Charlie Chaplin is the actor and director most frequently mentioned in Benjamin's writings. From his articles on Soviet film in 1927 to the last version of ‘The Work of Art in the Age of Its Technological Reproducibility’ in 1939, Walter Benjamin consistently returns to Chaplin when discussing the potential power of film. Given the laudatory remarks that many intellectuals professed towards Chaplin, Benjamin's appraisal should not come as a surprise. Nonetheless, since Benjamin centres his analysis on the relationship of slapstick comedy and technology, it is puzzling why Benjamin does not also reference Buster Keaton, whose films are commonly replete with machines. Contrary to Chaplin, however, Keaton is at ease with technology and eventually manages—after a number of passages in which technology acts as if it has a life of its own—to use and transform machines and other technological utensils at his will. For this reason, Keaton can be seen as immune to the worst effects of industrialization, whereas Chaplin is its victim. Benjamin began to write about Chaplin at a relatively late stage. Apart from some small references, his first important text was a review of The Circus (1928), ‘Chaplin in Retrospect’, published in Die literarische Welt on 8 February 1929. The Circus was Chaplin's fourth full-length film after The Kid (1921), A Woman of Paris: A Drama of Fate (1923), and The Gold Rush (1925). There is a general consensus among academics that Chaplin's shorts, especially those directed for the Keystone, Essanay, and Mutual studios, are more transgressive than his feature films.