To be truly pretentious, you'll need:
Something short by James Joyce, say <i>Dubliners</i> or <i>Portrait of the Artist as a Young Man</i>.
<I>The Tin Drum</i> by Günter Grass.
Something short by Gabriel Garcia Marquez. The missus knows her Spanish, so I asked her, and she said something in Spanish that I think is the Spanish title of <i> No One Writes to the Colonel</i>. <i>The General in his Labyrinth</i> is the one I might suggest, though.
Sun Tzu, <i>The Art of War</i>. For a non military person to read it appears pretentious. If they are military, then Niccolo Machiavelli, <i>On War</i> is the pretentious choice.
Anything at all by Philip K. Dick. "The Nine Billion Names of God" is one, and <i>The Man in the High Castle</i> is the other. (<I>Do Androids Dream of Electric Sheep</i> is every bit as pretentious, but, because they made it into a movie with a much slicker name, no one notices that any more.)
Sylvia Plath, anything at all.
Ginsberg, "Howl".
<i>Mythologies</i> or <i>The Eiffel Tower</i> by Roland Barthes. There is nothing more pretentious than a French anthropologist trying to structurally analyze everyday life. (Actually, they're both pretty good reads too. 80 to 120 pages of one to 3 page essays. Good for the bathroom.)
<i>Mrs. Byrne's Highly Selective Dictionary of the English Language</i>, 200 pages of words everyone should know, but nearly no one does.
<i>The Transitive Vampire</i>, grammar made goth.
That's it for now
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