This article contextualizes the work of William Burroughs in terms of twentieth-century avant-garde movements, particularly Dada, Surrealism, Lettrism, and Situationism, arguing that he was deeply influenced by them and also made significant and hugely influential contributions to their aesthetic and political projects. It situates his early work with the beats as markedly Surrealist, and it argues that Naked Lunch is a Surrealist masterpiece. It traces Burroughs’ movement into 1960s multimedia cut-ups, image-text, film, and audio experiments in relation to Guy Debord and Situationism. The article concludes by noting that we should be cautious in how optimistically we read some of this work, particularly in light of the many ways the twentieth-century avant-gardes failed to realize their revolutionary hopes and how our current experience with a fully-networked world that uses many avant-garde techniques and ideas often leads not to a utopian revolution but instead a morass of reactionary post-truth politics.