Jason Robert Brown's musical, The Last Five Years, charts the tempestuous relationship between Cathy Hiatt, a struggling actress, and Jamie Wellerstein, aspiring novelist. The Last Five Years always appeared to be an unusual choice to make the transition from stage to screen. The film musical has always celebrated and relished the challenges presented in cinematically representing the 'genre's potential impossibility', nowhere better exemplified than in the artificiality of song, and spectacular dance numbers featuring endless chorus lines. Through considering the medium of film, modes of filmmaking and the subsequent impact these decisions have on the position of the spectator, the chapter analyses the ways in which Richard LaGravenese has approached transforming this material from stage to screen. The modes employed by LaGravenese allow the spectator to view the narrative from an entirely different perspective. The casting of the character, and the techniques and camera angles chosen by the director, present opportunities for an alternative reading of the character of Cathy.