Seventeen-year-old Franz journeys to Vienna under Nazi occupation to apprentice at a tobacco shop. There he meets Sigmund Freud, a regular customer, and over time the two very different men form a singular friendship.

A series of snapshots from the life of a fictional actress named Shirley serves to weave together thirteen paintings by Edward Hopper (e.g. "Office at Night", "Western Motel", "Usherette", "A Woman in the Sun") into a fascinating synthesis of painting and film, personal and political history. Each station in Shirley’s professional and private life from the 1930s to 1960s is precisely dated: It is always August 28/29 of the year in question, as the locations vary from Paris to New York to Cape Cod.