Stanley Cuba has potential, or rather had. The writer/director Per Anderson has a great affection and admiration for Kubrick's films, but also his legacy in other things like photography and knows a good bit about his alleged personal habits. We see the references to the movies, of course, like a Dr. Strangelove caricature, lawyers/Papparazzi who come in Clockwork Orange garb, a red-eye ala HAL at an apartment door, masks ala Eyes Wide Shut, a few Sgt references from Full Metal Jacket, and a dog named Spartacus. But there's some obscurer touches, like Cuba in this film taking the picture of the man at the newsstand over the picture of Joey Ramone's death, as Kubrick in 1945 took his first picture that he sold of a man at a newsstand grieving over FDR's death. Or just the old, now well-crushed rumor about Kubrick's dislike of being driven anywhere over 30 MPH and with a helmet on.
He's a fan. But being a fan isn't quite enough. Making something with a good story, a point of view, is what counts. It's got a script that needed a whole lot of work, and it wasn't done before filming began. Too many times a joke won't just really work, or a reference will be there just for the sake of it. On occasion a joke does work well and can be very funny (i.e. the monolith, "This End Up"), or a random thing like the 'field' gag. But Mike Birbiglia also seems out of place here, not really sure in scenes of what to do or what the purpose is of things. Other actors look like the sort of New York non-union people that still need to hone their craft a little. Or, again, are mis-directed. Lines are funny, and you'll giggle here and there. Yet there's a reason you won't find it in most stores, or advertised, or, naturally, endorsed by the Kubrick estate. It's harmless, but stupid, and at best shot with competency and skill with digital video.