This film is based off of a story on the subreddit Let's Not Meet. A man takes a late night stroll and encounters an unsettling stranger. The video and story both do a great job of taking something as comforting as a smile and turning it into something sinister.
This short is creepy for a completely different reason than all the others on this list. There are no ghosts or demons, just a portal and a bit of primal fear. Be careful not to abuse the power you have.
Ugh, who in their right mind ever thought it'd be a good idea to make a childrens' toy in which a creepy-ass clown jumps out sporadically? ThIs short has no real plot to it, but it'll remind you why nobody likes Jack-in-the-Boxes.