When I realized who the writer/director was, it all made perfect sense..

As the same person responsible for "The Box" and "Donny Darko", Richard Kelly's career was always going to produce something like "Southland Tales." That is, he's a man of ambitious vision and daring unconventionality who lacks the patience and intellectual maturity to realize his vision properly. That was the problem with "The Box" and "Donnie Darko" and this movie exacerbates the issue by an order of magnitude.

I respect what he's trying to do. But Kelly needs to either hire a top-notch editor to clean up his thoughts so they bear less resemblance to the ramblings of a pot-addled undergrad, or take a step back and start following through on his own ideas. The movies mentioned in this post all had great potential. They just relied excessively on floating grand ideas and hoping no-one notices the lack of solid support underneath. The narratives collapse under the strain of trying to bring the audience to the thought-provoking denouement while skipping crucial intellectual/logical steps that would allow the structural elements to dovetail appropriately into the thematic ones. It's laziness, pure and simple. If you can't get from Point A to Point F without skipping Point C (for example), your grand vision is flawed and you need to work to make it work. Kelly, as of yet, doesn't seem to have the ability or willingness to make the effort. It's like a sloppy magic trick. Some in the audience will ooh and ah at the disappearing woman reappearing from behind the curtain. The rest, however, will wonder why the magician hoped we wouldn't notice the woman slipping out the back of the magic box.

As I said, this movie had potential, certainly. It hangs together by a thread. It just doesn't hang together nearly as well as he wants us to believe it does, and that's entirely on him, not the audience.