This book looks at Charlie Chaplin’s masterpiece, Modern Times (1936), through the lens of film aesthetics, structure, and post-modern perspective. The naïve Tramp character of Modern Times is often seen as the embodiment of a revolutionary reaction to his age. However, this study of the film shows that it is not only difficult but also impossible to accept the long-established critical reception of Chaplin’s film and its characters in our own "Post-modern Times." Drawing from extensive research and bringing post-modern context to the film through a comparative analysis of Todd Phillips’s Joker (2019), the book introduces how exhilarating a comprehensive study of film can be for engaged viewers. Illustrating that a detailed filmic reading of Modern Times can be a guide, or an extended case study, for analysing culture, this book will be of interest to students and teachers in film studies, literary studies, and the visual arts.