Did DFW have the sorts of insights or suspicions about how certain things in this world work and the liklihood of changing them that can be easily summed up as "cynical"? Of course he did. But I think that there is a definite reason why people react strongly to this word in relation to him. It is, for me at least, exactly and precisely the one thing more than any other thing whatsoever of the many things I love about his writing: he seems, to me, to have as his central point: to constantly strive to get to something beyond cynicism, something more connected than what seems at first the obvious response to all the involuted webs of corporo-politico-advertorial-tainment that rule the last few decades. He stands in relation to cynicism as a stance for living one's life or writing one's work in about the same place as he stands to certain strands of pomo literary cleverness. Basically, this is a guy who was well-versed in the most fragmented and/or pomo of literary fiction and pomo philosophy and theory and did his best to avoid not only the easy, reactionary denial of any of the insights that this fiction, philosophy or theory might have to say about our era and what it means to live in the immediate pre or post millinial moment ("Damn relativist commies! get off my lawn!"), but also, the harder to avoid lure of a certain cynical passivity that too easily seems to accept the need for connection or cohesion as un-hip passé projects. One way of interpreting much of his work is to see a guy who is deeply familiar with the theories of fragmented selves, elusive textual meanings, technological mediation of experience, etc. etc. and says "OK, so if all this is sort of a given, how do you go about the business of living (and creating) in a way that still values and strives for something other than the smug pleasures of ironic distance?" I think this shines through in just about every interview I've ever read/heard with him, but more importantly is, I think, successfully made flesh in his best writing, at the pinnacle of which, for me, is Infinite Jest.
ETA: of course better said by the actual quotes from DFW in the post above mine.
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