Books: Catch-22, Hitchhikers Guide to the Galaxy series, Discworld, John LeCarre novels, Girl with the Dragon Tattoo, so many more...
Movies: Dr. Strangelove (when I went looking for it at Best Buy the clerk thought I was getting porn)...actually, cant go wrong with Kubrick... Brazil, hard to go wrong with Gilliam, Tarantino flicks are good too.
TV: Star Trek, recently started watching Dr. Who and its a shame that so many of the old episodes are lost. Scrubs was good. House is good. Metalocalypse, Venture Brothers. Evangelion.
Music: Well...mostly I am looking for the content behind the music. The lyrics are important. Phil Ochs, Midnight Oil, Rage Against the Machine, Neil Young. I tend towards rock, sometimes metal. Guitar music.