This study aims to investigate the characterization of male gamblers in popular Hong Kong movies in the past 50 years. A total of nine Hong Kong films with gambling themes were selected for analysis. The criteria for selection of the films were as follows: the movies in which the protagonists are portrayed by well known Hong Kong actors that attracted a wide spectrum of the audience in the community. Out of such criteria, six male actors, each representing a legend at their times, were selected in the current analysis. Psychological analysis of the characters portrayed in the Hong Kong movies suggests a shift of the emphasis from the moral integrity and social responsibility to the individual pursuit of monetary gains as the dominant theme of the movie and a component of the characterization of the protagonists. Further, the particular cultural and social conditions of Hong Kong society in each decade may have significant bearings on cultural characterization of male heroes. We argue that the male characterization of gamblers in the Hong Kong movies might as well be a crystallization of public fantasies and wishes.