I’ll update this list from time to time, but it’s what I have so far.  I’ll have to add more links, too.  These are in no particular order after than the top 5.

• “Illuminatus” Robert Shea and Robert Anton Wilson.
• “Stranger in a Strange Land” Robert A. Heinlein (also a former neighbor of my wife when she was a young girl).
• “Rape of the A*P*E” by Alan Sherman (“Hello Muddah, Hello Fadduh”).
• “Slaughterhouse 5” by Kurt Vonnegut.  Anything by KV.  Everything by KV.
• “Writing Down the Bones: Freeing the Writer Within” by Natalie Goldberg.
• “Catch 22” by Joseph Heller.
• “The Teachings of Don Juan” by Carlos Castaneda.
• “On the Road” by Jack Kerouac.
• “1984” by Orson Welles.
• “The Jungle” by Upton Sinclair.
• “Brave New World” by Aldous Huxley.
• “The Doors of Perception” by Aldous Huxley.
• “The Devil’s Dictionary” by Ambrose Bierce.
• “The Portable Dorothy Parker” by same.  I’m lucky enough to have a hard cover version of this.  Unsigned, sigh.
• Anything by William Shakespeare.  My favorites?  Macbeth, Othello, Romeo and Juliet, Hamlet, and Taming of the Shrew.
• “The Canterbury Tales” by Geoffrey Chaucer.  Yes, I know.  Yes.  Old to Middle English.  Settle down.  Breathe in through the nose, deeply now, let it out through your mouth.  Relax, it’s like Shakespeare, once you get into the swing of things, it’ll read like a Grisham novel.  Thank god you don’t have to read it in the original alphabet.
• “Decline and Fall of the Roman Empire” by Edward Gibbon.
• “A Doll’s House” by Henrik Ibsen.  It took a male writer to break the Bechdel Test barrier.
• “The Inferno” by Dante Alighieri. Try to think of who you know that will wind up in the place described.  Never fear, unless you are Catholic, hell does not apply to you.
• “Fear and Loathing in Las Vegas” by Hunter S. Thompson.
• The Bible (twice: once as a believer and once as a cynic).  Be able to quote it to both crowds for fun.
• The Holy Quran (and it’s companion “The Satanic Verses”)
• The Book of Mormon (and it’s companion “Under the Banner of Heaven”). Even if Mormons don’t read it (most don’t), you should.
• The Tibetan Book of the Dead.
• At least one sick joke book.  Be able to recall them on demand, especially at somber occasions, even if you don’t dare say them out loud.  Just don’t bust out laughing.
• “The Lord of the Rings”, “The Hobbit”, and “The Silmarillion” by JRR Tolkien.  Yep, I love them.  Have several versions on audio.  Hate the movies unless I think of them as entirely different stories than the books, maybe as tall-tale autobiographical inflations by the various characters: Legolas, Gollum, Aragorn, Pippin, etc.  I’m no longer bashing through imaginary dungeons (I’m in recovery) because of these books– who has time for that horseshit?
• For laughs:  “Atlas Shrugged” (or the condensed version “Fountainhead”).  If you identify with it stringently, you are an abomination.  If you jerk off to any of it, seek help.
• Junk: GRR Martin, Larry Niven, Charles Stross, more RA Heinlein.