The social structure is constitutively a space where people live together. Accordingly, it is a fact that representations of femininity and masculinity constantly exist in society. These relations are the behaviors that are acquired in consequence of specific cultural aspects and socialization processes. There are totally different representations of femininity and masculinity in different parts of the world. On the other hand, these representations are not fixed and have a structure that can differ in the course of time. Some culturally described characteristics of men and women have began to change in Turkey with social changes. Media and movies are spaces where the representations of femininity and masculinity are delivered and reproduced as role models. Although feminist studies are generally regarded as studies on women, there has been an increase in studies on masculinity in recent years. Masculinity studies emphasize that traditional patriarchal social structure are eroded in recent years and women become more effective in public space and professional life. In this respect, the argument, which the traditional male power has lost his power in the social sphere, becomes prominent. The decrease of male dominance is generally called “crisis of masculinity”. Acı Aşk (2009) directed by Taner Elhan and written by Onur Ünlü was chosen as a sample. Qualitative film analysis method and descriptive technique were used in the study. Acı Aşk was comparatively analyzed with the representations of masculinity in these two periods which were prominent in the history of Turkish cinema. In addition to that, the issues of masculinity and the crisis of masculinity in the film were examined in terms of power, sexuality, male-female relations, and economy. As a result, it appears that Acı Aşk has defined a different masculinity image than Yeşilçam films. In the film, masculine crises described in which the male character who establishes the relationship with women on the basis of power and authority.