The Moleskin Checklist is a detective-noir tale of a private investigator named Jack who does more chain-smoking and jazz record collecting than solving crimes. When Jack receives a disturbing package in the mail from criminals whose motives are unclear, he's reluctant to take action. But his mischievous lowlife friend Sappy - who tends to live his life as if he's in the movies - urges him to play this cinematic situation out to the hilt. They soon quickly learn, however, that real life is nothing like the movies and real villains do not behave as predictably as on TV.