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 50 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.