Fulfilled: A Halloween Story (15:53)
Halloween Short Films; IMDb; official website; YouTube

This was made in 1999. At the time... I knew someone who worked on the film. Part of me wants to explain that, even in vague terms, but a slightly stronger part of me... doesn't. In any event, I think I must have seen the film before it was officially released. Some time later (when I no longer knew anyone), I saw it on an episode of Exposure. But I'm writing this in 2018, after watching it again online for the first time in... nearly two decades, I guess. Damn.

Anyway. There's a makeup artist named Wayne. He makes a creepy scarecrow that he calls Ichabod. He has a friend named Samantha, who wants him to go to a Halloween party with her. But he doesn't, because he feels that people these days have basically desecrated the original spirit of the holiday. And he wishes every day could be Halloween. After doing Samantha's costume makeup for the party, she leaves, and he stays behind in his workshop to, you know, work on stuff. Late that night, he finally leaves to head home, taking a spooky shortcut. And Ichabod comes to life, and basically haunts him. I don't want to say how it all ends, but it's definitely disturbing. I don't know what else to say, except that I think it's a fairly well-made film.