Funny and smart people. All things Hasselhoff! My family (even the unfunny ones.)
Socrates, Albert Einstein, and Thomas Jefferson in a dark alley for a knife fight.
Anything but Klezmer.
The Big Lebowski. Dr. Strangelove. Murder By Death. The Blues Brothers. Harold and Maude. Deep Blue Sea* (only with DVD commentary!)
Three's Company and 60 Minutes at the same time.
John Irving, Dr. Seuss, and Chris Ware. John Hodgman, Michael Palin, and Richard Dawkins.
Anyone who has strapped their ass to a rocket and gone into space. And my dad (despite his lack of space travel.)