It's 1997 at the dawn of the digital age in San Francisco. Ex-journalist and struggling alcoholic David "Itchy" Crane's fledgling "information consultancy" business is getting slowly buried by bad luck, bad decisions, and the growing presence of the Internet. Before Itchy can completely self-destruct, a crooked private investigator offers him fifty grand to find a missing girl named Ashley. Crane takes the job because the money's right and because the only clue to her disappearance is a dead-on oil portrait of Crane himself painted by the mysterious missing girl--whom he has never met.
As Crane's search for Ashley rapidly becomes an obsession, he stumbles upon a series of murders, gets slapped around by thugs and intimidated by cops, and begins to suspect he's being framed for the murders by a psychotic Guatemalan hit man. Left with no avenue but survival, Crane goes on the offensive, fighting to clear his name, solve the murders, and find the beguiling portrait artist Ashley, who may have a few surprises of her own.