Entertainment (2015)

To begin to understand a film as strange as Entertainment, you first have to understand Neil Hamburger.  Neil Hamburger is the alt-comedian persona of Entertainment star Gregg Turkington.  The closest comparison one can find for his act would be Andy Kaufman's Tony Clifton character.  In short, Neil Hamburger is the most offensively hostile comedian on the planet.  His jokes are either insulting, infantile, or in horrifically bad taste.  When the crowd isn't receptive to his brand of humour, Neil patronizingly urges the audience to 'put a smile on your fool faces'.  If this approach doesn't work, he moves to level two hostility, viciously targeting specific members of the audience with insults until they either retaliate or leave.
Entertainment follows Neil as he tours the Mojave desert, performing at various prisons and dive bars with his opening act, a clown/mime (Tye Sheridan) who specializes in only the crudest jokes possible.  Between shows, Neil takes stops to examine the few interesting areas of the desert, such as an airplane graveyard, or an abandoned car wreck.  He also calls and leaves messages to his estranged daughter each night and keeps her up with how things are going, though it's uncertain if she actually listens to these messages.  John C. Reilly features as Cousin John, who does his best to book shows for Neil, although he has difficulty understanding why he doesn't make his comedy more accessible to people. (much like the viewers themselves)
The cinematography and style of Entertainment owes a lot to the work of Stanley Kubrick.  (The Shining, in particular)  There are a great many long, almost glacially paced scenes, packed with uncomfortable silences from the characters.  One of the defining traits of Neil's character is that he almost never speaks a word when he's not onstage.  This is somewhat frustrating for a viewer who might want to understand his motivations, but I feel that it was a conscious directorial choice.  Another interesting choice is the sound of this film.  Many moments are punctuated with eerie, harsh white noise, which increases the strange feeling of dread and tension this film creates.
All of these stylistic choices add up to Entertainment's ultimate mystery:  why does he do it?  What good reason would a comedian have for sticking to such a controversial act, touring dead-end venues, and aimlessly wandering the desert?  Furthermore, is Neil suffering from a crippling depression, losing his mind, or is he simply bored to death?  Unfortunately, the film provides no true answers to any of these questions.  The film, much like its main character, simply exists.
Entertainment was nothing like what I expected it to be, but I think that's a good thing.  Certain scenes are very uncomfortable to watch, and the main character is barely likeable at all.  That being said, it is still well shot, and demonstrates good technique when it comes to filmmaking.