The documentary is about the 15 years of the career of one of the prominent American artists, Cindy Sherman. It covers the most comprehensive and sincere interviews with the artist that can be watched until then and takes the audience on a pleasant journey in the contemporary art world. The director of the film and the interviewer, Paul Hasegawa-Overacker, was one of the important figures in the art market in New York in the 90s. After his meetings to document Sherman’s life, he begins closely to observe her art production process, and their relationship turns into a love story. In time, their relationship deteriorates when Paul initiates to feel like a shadow of Sherman in the contemporary art world. After that, the film turns into Paul Overacker’s perspective of examining this relationship and leads him to question his ego and private life. The documentary which reveals this bitter-sweet love story humorously and sincerely offers the viewer enjoyable moments.