This one is the quintessential "creepy painting", Henry Fuseli's "The Nightmare" (this is one of several versions).
While the swooning lady is wonderfully overwrought, the sheer terribleness of the squatting homunculous thing (Who incidentally has the same repugnant look on his face as this old woman on the bus I take into work who gets bent out of shape when anyone tries to sit next to her) and that messed up horse complete the gothic spectacle.
Then we have Henri Rousseau's "The Snake Charmer"...this painting impressed itself upon my childhood brain as many of Rousseau's paintings did...this one is unnerving because of the unnatural darkness of the character in the sunlight. That element along with the magical weirdness of the snakes (why is she calling them?) and forest created an palatably sinister aura (and it always made me think of a sasquatch, frankly).
What's hard to see in this image is the white eyes set into an almost featureless face...
Yikes.
This is a painting of our old pal, "Lucifer" by Franz Von Stuck. I find this image to be particularly unsettling because I'll have nightmares occasionally in which I sudden happen across some malicious demon creature peering at me intently and it often looks similar to this. I like this concept of "the devil" because it's much more frightening than some little red goat dude with a pitchfork. THIS guy looks formidable and evil.
And finally, we have "Calm Sea" by Arnold Bocklin. This one is great because it has that sassy red-headed mermaid rolling seductively around a rock, which is nice until you notice her underwater companion! Not as attractive as his lady friend. Once again- creepy staring!
