As the medium of film has become ubiquitous, it has become an influential vehicle for the transmission of gender-related values. Because gender portrayals in popular entertainment film play a role in the formation of social identity, and can affect human behavior, this thesis studies a group of popular American entertainment film's portrayals of their male and female characters. The method used to study the films, which were selected from the years 1950-2012, utilizes qualitative content analysis. The findings suggest that the female characters within the films studied broke old gender stereotypes more consistently than did their male characters. That said, there was some progress in terms of how some of the later films portrayed their primary male characters.