Our next movie set at Halloween is the cult classic Donnie Darko, one of the most confusing and surreal movies you'll ever see, but intriguing nonetheless. You can see why this became a cult phenomenon after it came out, since it's almost impossible to figure out what's happening in this movie and what it all means. Jake Gyllenhaal plays a troubled high schooler who keeps seeing a monstrous rabbit everywhere who's telling him the world is going to end in 28 days. This takes us through the month of October and a climactic Halloween party, which fits our theme, and the movie's creepy enough to qualify as somewhat frightening, although it's hardly horror. I wouldn't try to think too hard on this one when you're watching it- the plot is too puzzling to concern yourself with, so instead just enjoy the strange mood and dazzling visions set to some great 80's music (the movie takes place in 1988). It's still a haunting experience in a lot of ways.