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This article presents how the act of falling has been used as a metaphor for invention within avant-garde art and aesthetics. It takes Lars von Trier’s documentary The Five Obstacles (2003) as its point of departure and seeks to historically contextualize the figure of falling by discussing Charles Baudelaire’s essay ‘De l’essence du rire et généralement du comique dans les arts plastiques’/‘On the Essence of Laughter’ (1955 [1855–1857]). The article also discusses the fascination with falling in early cinema, stressing how cinematic representations of the fall highlight the new medias potential for grasping general modern conditions like motion, speed and contingency. To think of art in terms of falling makes it possible to see a link between cinematic popular culture and so called high modernism. The article concludes with a discussion of the relationship between control and contingency within film aesthetics in the digital age. I will also discuss the aesthetics of Oulipo writers like George Perec and Raymond Queneau, and artists like Jackson Pollock and John Cage as exponents of what can be called an aesthetics of contingency.