I'm going to go against the grain and say don't listen to the people telling you reading philosophy texts is too hard. The only way it's going to get any easier is if you dive in! Sure, if you want to really understand it you're going to have to read, reread, and really think hard about it a lot of the time, but that's true of any text, really. Learning how to read philosophy, and getting a grounding in its historical arc, during my postgrad has honestly been one of the most life-changing things I've done, both because it's really changed the course of my life, but also because it's just really changed the way I think. Not necessarily what I think, but certainly how.
I suppose I would say that some philosophy is harder than others, but you just have to be prepared for what you are reading I suppose. Analytic philosophy can be very dry, but usually has a sensible, step-by-step structure that benefits from paying very close attention to it the first time through. Continental philosophy, and critical theory, tends to be a bit more dense, and the worst thing you can do is try to go through it with a fine-toothed comb the first time, as the shape of it is usually never really clear until the end, so it benefits more from just powering through once, making notes on what is unclear, and then a couple more readings trying to see how it fits together.
So anyway, I'm just going to dump a bunch of stuff that I've found interesting, and I'll try and group them sensibly and put them in an order that has some kind of through-line.
It's pretty valuable to look at some foundational philosophical texts, I think. Not necessarily classical texts, although Plato's Republic has pretty long fingers, particularly in the sphere of literature and art, although he touches on almost everything at some point. If you're interested in his view on art, then Ion is also interesting. Also worth looking at, just for it's silliness, is the Phaedo, just because it isthe most distilled example of the problems with Plato's dialogues.
But western Philosophy proper can probably be said to begin with Descartes, in particular his Meditations on First Philosophy and Principles of Philosophy. As well as containing his most famous quote, these texts are pretty much the first to lay down some kind of general method for undertaking philosophy. I think there's a lot of value in examining this because a lot of the principles in this debate have had a huge impact on our own era, with the ways in which science/technoology is becoming a very dominant force in our lives. Other interesting texts in this vein are John Locke's A Treatise Concerning Human Understandingwhich is probably more important, as it is a foundational text of empiricism. I've got a real soft spot for Hume's Enquiry Concerning Human Understanding which has interesting things to day about cause and effect.
As well as being interesting for the ways in which they shaped philosophy, what all these texts have in common are interesting takes on what we, as people, are. Ranging from a religious dualism to something approaching an evolutionary psychologists view with Hume's bundle theory. Other texts of interest in this debate are Rousseau's Discourse on the origin of Inequality... which nestled in with it's questions about property and contract law, contains an attitude to the truth of history which pops up in other places, notably Nietzche's Genealogy of Morals which also contains a celebratory denial of free will which is hard to wrap one's head around.
This way of interpreting history is really key to understand if you want to look at literary/critical theory in the twentieth century, particularly Foucault who writes in a very similar fashion. But since the move to literary theory marks a move from thinking about the self to thinking about art and culture, I'll just skip back a bit to recommend Kant's Critique of Judgment which is not the easiest text to read, and you might find problematic for a lot of reasons. Personally I've found it a very enlightening book in a variety of ways, but it may be all bollocks. It's probably mostly of interest for it's role bridging the gap between Pure and Practical reason, both of which might be worth a read as well, but it's also a good place to start thinking about what you believe art to be, so to speak, not in a "is x art" way, but in a "what am I looking at when I look at an artwork" way. You can pick this up again with Heidegger's The origin of the work of art (essay), which is a bit more explicit about those questions. It's also quite an enjoyable read. Also of value in this debate is Benjamin's The Work of Art in the age of Mechanical Reproduction which is as interesting for the assumptions he makes about the nature of artworks as it is for the central premise.
I was going to go into some more literary theory stuff, but it might be a little bit outside of your interest areas? The stuff I've put here is all, I think, related to ethics, free-will or culture. Critical Theory could probably be said to be interested in culture but I don't know how interesting it would be to you really. I will still recommend Roland Barthes' Mythologies which is a really easy-reading introduction to semiotics, and also Foucault's History of Sexuality Volume 1 (I don't think there are any more volumes) which is interesting because it shows how his attitude to history fits with Rousseau and Nietzsche, and also because it has a view of the sexual revolution that is a bit against the grain (and quite convincing to my mind). Perhaps instead of recommending any specific texts of literary theory, I'll recommend Clare Connors' Introduction to literary Theory, which is a really great book both because it relates everything back to literature (although theory is not always related strictly to literature, it's roots will always be literature), but also because it's a very friendly book that doesn't require a lot of specialist knowledge, but doesn't talk down to anyone who has it.
Anyway, sorry for the long post, but I do hope you find some interest in it.
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