It's the Great Pumpkin, Charlie Brown (1966)
This is the classic TV special from Charles Schulz. Completely family friendly and enjoyable for all ages.
Ghostbusters (1984) & Ghostbusters 2 (1989)
The first two Ghostbuster movies are goofy, cheesy funny ghost movies starring Dan Aykroyd, Bill Murray, and Sigourney Weaver. These films are fun and the ghosts make it relevant around Halloween. (Ghostbusters 2 is available on Hulu.com through Halloween.)Van Helsing (2004)
This fun monster film is based loosely on Bram Stoker's Dracula with other monsters from the classics (Frankenstein, Mr. Hyde...). The story is relatively intriguing but this movie primarily is fun. Hugh Jackman and Kate Beckinsale dealing with werewolves and Count Dracula in Transylvania is hugely entertaining.Signs (2002)
This M. Night Shyamalan flick is about a family who are first hand witnesses to an alien invasion. It stars Mel Gibson, Joaquin Phoenix, Macaulay Culkin's younger brother Rory, and Abigail Breslin. It has its creepy moments but mainly is a family film focusing on Gibson's character's loss of faith following his wife's death. It is pretty cool how it ends and I've always enjoyed this one.Disturbia (2007)
This Shia LaBeouf film is creepy and somewhat stupid at times, but your heart will pump hard if you get into it. I liked it even though the characters did some really stupid things at times.Halloween (1978)
This is a classic scary slasher movie starring Jamie Lee Curtis and seemingly based on Hitchcock's Psycho. It is creepy and very well done. Aside from walking into a dark house and not turning on the lights, I could connect well with the characters. The music is AMAZING and this film would be nothing without it. The piano melody really sets yours nerves on edge. Have a listen:
It is also available on Hulu through Halloween.
What movies do you like to watch on Halloween? Also, here is a clip from Community that gives great observation about scary movies: