This is one of those films that constantly seems about to spin out of control, but stays, however precariously, on track. It's been compared to After Hours (a film Lawrence Blume, the director, frankly acknowledges as a reference), but, aside from the fact that it mainly takes place in daylight, it's as much a sort of manic buddy movie. It also falls squarely in a sub-genre of films about impulse-driven characters taking more repressed ones in tow and leading them… somewhere. Zorba the Greek is probably the classic film in this line, but many more modern, often obscure films, such as Boxful of Moonlight come to mind as well.
Finally, it can be described as "Mike Leigh meets the Upright Citizen's Brigade", since that NYC comedy/improv group used Leigh's method of deriving a script from improvisations to develop what we see here. The use of (well-disguised) DV allowed a certain amount of improv during the shoot as well, though not, it seems, for the two main characters, a guilt-ridden designer of promotional characters (Ian Roberts) and his highly unorthodox therapist (Matt Walsh). The story? Well, it's more of a journey actually, colorful, comic and careening. Still a kind of climax is achieved in a grande finale in which a Desert Storm-damaged vet, a woman with father issues, two strippers, an unnaturally endowed football player and even the two main characters unite to save four little girls dressed as spare ribs from...
Well, that would be telling. Which is something this expertly off-handed yet relentless film never does.
(Oh, and not that they play this up, but the film includes cameos by Andy Richter, Tina Fey and Janeane Garofalo, and the strippers are played by Kim Raver - "Third Watch" - and Amy Poehler - "SNL".)