Philosophies of Ayn Rand, Bertrand Russell, Taoism, Zeno & Parmenides, and most metaphysics/epistemology issues, I also hate on religion quite a bit. Cause seriously, someone has to.
Edgar Allan Poe, and yes he's dead you sarcastic bastards. A realistic answer would be Trey Parker because he is a genius of our time. Billy Corgan would be interesting to know. Ayaan Hirsi Ali. Perhaps Dostoevsky so I could buy him a round. Lastly, I would like to meet Bertrand Russell so that I could give him a gun, and then see what he would do after Dostoevsky laid into his thang.
Radiohead, or Thom Yorke, Tom Waits, Billy Corgan, NIN, or Trent, System of a Down, old jazz (Ella F. etc..) because new jazz sucks, also anything dark that involves violin, oh and Aesop Rock and Maria Callas.
The Collector, Wings of Desire, Barton Fink, The Big Lebowski, Silence of the Lambs, Hannibal, Hannibal Rising,(Red dragon... ehh. ) Drop Dead Gorgeous, anything Trey Parker has touched, Halocaust films, To Wong Foo, Quills, Requiem for a dream, Secretary, Dead Man, Down by Law, Pleasantville, The Machinist, King of New York, I Heart Huckabees, Donnie Darko, Fear and Loathing in Las Vegas
South Park, the sexy Stewart and Colbert, Reno 911, old x-files re-runs, and Fox News for laughs.
"Eureka" by Eddy Poe, "We" by Zamiatin, "The Collector" by John Fowles, Brave New World-Huxley, The Great Gatsby, Frankenstein, The Fountainhead, Revolt of the Angels by Anatole France, all Henry Miller, First and last parts of Paradise Lost (because the middle needed an editor to step in), all Dostoevsky, Why I'm not a Christian by Bertrand Russell, Hannibal series by Thomas Harris, Life of Pi -Martel, Palahuniuk's Fight Club, A room with a view-Forster, Ayaan Hirsi Ali's The Caged Virgin and Infidel, Marquis De Sade, and David Sedaris.
Bill Hicks, Salvi Dali, Bertrand Russell, Ayn Rand, Dostoevsky, Trey Parker, Edgar A. Poe, Ayaan Hirsi Ali, Gandhi. Fictional characters include: Robert Jordon from For Whom the Bell Tolls, Howard Roark from The Fountainhead, Tyler Durden from Fight Club, Randle Patrick McMurphy from One Flew Over the Cuckoo's Nest, Frankenstein's monster, and Gatsby.