'Alan Smithee' is a film about a boy growing up. It delves into the darker side of what 'growing up' sometimes means: growing into your flaws, inevitably being met with the errors of your parents, and the necessity to make room for the pain. While Alan is surrounded by what is thought to be the American ideal, all the material comforts that should equate happiness, he learns that sometimes all we are is lost in the woods.

Nate is a neurotic, recently laid-off investment banker. Joe is his unemployed, morally questionable, hustler roommate. Unable to find gainful employment (or pay for his impending wedding), Nate secretly tags along on Joe's work-for-hire Craigslist adventures. Each episode finds the unlikely pair doing an outlandish job for ridiculous people in an absurd attempt to earn a random buck.