College student Ashley and her new roommate, Roxy, go to a party hosted by a bunch of local hackers--think a RL 4chan party--and watch a viral video featuring "Smiley", a serial killer that (according to legend) stalks chat users and kills them if someone types in "I did it for the lulz" three times. Ashley's freaked out by the video; she's at least as freaked out that nobody else at the party seems terribly concerned about the person who just, you know, got killed on Youtube. "It's the internet," Roxy tells her, "who knows if it's even real?"
Judging by the initial trailer, Smiley seems like a modern slasher: trying to create a Freddy based on the internet instead of dreams. What we get is a critique of pure reason, a bunch of lectures about man's inherent nihilism, and a deep exploration of how people feel totally okay being assholes anonymously over the internet. It's a creepypasta movie centered around a hate meme, and--weirdly--it works.
It's not perfect; a lot of the acting is clearly "this is my first (or second) film", and a bunch of the plot was clearly dictated by having a college campus and someone's house as locations. A lot of the heavy lifting is done by Roger Bart, as the ethics professor who will legit end up an Unsub on Criminal Minds, and Keith David as a skeptical police detective. But I didn't see the ending coming, and--honestly, I like that the movie takes time to have four or five chats about ethics. It could be a little more tightly paced (we could have lost at least one Bart lecture), and the movie relies heavily on fake-out jump scares, but it's an interesting one. "Entertaining" is more up to the viewer.