In the grim days following WWII, San Francisco is a rough place to try and make a living as a private investigator. Nick Chambers is barely scraping by, only one step from sleeping in the gutter. When a peculiar man named Derek Halcyon offers to hire him to find someone Nick can hardly refuse, even when the only lead his client can provide is a single photo of his grinning quarry. Without even a name to go on, Nick begins a city-wide hunt for this mysterious missing person, and finds himself facing more questions than answers.

Based on the short story written by Keoni Chavez, originally published in the Nick Chambers anthology Fog City Nocturne, The Smiling Man pays loving homage to the classic detective films of the forties, while adding a decidedly post-modern slant.