These are my all-time favorites to set the spooky scene for Halloween. I will start off easy, and then get to the scariest!
Nightmare Before Christmas (1993). This one is animated but a Disney classic. The'Pumpkin King' of Halloween Town, Jack Skellington, accidentally ends up in Christmas Town and becomes mystified and intrigued with the Christmas holiday. Jack hatches a plan to bring Christmas to Halloween, but the villain of Halloween Town, Oogie Boogie, is all about sabotage. PG, 1 hour and 16 minutes in length. 95% on rotten tomatoes - my gosh, it's worth 100% to me. The scare meter is 1/10 - not scary. It's dark, but Disney at the end of the day.
Monster House (2006). Many might disagree with me here, but this is my second animated choice. The classic mean older man, get off my lawn, story starts with a 13-year-old named DJ and his friend kick a ball onto ole' Nebbercracker's property. The older man has a heart attack, and they quickly discover the house is a monster. After a courageous rescue of a friend, the trio of friends tries to convince the babysitter and others that the house isn't what it seems, to no avail. Now that I've said this, it seems silly, but it's just a well-made kid's spooky story. Great start to a haunted evening at home. Scare meter 2/10.
Hocus Pocus (1993). The story begins on Halloween night in the town of Salem. Max Dennison is new to town, and while trying to impress a girl, he mistakenly awakens three mischievous witches who have been dead for 300 years. Max & co. must stop the evil trio before it's too late. This movie is PG and 1 hour and 36 minutes in length. Rotten tomato score if only 37%, but to me - it's a cult classic and not too scary. The scare meter is 2/10 for me.
Beetlejuice (1988). A recently deceased couple find themselves in the attic of a home with an unbearable family. They befriend the Gothic teenage daughter and then hire a malicious spirit to drive them out of the house. PG, 1 hour, 32 minutes. Rotten Tomato score of 84%. It's another classic. The scare meter is 3/10.
The Craft (1996). A teenage girl moves to town and hooks up with a trio of witches. They practice witchcraft in hopes to use for revenge plots, but soon change focus for a quest for power. They soon learn that wielding power isn't what it's cracked up to be. Rated R, 1 hour, 31 minutes. Scare meter 5/10.
Fright Night (1985). A teen discovers a man who moved to the neighborhood and begins dating his mother is a vampire. He sets out to get help from an actor who starred in horror movies. I love this movie! 91% on Rotten Tomatoes. Scare meter 5/10. The film contains some jump scares and is supernatural, but this has some funny moments.
Sixth Sense (1999). A boy who has the gift to communicate with ghosts seeks the help of a child psychologist. PG-13, 1 hour, 37 minutes. This is an M. Night Shymalan movie - enough said. Watch it. 86% on Rotten Tomatoes. Scare meter 6/10. It's tense, supernatural.
Psycho (1960). This film is a classic. Period. It's B&W but get over that. A secretary steals 40K from her employer and goes on the lam, ending up at the Bates Motel. Hoping to meet up with her boyfriend with the loot, she meets the hotel's proprietor, Norman Bates, instead. Scare meter 6/10. It's a jump scare type thing and a bit psychological. 96% on Rotten Tomatoes. After this - go watch the television series - it's in my top ten of all-time TV shows.
Nightmare on Elm Street (1984). I'm not going to sugarcoat this - I haven't seen this since it came out. Oops. But I do remember this scaring the bejeezus out of me back then. I can't say this stands up the test of time and technology, but this is set in the early '80s when a psycho named Fred Krueger, the Springwood Slasher, has murdered several children with his razor-blade gloves. He dies but comes back to haunt and kill teens on Elm Street. 94% on Rotten Tomatoes, which says a lot for a horror movie.
Halloween (Rob Zombie version) (2007). A remake of the classic, but far improved. It's Halloween, 1963, and Michael Myers is a very disturbed child who ends up in a sanitarium for the heinous crimes he commits. Later, he breaks out, and you can guess what happens from there. Rated R, 1 hour, 49 minutes in length. Look - it has a bad Rotten Tomatoes score of 27%, but this one is better if you liked the original. Scare meter 7/10. I'm difficult to scare.