. And so each venture
Is a new beginning, a raid on the inarticulate,
With shabby equipment always deteriorating
In the general mess of imprecision of feeling,
Undisciplined squads of emotion. And what there is to conquer
By strength and submission, has already been discovered
Once or twice, or several times, by men whom one cannot hope
To emulate - but there is no competition -
There is only the fight to recover what has been lost
And found and lost again and again: and now, under conditions
That seem unpropitious. But perhaps neither gain nor loss.
For us, there is only the trying. The rest is not our business.”