My nomination is for Ghost Hunt :) I really enjoyed it regardless of the time of year but I think it's a great supernatural anime to re-watch this October.
Some other spooky-themed ones come to mind about vampires like Vampire Hunter Saya. What other ones?
I think Death Billiards and Death Parade, Gyo, Jigoku Shoujo are kind of spooky animes. I don't think of Death Parade being scary other than the game parts, though. Gyo is a horror movie, not serie. When I think of vampires I always think of Hellsing (Ultimate version, not so much that other version) and Blood+ (is it same as Vampire Hunter Saya? Sounds like that to me).
Also when I first read the topic name I thought of Gugure! Kokkuri-san for some reason. I don't think it's spooky in any way, it's comedy.
Dainta's mentioned pretty much everything I could think of, with the exception of Vampire Hunter D. Other than that...If you haven't watched it already, maybe Gakkou Gurashi? There's some definite suspense and fear, even though it's mixed with typical anime silliness. I think Mirai Nikki might also be a good one.
It's a lot harder to think of anime that are scary or spooky in any way! The last thing I can think of is Monster. There are certainly a lot of horrifying things going on in Monster, though maybe not in a Halloweeny sense.
In addition to Hellsing Ultimate, Vampire Hunter D, and Blood+, here's a few others:
Blood the Last Vampire Blood-C Vampire Princess Miyu
A few horror ones: Another Boogiepop Phantom Higurashi no Naku Koro ni Requiem from the Darkness
That's just what I can think of off the top of my head. Gakkou Gurashi is great if you like zombie stuff.
Hm...For movies, if you just want weird and freaky, I'd always suggest Perfect Blue or Paprika. They aren't...-scary- but they have a feel of unease all around them. Same goes for Serial Experiments Lain. Like, what even is Lain. What.
For more traditional, most have already been said that I'd reccomend. Higurashi is great. So is Hell Girl. Death Parade. Etc.
If you want halloween-themes, but not scary-scary, Ghost Stories (english dub). It's terrible, and that's what makes it hilarious. And by terrible, I mean the voice actors ad-libbed most of their lines, and it becomes comedic.
Monster is another one that isn't fully halloween, but is very scary. It's almost...Hospital/Crime drama, but it's terrifying as all heck. Keep in mind, if you're a dub person (I don't judge), the dub wasn't finished due to the studio closing. Still a great anime though.
Dunno about anime, but a good cartoon movie is The Halloween Tree.
Shiki and Corpse Party: Tortured Souls are also pretty spooky and will put you in the mood for Halloween. :)
Blood The Last Vampire comes to mind, as well as Rosario Vampire. Rosario Vampire isn't really spooky, though, just goofy, but it has a lot of doofy Halloween-y monster people in it. :3 (Though I suppose by that token, you could add Monster Musume to the list, for reasons of goofy sexy monster shenanigans.)
The first thing that comes to mind is Junji Itou's work, but a lot of his stuff isn't spooky as much as it is weird. The movie Gyo was mentioned earlier and is an adaptation of one of his works, though it differs from the manga.
Ayakashi: Japanese Classic Horror Mononoke (not Princess Mononoke) Shiki Shinsekai Yori (more of a psychological story) Yami Shibai
If you want to go the supernatural but not scary route: Little Witch Academia Nastume Yuujinchou
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