The aim of this paper is to discuss the decisive change in Stanley Cavell’s attitude towards the classical Hollywood cinema between The World Viewed (1971) and Pursuits of Happiness (1981). First, I will investigate Cavell’s earlier film philosophy regarding his analysis of the classical Hollywood cinema as mass culture. Cavell has been greatly influenced by the American critic Robert Warshow, and following his argument, we should regard the movies not as art but as “the bastard child of art” which could threaten or transform the concept of art. Secondly, I will discuss the concept of “creation of a medium” which Cavell introduced to the discussion of modern cinemas such as Nouvelle Vague in The World Viewed. For Cavell, “medium” means not just a material limit that forces artists to obey, but also a creative power of artist and/or critics. Cavell then applied this concept to the classical Hollywood cinema, and as a result, he recognized after the fact that Hollywood films have always been in a state of modernism. Finally, I will review Cavell’s later period, that is, his analysis of the classical Hollywood cinema as modernism, especially concerning the analysis of The Philadelphia Story (George Cukor, 1940) in Pursuits of Happiness.