The Tell-tale Heart (1953)
This creepy take on the classic Edgar Allan Poe tale is my favorite horror short. I watch it every year around this time. The combination of the stark, surreal animation, discordant music, and James Mason's hushed, but intense narration are chilling in a harshly modern way. Now on the National Film Registry, it was a film ahead of its time.
Cross Roads (1955)
I love the cool vibe of this low-key British short starring Christopher Lee as a man who seeks revenge on the cad responsible for his sister's death.
They Caught the Ferry (1948)
A couple racing through the countryside on a motorcycle to catch a ferry encounters a terrifying supernatural force in this short directed by Carl Theodor Dreyer (Vampyr ). For most of the brief running time the film plays like a high-speed thriller, which makes its switch to horror all the more frightening. This version doesn't have English subtitles, though they are not necessary to understand the film. If you want subtitles, this version has them; it also has an added soundtrack, which is good, but I prefer the tension of the music-free original.
How a Mosquito Operates (1912)
While the IMDb classifies this Windsor McCay short as a thriller, it's obviously a horror film. It demonstrates how mosquitos are actually just little vampires flying around to terrify and annoy us. The repetition of movement and jerky style of early animation makes it extra creepy.
The Merry Skeleton/Le squelette joyeux (1897)
This early short from French film pioneers the Lumière Brothers is interesting because with the music the image of bones flying off and on a skeleton is amusing, but in silence, the one minute film is a bit unsettling.
The Haunted House (1908)
Played for laughs, this French short from Pathé studios is full of early special effects. Though no longer impressive, these cinematic tricks are still amusing.
The X-Rays/The X-Ray Fiend (1897)
It's under a minute, but this short about a couple who appear to become skeletons when an X-ray machine is pointed at them is another amusing look at the early use of special effects. At the time it was made, X-rays had only been in existence for a couple of years, so the concept and the way the technology worked were likely still mysterious to most audiences.
The Devil in a Convent (1899)
I had to include a Georges Méliès short, because the French film pioneer was the first major filmmaker to develop the concept of screen horror. His ghoulish sense of humor essentially set the template for the genre.
Spook Sport (1940)
For the avant-garde fan, this self-proclaimed "film-ballet" is an abstract version of the Danse Macabre featuring the music of Saint-Saëns. Canadian animator Norman McLaren got this effect by drawing directly on 35mm film.
Saint-Saëns: Danse Macabre Halloween Film Strip
This last short is actually a collection of images with musical accompaniment. Once again using Danse Macabre by Saint-Saëns, it is a series of spooky scenes meant to evoke the Halloween season. The YouTube comments on this one are a must-read. It seems a lot of people got the pants scared off of them watching this presentation at school as kids when it rattled through the film projector each year.
There's also a lot of great classic horror flicks streaming this month! My recommendations:
The Criterion Channel is featuring an eight film collection of Universal horror classics that is essential spooky season viewing.
Shudder is now offering a trio of 1970s horror classics featuring black stars: One of my favorite movies in any season: Sugar Hill (1974), in addition to Blacula (1972) and Scream, Blacula, Scream (1973).
HBO Max has so many great horror classics streaming right now that I'm only sharing a small portion of what they have to offer. This is definitely the channel to browse for spooky season delight. The collection includes: Eyes Without a Face (1960), Freaks (1932), Hausu (1977), Onibaba (1964), Mystery of the Wax Museum (1933), Equinox (1970), and The Blob (1958).
Netflix doesn't typically offer a lot of classic titles (as many film fans well know), but they are streaming the bonkers Exorcist III (1990) and Guillermo del Toro's Crimson Peak (2015), which has lots of lush period details which should appeal to film fans who can handle the (quite brutal) violence.
If you have access to Kanopy, the service always has lots of classic horror. My favorites: The Vampire Bat (1933), George Romero's underappreciated Season of the Witch (1972), When a Stranger Calls (1979), The House on Haunted Hill (1959), and The Old Dark House (1932).