The Second City is as close as you can get to royalty within the comedy community. The vested troupe is the progenitor of pretty much all modern sketch comedy, and as such you'd expect any production involved with them would have an unassailable pedigree. This should be funny. God knows, watching it, it wants to be funny. A would-be writer whose script falls into the hands of a serial killer, who is in turn inspired by the script which gives the author a poorly founded sense of accomplishment. But while the basic plot might have been, at some point, a cute little idea for a dark comedy, the film that eventually developed from that idea falls flat.
There are other problems with the film, problems which I rarely make too large of a point of contention, especially with films at an independent level like this. The directing's not terribly inspired and the main actor isn't terribly funny, but little hiccups like that can be balanced out by other merits in the film. But the problems keep stacking as the film goes on. The writing itself isn't all that comedic, and the structure of the film seems extremely compartmentalized. There's no real flow to the story as it seems the writer was content to write individual vignettes and stack them in order rather than attempting to string them together. On top of that, we can add some bad lighting, unattractive cinematography, and some real glaring errors. In one scene in particular, the ambient noise includes a rainstorm, complete with intermittent thunder, without ever seeing rain on the screen. Instead we watch as the killer, played by Darrell Hammond in perhaps the only really fantastic performance in the film, professes his newfound love of the script he's just finished reading while a phantom thunderstorm constantly distracts you from any of the dialogue going on.
There are a ton of indie films that come out every year, and we're talking very indie films, that fit this same kind of formula, and they all stem from people assuming that anyone can sit down and write a comedy. The sad fact of the matter is, in this case, the script itself just isn't funny enough. It's not even attempting to be funny and failing, it just seems to forget that it's meant to be a comedy, even a dark one, and gets wrapped up in inconsequential storylines and scenelets that either don't lead anywhere or don't contain any actual jokes.
Looking back, there were maybe four or five moments in the film that the writers probably believed were their big belly-laugh moments, and those largely consist of dick jokes, the main character literally being showered in feces, and a recurring joke about the script our author keeps refusing to write suggested to him by his agent, a film called Black Santa (which is exactly what you think it is) and all the people he runs across believing that would be a fantastic film while finding his depressing. The poster image of the film is a man standing naked in the desert, where sure enough our hero is abandoned without clothes, and I almost want to believe the film was written around the idea for this one scene, which really isn't all that original or hilarious to begin with.
But I can't hate the film. There are movies out there that avidly insult the audience with how blatantly bad they are, with how little they seem to care about an audience's experience. It's clear that the filmmakers surely aren't all that experienced, and this level of inexperience is simply too much for a not-that-comedic comedy to survive. I'd hope that, as they keep working, these wrinkles get ironed out and we can see some real amazing stuff coming from Second City again.
Until then, I think I'll wait for Black Santa to come out. I hear it's amazing.