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Exclude the philosophy books because much of philosophy is hard because highly technical, and exclude books that are called hard just because they are long, like "The FQ" (an unbelivably juicy book) and "Clarissa". Also exclude books that are hard because they play around with language in an allusive way, like "Finnegan's Wake" and most things by Gertrude Stein. That leaves books that are hard because what they are trying to convey in the best way they can is something elusive and subtle - "Nightwood" and "To The Lighthouse" fall into this - although I think "TTL" is pretty straightforward.
I would add some of the fictions of Maurice Blanchot, often very short but so difficult to construe that reading them is like trying to pick up a litter of greased piglets.
"Thomas The Obsucure" is pretty obscure, and "Awaiting Oblivion" shortens the wait considerably.
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