David Lynch
The director of Eraserhead, Blue Velvet, Wild at Heart, Twin Peaks, and The Lost Highway (among others), he is definitely the weirdest thing on this site. He movies are known for being VERY strange, surreal, and hard to understand. Some recurring themes in his films are stupid questions, long pauses between responses (in dialog), and useless, bumbling police. (See Chief Wiggum). Of course, those are just the stupider elements. Most of the stuff I've seen by him is very weird, and I like it. A David Lynch movie can affect you the way no other kind of media can. More on this later.
It should be noted that recurring themes in Lynch's films and 2-d art are dental hygeine, bald women, smoke, cross-dressing, and spark plugs.
David Lynch on the Tonight Show: A Transcript
Links:
Eraserhead FAQ- Finally all those illiterate people at school who see my Eraserhead shirt and ask "What is that, like a band or something?" (ignoring the words "A Film By David Lynch" under the title) will see what it is. Well, okay, they won't. But YOU will!