Doug (a hilariously chipper Cris Lankenau) went to school for forensic science (in the hopes of becoming a Sherlock Holmes type) but then dropped out because he "lost interest." Finishing out would have put him in a much better position than he is now, clinging to his sister (Trieste Kelly Dunn) and holding down a job at an ice factory. At work, he befriends Carlos (Raul Castillo, holding the screen in an excellent comic performance), a part-time DJ who laughs at first at Doug's aspirations at being a detective but comes to appreciate them.
You see, Doug's ex-girlfriend Rachel (Robyn Rikoon) is dropping into town for some reason and Carlos starts inviting her to do things (like go to a Star Trek convention, which Doug scoffs at). It's unclear what sort of relationship that Carlos and Rachel develop, as implications could go either way. Anyways, Rachel is a no-show for a DJing gig of Carlos' and he gets really anxious and solicits Doug's help to find out where she is.
From the point at which the two investigate the motel room in which she was staying until the end, the film makes little to no sense, and gladly so, as it is proving its point well. There is a briefcase of money, multiple identities, and a cowboy/porn photographer named Jim Warden involved, but how those dots are connected is beyond me. But, as I said, Doug jumps right in, making stops for a pipe and tobacco and for breaking a code of baseball statistics, much to the annoyance of his dragged-along sister. I will go and say now that there is no conventional resolution to the film, so as not to disappoint anyone, but if there was, it would offset Katz's vision (by leaving information limited to assumptions, he's making another comment about the whole detective business). Eliminating the film's deliberately slow start would be unfitting as well. It may be a bit tiresome, but we would see Doug in a much different way without it.
The acting and writing may strike some as bad. Personally, I think both are endearing. The eccentricities of the film (that often are present in movies of this genre) totally work, and the characters are always enjoyable to watch, as Lankenau, Dunn, and Castillo all play off each other exceptionally. The cinematography by Andrew Reed is jaw-droppingly good as well, especially in the scene set in a storage building. There's another passage that rests all on the camerawork, an exchange in the ice factory where we follow Doug back and forth from one wall to another while talking to Carlos. It absorbs you in a remarkable way. I doubt a lot of people will love this film, but to me, it's an observant work that knows how to treat its main character: supplying him with laughs, but also expressing a bit of disapproval at his lethargy and desperate attempts to free himself from it. B+