Guest of Cindy Sherman takes an eye-opening look at what happens when a skeptical outsider finds himself romantically involved with the ultimate insider. Paul H-O became a fixture of the New York art scene in the 1990s with his public access show Gallery-Beat. Armed with a video camera, he attended art gallery openings, amusing some with his candid, witty assessments of their work, but also winning many fans. Among the latter was Cindy Sherman, the press-shy artist who is internationally acknowledged as one of the world's most gifted and significant visual talents. Cindy invites Paul to her studio for a series of exclusive interviews and through these videotaped encounters, he gains unprecedented insight into her artistic process and a romantic relationship blossoms. Their initial bliss ends when Paul finds himself wracked with anxiety about his own personality becoming subsumed by his role as Cindy's guest at the celebrity-studded openings and dinners she regularly attends. Filmed over 15 years and including interviews with a veritable who's who of the art and entertainment world (including Ingrid Sischy, John Waters, Robert Longo, Carol Kane, David Furnish, Danny DeVito, and Molly Ringwald), the film paints a vivid picture of the New York art scene that is also a witty, illuminating look at celebrity, male anxiety, and art.