This article examines American performers who were billed as the ‘human fly’ in the decades around the turn of the twentieth century; a time when the term went from describing a type of theatre and circus act to the act of scaling public buildings in front of large crowds. This was a period of time when a new type of urban architecture, modern modes of advertising and publicity, the motion picture newsreel, and film stardom were all emerging, and all of these played a role in shaping the meaning of the human fly performance. Human flies appropriated tall buildings for their death‐defying acts, and their acts addressed changes taking place in the urban environment. Flies used modern skyscrapers to attract crowds and generate publicity, making this a performance that needs to be seen in terms of modern strategies of advertising and publicity. Additionally, the performances of the human fly played a role in the early film industry, first because they represented what Jennifer M. Bean has called a ‘competing logic’ of early film stardom, and second because stunt performers such as human flies figured in the development of the motion picture newsreel. In the course of the article, the author focuses on several ‘human flies’ who can illustrate how this performance changed over time. These include F.S. Sutherland, a turn‐of‐the‐century steeplejack who showed the potential of that modern labour as a form of entertainment; Rodman Law, a human fly, stunt performer and the subject of one of the first Pathe newsreels; and the ill‐fated Harry Young, a human fly who fell to his death promoting Harold Lloyd’s famous film Safety Last (1923).