One of a very few academic papers on the music of Tom Waits, this essay reaches beyond well-trod discussions of Waits's persona that dominate trade interviews to assess Waits's chosen forms and media strategies as historically determined by the pressures of postmodern media and law. Locating in his music variations of the "estranging" function of what Waits' collaborator Keith Richards calls "the hair in the gate," this analysis explains how Waits' work has successfully eluded the deadening effects of a postmodern culture of consumption. In the latter sense, the essay suggests, Waits's work should be considered as part of an aesthetic beyond the merely "postmodern."