It should be understood before I list these that: a.) I don't enjoy horror movies, b.) I therefore haven't seen many, many classic horror movies (Halloween, The Omen, Rosemary's Baby, The Texas Chainsaw Massacre, Saw, etc.), and c.) this is a strange list because of a.) & b.). I think it can be fun to have a good scare every now and again to check your wits and reflexes, but who really wants to have nightmarish images branded in their mind?
1.) The Scariest Movie I've Ever Seen: The Shining (1980) - No question about it, the movie that scares me more than any other, even if I see it (and I try not to) on TV during the day with commercials. Anybody with me on this? The images of the twins and the butler and the hotel are just totally chilling, and I've always looked away before the decomposed lady comes out of the bathtub. Quite a collaboration between Stephen King, Stanley Kubrick - a master of bizarre creepiness - and Jack Nicholson. I even get a little nervous when I see "The Simpsons" spoof of this.
It (1990) - Serial killers on the loose and demon-possessed goblins are warm and cozy compared with clowns and dolls. Another Stephen King adaptation, starring Jonathan Brandis and John Ritter, It almost made me stop taking showers for fear that the clown would come up out of the drain. I remember there were pranks in the years following It where people in the neighborhood would dress up as clowns and creepily drive around or loiter at a little league baseball game or something. That's funny. An entire community of kids scarred for life.
Poltergeist (1982) - I don't think I saw any of the sequels to this, but the first one was enough - a killer clown doll, maggot-infested meat, haunted tree, a pool full of skeletons, and worst of all, a really short woman with the creepiest voice you've ever heard.
The Paper Boy (1994) - This only aired on the USA channel, so I think few people probably saw it even though it was on consistently for some time. Starring Alexandra Paul ("Baywatch"), it's about a really creepy teenage boy (Marc Marut) who is obsessed with being with her and will take whatever steps necessary, even dispatching his dad and the old lady/witch in the neighborhood. Marc Marut probably acted himself out of a career with his too-real performance, kind of like the kid in the Problem Child trilogy.
Child's Play (1988) - Fortunately, I don't even think I've made it past the first 20 minutes of this movie. I'm so scared of Chucky that when a preview for Child's Play 2 (1990) was on TV one afternoon and I was home alone, I bolted out of my house before it was even over, leaving everything on and the door wide open. Terrified, I ran to two houses in my neighborhood until someone let me in to wait until my mom got home. I was 9 or 10, and I was freaked out of my mind. My students loved to tease me about this story when I was teaching - thanks, Jill, for outing me. I can't even put the poster up here.
Ghostbusters II (1989) - Pretty funny, right? Ooooh, ghosts and bad guys with awful haircuts! Well when the weird museum guy (who is also the bad guy in Die Hard) morphed into a creepy ghost at the end, I literally went the entire night without sleep.
Jaws (1975) - Near the top of the list of my greatest fears in life is the deep sea - scary enough on its own, but a total nightmare when sharks are around, which I'm convinced they are no matter the body of water. The only really terrifying scene is the first one with the girl at night, but it's not like the rest is laughable or anything. I know I'm not alone in this - Jaws is basically the reason great white sharks are an endangered species. Steven Spielberg inadvertently set an entire generation of people on a mission to rid the world of them as soon as possible.
Carrie (1976) - Not sure when or how I first saw this, if I've even seen the entire movie, but I know I was pretty bothered by the blood dumping at the prom (?) and Sissy Spacek's dazed and disturbing appearance throughout the movie. Yet another Stephen King story - this guy is sick.
Psycho (1960) - Hitchcock's black-and-white classic didn't have extreme gore (chocolate syrup as blood), but delivered real horror with suspense and a creepy Norman Bates. I didn't see the remake starring a young Vince Vaughn. Can you imagine?
Seven (1995) - Brad Pitt and Morgan Freeman discover some of the most gruesome crime scenes you can imagine, the work of a demented serial killer (Kevin Spacey) who eventually beheads Gwyneth Paltrow. I can't remember exactly where it's supposed to take place (NYC?), but it's raining the whole time. One scene is particularly frightening, when the literally half-dead person jumps out of bed.
The Blair Witch Project (1999) - I saw this opening night back when I used to read reviews and watch trailers, so I knew it wasn't real. Nevertheless, I was chilled to the core by the children's voices and especially the last scene. Conveniently, I was staying overnight in a friend's windowless basement that night, and didn't sleep a wink. You have to give credit to this first-time filmmaking team.
The Exorcist (1973) - I'd never seen The Exorcist before going to the Boston Film Festival when the Director's Cut version was released a few years ago. Linda Blair, who plays the demon-possessed girl, was present at the screening for Q & A. We were told beforehand that she was running late but would be there by the time the movie was over. Well about halfway through, right after the horrifying backwards spider walk, a woman entered the theater and sat directly behind me, since my friends and I were in the back row. My roommate Shara and I looked back and looked at each other. The evil face on the screen was sitting behind us, surely spinning her head around right behind us. Needless to say, the rest of the movie was an unnerving experience. When the lights came up, the film festival person introduced Linda Blair to the audience, and a woman sitting on the complete opposite side of the theater stood up and walked to the microphone.
Deliverance (1972) - Burt Reynolds, Ned Beatty and Jon Voight in a gripping and disturbing tale of a canoing trip gone horribly wrong in Georgia. If you're familiar with "Dueling Banjos," this is where it's from - and it's really creepy, in addition to some other bizarre encounters in the woods. A Best Picture nominee that lost to The Godfather, Deliverance has suspense that you just don't find in movies any more, and it's scary because you believe that it could be a true story.
The Sixth Sense (1999) - M. Night Shyamalan's breakout film about a boy (Haley Joel Osment) who "sees dead people" is well written and expertly directed, with some very chilling moments - basically whenever we see the living dead. I especially had a hard time with the slit-wrist mother, the vomiting girl, and the shotgun-head boy. Fortunately, Shyamalan has since made only absolute nonsense, so I haven't had to have another terrifying theatre experience.
That's pretty much it. Feel free to list others that I haven't included (probably because I haven't seen them).