To make any contribution worth caring about, a philosopher's study of Shakespeare should do three things. First and most centrally, it should really do philosophy, and not just allude to familiar philosophical ideas and positions. It should pursue tough questions and come up with something interesting and subtle--rather than just connecting Shakespeare to this or that idea from Philosophy 101. A philosopher reading Shakespeare should wonder, and ponder, in a genuinely philosophical way. Second, it should illuminate the world of the plays, attending closely enough to language and to texture that the interpretation changes the way we see the work, rather than just uses the work as grist for some argumentative mill. And finally, such a study should offer some account of why philosophical thinking needs to turn to Shakespeare's plays, or to works like them. Why must the philosopher care about these plays? Do they supply to thought something that a straightforward piece of philosophical prose cannot supply, and if so, what? "Stages of Thought"
This brings us back to the theme of our previous post. Let's expand a bit, shall we? There are two perspectives we wish to examine: 1) how philosophy views literature and 2) how literature views philosophy. For now, we'll limit ourselves primarily to fiction.
1) From the philosopher's point of view, fiction is often useful. Philosophers are always looking for pithy aphorisms or apt metaphors to bring home their points and fiction writers and poets, because of their facility with language and image, often provide good illustrations. Fiction provides salient illustrations of abstruse points—but in an intuitive sort of way. Literary authors are seldom witting philosophers. There is an imperious view as well: fiction is something that can be used, for example, to confirm the philosopher's own philosophy or repudiate an opponent's argument. Through fiction, the philosopher can often demonstrate the power of his/her ideas. (The problem here, of course, is that fictional worlds stand in for real worlds and true experience.) And, finally, philosophy tries to make sense of things and the fictional work of art is one of the things the philosopher must ultimately make sense of. Philosophy asks such questions as what counts as knowledge? what does it mean to be? what does it mean to mean? how can we clarify things? what legitimate conclusions can we draw from a given set of premises? what, ultimately, underpins thought, reason, logic? is language thought? what is good, true, beautiful, right, just, etc? A philosopher might find a literary author touching around the edges of these questions but, in the end, must dismiss the effort as unsystematic or non-serious. Philosophy is about the life of the mind. A work of fiction is only useful so long as it is, in fact, useful to the philosopher.
2) From the literary point of view, philosophy is usually clumsy and poorly written. Boring. Abstract. Distant. Disengaged from reality. If a given novel or story is deemed to be merely the instantiation or embodiment of a philosophical doctrine then it is probably not a fully-realized work. It is hack work; its characters merely counters on a larger gameboard, its themes prefabricated, its "message" inauthentic. It is true that works of literature sometimes try to philosophize—e.g., the seven ages of man—but it is usually soft philosophy, not something widely respected or taken seriously among the pros. How can you falsify such a 'philosophy'? Certainly, writers can turn to philosophers to get an understanding of the nature of fiction or literature. What is its true function? its proper province? How best to understand or criticize literature? Fiction gives us insight into the life of the senses and the emotions, as well as the life of the mind, but as embodied in recognizably human characters. And what the writer of fiction does best is to humanize the philosopher and, importantly, and bring his/her philosophy down to earth. Who are these egg-heads and nerds, these geniuses and visionaries who provide us with these magnificent systems of insight? They are not gods, after all.
Drawing on our previous post, if art (in this case fiction) is the transfiguration of the commonplace (or, in Novalis's famous expression "renders the familiar strange and the strange familiar"), philosophy is the subsumation of the same.