5) Once Bitten
Sometimes, you need a "horror" movie that's really just a dumb '80s comedy — maybe your boyfriend gets spooked too easily? — and tht's when Once Bitten is there for you. Starring an impossibly young Jim Carrey in his first leading role, like 90 percent of all dumb '80s comedies it's about a teenager (Carrey) desperately trying to lose his virginity. In this case, he runs into an ancient vampire (Lauren Hutton) who needs to drink the blood of a virgin three times before Halloween comes in order to stay young. The mix of dumb comedy and musty vampire tropes works surprisingly well, and apart from some cringeworthy gay-panic humor, it holds up surprisingly well. Okay, it holds up well for us old farts that were raised on this shit. As for the rest of you... well, you kids better just stay off my lawn, okay? I don't want to have to call your parents.
4) Donnie Darko
Is Donnie Darko really a horror movie? Depends on who you ask, but at the very least, it's pretty goddamn creepy at points, what with the mutilated bunny man running around dropping apocalyptic messages. It's also set on Halloween (hence the bunny outfit) — that climactic party is a Halloween party, lest you forgot — and it remains a great film to blow your mind while you get all dabbed up and enjoy your Halloween candy. It's also got an absolutely killer soundtrack, which is a nice bonus. Just avoid the director's cut, which over-explains everything and makes all the mystery of the original evaporate in a cloud of "Huh, that's actually kind of dumb" clarity.
3) Dark Night of the Scarecrow
Creepiest made-for-TV movie ever? Yep, creepiest made-for-TV movie ever. It's your basic supernatural revenge plot set in the ass end of nowhere — girl gets mauled by dog, mentally challenged gentle giant gets blamed, redneck idiots kill him for it. Except he's dressed as a scarecrow when he's killed, then comes back as a scarecrow with revenge on his (its?) mind and puts a world of hurt on those stupid rednecks. And makes friends with the little girl, who is somehow not creeped out by her returned-from-the-dead pal in his fucking creepy scarecrow getup. And, of course, it all takes place around Halloween, which I believe is the only time revenant scarecrows are allowed to get their revenge murder on. I saw this one as a kid — grandma assumed it would be fine, since it was on TV — and never forgot it. Now it's out on DVD, so you can relive my childhood trauma, or even inflict it on your own kids!
2) Trick 'R Treat
Now we're getting really Halloweeny! I've always had a great deal of affection for horror anthologies, and this one is all about Halloween. Four short tales of terror, woven together via a creepy little trick-or-treater with a rotten sack over his or her head, offer dire warnings about what can happen if you fuck with Halloween. Each is a study in what you can accomplish in very little time with a few good scares, and together they make for one hell of a Halloween movie. If you've never seen it, this is the year to fix that. If you have, well, I hardly have to convince you to watch it again, do I?
This can't be a surprise, can it? It's set on Halloween. It's called Halloween. Oh, and of course it more or less launched the slasher film into the pole position of horror for the next decade or so, which is no small feat. I'm pretty sure I don't have to recap the plot for most readers, but just in case, it's about a psychopath who kills his sister, then escapes an insane asylum years later to kill again. One of John Carpenter's signature films, and a true horror classic that can still make you a little uneasy about running around at night with so many people wearing masks...