Annie Hall achieved international acclaim and cemented its place in film history when it won four Oscars in 1978, including Best Picture, Best Director, Best Actress, and Best Screenplay. Woody Allen’s masterpiece is often considered one of the funniest movies in the history of American cinema. The film can be examined on a number of levels, from artistic, theoretical, and historical perspectives. Cowie looks at the film in terms of its role as both a reflection of and major influence during the 1970s, which served as a critical time for Hollywood and the film industry. He also looks at the film as an expression of the filmmaker: Woody Allen. Woody Allen never denies that his role as Alvy Singer is somewhat autobiographical and Cowie uses this to analyze the features of Allen’s life and personality that can be derived from the film. Woody Allen harbors a sense of mystery and complexity, which makes many of his films, especially Annie Hall, the best insight to his true self. Cowie researches and analyzes the origins of Annie Hall both in terms of Allen’s motivations that led him to the story as well as the logistical factors that affected the making of the film. The significance of Allen’s relationship with Diane Keaton as well as his obsession with New York City are evident not only through the content of Annie Hall, but even more so when one looks at the development of the film. In addition, Cowie observes the artistic and cinematic features of Annie Hall, many of which he argues are derived from Ingmar Bergman as well as from vaudeville traditions of stand-up comedians. Finally, Cowie addresses the actual content of the film in terms of cultural meaning and its appeal to viewers. He looks at Allen’s rampant and blatant use of stereotypes and the role of such stereotypes in this film, as well as in many of Allen’s other films. Cowie argues that despite the use of these potentially offensive stereotypes, Annie Hall manages to maintain a universal and lasting appeal because of Allen’s willingness to reveal his vulnerability and insecurities to the viewer.