This paper proposal explores the relationship of history and comedy in Joker (2019) through a comedy theory of broken thingness (Bergson 2003;Brown, 2001) and queer theory of failure (Edelman 2004; Halberstram 2011) -the interplay of the film's use of comic timing and signifiers of historical time in its diegesis. I argue that The Joker uses its black humour to probe a disjointed affective relationship to masculine dressage, and the repeating crises of a city coded as 1970s New York. While arguably courting the ironising nihilisms of the Alt-Right (Nagel, 2017), multiple points of disruption undercut a protagonist who is framed more as 'lucky fool' than 'canny trickster.' Repeated comic and diachronic failure, I argue, exposes the ambivalent thingness of postwar urban masculinity -critically, derivatively, problematically and foolishly.