This thesis aims at comparatively analyzing the representation of financial capitalism in Wall Street (1987) and Wall Street. Money Never Sleeps (2010) with focusing on exploring in which ways the films promote/criticize the financial capitalism they portray. Theoretical approaches concerning film theories are mainly through ideological analysis, and supplemented by structuralist and semiotic theories. As methods used in data gathering and analyzing, basic film content analyses are principally applied through illustrating with film contents extracted from the films in qualitative and comparative ways in order to describe and distinguish the ideological positions of pro- and anti-capitalism in the two films. The results show an interesting fact that positions from the villain to the moral center are symbolized by both different characters separately and the key character (Gorden Gekko) alone. The analysis also shows that both of the films promote capitalism of freedom, which inspire people to work hard and create property for society, and criticize it of greed and immorality. However, Wall Street II is not nearly as merciless as the original, and it seems more fascinated than critical.